source: Caselaw Access Project

author: THOMPSON, Circuit Judge. TORRUELLA, Circuit Judge

license: Public Domain

text:
    UNITED STATES, Appellee, v. Wendell RIVERA-RUPERTO, a/k/a Arsenio Rivera, Miguel Santiago-Cordero, Daviel Salinas-Acevedo, Defendants, Appellants.
    Nos. 13-2017, 13-2047, 13-2072
    United States Court of Appeals, First Circuit.
    January 13, 2017

      H. Manuel Hernández, Maitland, FL, for appellant Wendell Rivera-Ruperto.
    Ignacio Fernández de Lahongrais, San Juan, PR, for appellant Daviel Salinas-Acevedo.
    Camille Lizarribar-Buxó on brief for appellant Miguel Santiago-Cordero.
    Robert J. Heberle, Attorney, Public Integrity Section, Criminal Division, U.S. Department of Justice, with whom Juan Carlos Reyes-Ramos, Assistant United States Attorney, Nelson Pérez-Sosa, Assistant United States Attorney, Chief, Appellate Division, and Rosa Emilia Rodriguez-Vélez, United States Attorney, were on brief, for appellee.
    Before TORRUELLA, LIPEZ, and THOMPSON, Circuit Judges.
   THOMPSON, Circuit Judge.

In this appeal, Defendant-Appellants Wendell Rivera-Ruperto, Daviel Salinas-Acevedo, and Miguel Santiago-Cordero challenge various aspects of their trial and sentencing. For Rivera-Ruperto, this was his second of two trials, which were presided over by different district judges. Having separately addressed Rivera-Ruperto’s challenges from the first trial in a decision simultaneously released herewith, we address in this opinion Rivera-Ruperto’s challenges, as well as those of Salinas-Acevedo and Santiago-Cordero, as to the second trial only.

During trial, all three defendants were convicted of various federal drug and firearms-related crimes for participating in drug deals that were staged as a part of the FBI sting operation “Operation Guard Shack,” about which we say more in a bit. As a result of the convictions, each was sentenced to multiple years of imprisonment. In the present appeal, Rivera-Ru-perto raises similar challenges, which we detail momentarily, to those he raised in his appeal of his first trial and sentencing. As for Salinas-Acevedo, he argues the district court erred in preventing him from presenting an entrapment defense. Santiago-Cordero presses a similar argument, challenging the judge’s refusal to give an entrapment jury instruction, and also appeals the district court’s denial of his post-verdict motion for acquittal.

For the reasons stated below, we affirm.

OVERVIEW

We begin with a broad overview of the facts, and later return to the specific details of the case as they relate to the individual defendants’ arguments.

Operation Guard Shack, as we have explained in previous decisions, was a large-scale investigation mounted by the FBI over several years in order to root out police corruption throughout Puerto Rico. Each of the stings followed a similar pattern. Undercover FBI informants recruited police officers to provide armed security at drug deals staged by the FBI. The deals took place at FBI-monitored apartments wired with hidden cameras, and involved undercover officers posing as sellers and buyers of sham cocaine. In exchange for their armed security services, the police officers were paid about $2,000 per deal.

Rivera-Ruperto, Salinas-Acevedo, and Santiago-Cordero provided armed security at several of these Operation Guard Shack sham drug deals between March and September of 2010. Rivera-Ruperto, who was not a police officer (but who was recruited because he misrepresented himself to the FBI’s undercover informant as a prison corrections officer) provided armed security at six deals, which took place on April 9, April 14, April 27, June 9, June 25, and September 16 of 2010. Salinas-Acevedo and Santiago-Cordero, who were both police officers, participated in one deal each, on March 24, 2010, and July 8, 2010, respectively.

The government charged the three defendants with one count each of conspiracy and attempted possession with intent to distribute a controlled substance, as well as possession of a firearm in relation to a drug trafficking crime. (Various other co-defendants were also charged, but their cases are not before us.) In this indictment, Rivera-Ruperto was charged for his participation in the April 9 deal only. For his participation in the five later deals, Rivera-Ruperto had already been indicted separately, tried before a different district judge, and found guilty. The first judge sentenced Rivera-Ruperto to 126-years and 10-months’ imprisonment.

Several months after Rivera-Ruperto’s first trial, he, Salinas-Acevedo, and Santiago-Cordero were tried together in a second proceeding, which is the subject of this appeal. The jury found Rivera-Ruperto guilty of all charges, and Salinas-Acevedo and Santiago-Cordero guilty of the conspiracy and firearms counts (it did not reach a verdict for either of them on the attempted possession count). After separate sentencing hearings, the district judge sentenced Rivera-Ruperto to 35-years’ imprisonment to be served consecutively with his first sentence, resulting in a combined prison sentence from Rivera-Ruperto’s two trials that totaled 161 years and 10 months. Salinas-Acevedo and Santiago-Cordero were each sentenced to 15-years and 1-month imprisonment.

The defendants timely appealed. Rivera-Ruperto challenges various aspects of the trial and sentencing, and Salinas-Acevedo and Santiago-Cordero of the trial only. We discuss below each defendant in turn, beginning with Rivera-Ruperto.

DISCUSSION

I. RIVERA-RUPERTO

As we have previously noted, we issue today a companion decision to this case affirming the district court in Rivera-Ru-perto’s first trial and sentencing. Riyera-Ruperto’s challenges here are similar to those he raised in that first appeal. Specifically, Rivera-Ruperto argues that the district court in this second case committed reversible errors when it: (1) failed to conduct a sua sponte inquiry to determine whether Rivera-Ruperto had received ineffective assistance of counsel during the plea-bargaining stage; (2) gave erroneous jury instructions; (3) did not reduce his sentence on account of sentencing manipulation by the government; and (4) sentenced him to a grossly disproportionate sentence in violation of the Eighth Amendment. For the reasons we explain, each of these challenges fails in this second appeal, as well.

A. Lafler Claim

Rivera-Ruperto reprises a Lafler challenge that he made (and lost) in his first appeal, in which he argues that he received ineffective assistance of counsel during the plea-bargaining phase. See Lafler v. Cooper, 566 U.S. 156,132 S.Ct. 1376,1384,182 L.Ed.2d 398 (2012) (holding that a defendant’s Sixth Amendment right to competent counsel extends to the plea-bargaining process). Before getting to his arguments, we give a brief recounting of what happened below.

1. Background

We set what is quite the complicated stage by again reminding the reader that Rivera-Ruperto eventually stood two trials, which were presided over by different district judges. Before the first trial began, Rivera-Ruperto was represented by court-appointed attorney Jose Aguayo (“Aguayo”), who remained his lawyer throughout the plea-bargaining stage.

Aguayo attempted to negotiate a plea deal for all of Rivera-Ruperto’s charges across the six sham drug deals (though Rivera-Ruperto had been indicted separately for the charges). When the negotiations resulted in no plea deal, the first case proceeded toward trial, this time with Rivera-Ruperto represented by different court-appointed counsel.

Three days before that first trial was set to begin, Rivera-Ruperto’s second attorney filed a Lafler motion, alleging that Aguayo had provided ineffective assistance of counsel at the plea-bargaining stage. He argued that but for Aguayo’s deficient performance, Rivera-Ruperto would have taken a 12-year plea deal that the government had previously offered during negotiations, and he requested that the court order the government to re-offer that 12-year deal.

On the morning of the day the first trial was scheduled to begin, the presiding judge held an evidentiary hearing on the issue. After considering the testimony and documentary evidence, the judge denied Rivera-Ruperto’s ineffective assistance of counsel claim. For reasons that we explain in detail in our companion decision and will not rehash here, we have already affirmed the judge’s denial of Rivera-Ruperto’s La-fler claim as it pertains to his first trial.

Some months after the first trial and sentencing, Rivera-Ruperto, represented by the same attorney, stood trial a second time for the charged offenses stemming from his participation in the April 9 deal only. At no time did trial counsel request that the second judge consider the Lafler argument Rivera-Ruperto had raised and lost before the first judge. Therefore, no ineffective assistance of counsel claim was raised by counsel or ruled upon by the judge in this second case.

2. Analysis

On appeal, Rivera-Ruperto acknowledges that counsel during his second trial never raised the Lafler issue, but he argues that the trial judge should nevertheless have made a sua sponte inquiry and independent ruling on the ineffective assistance of counsel claim. The judge’s failure to do so, he claims, was reversible error.

Rivera-Ruperto never raised the Lafler issue before the second presiding judge, and we assume his claim was forfeited and not waived. We thus review the judge’s purported failure to make a sua sponte inquiry on the ineffective assistance of counsel claim for plain error. United States v. Sánchez-Berríos, 424 F.3d 65, 74 (1st Cir. 2005) (“[A] waived issue ordinarily cannot be resurrected on appeal, whereas a forfeited issue may be reviewed for plain error”.).

Reversal under plain error review is only proper if: (1) an error occurred; (2) it was obvious; (3) it affects the defendant’s substantial rights; and (4) it is sufficiently fundamental to threaten the fairness, integrity or public reputation of the proceedings. United States v. Delgado-Marrero, 744 F.3d 167, 184 (1st Cir. 2014). Rivera-Ruperto cannot succeed in meeting these requirements. Even assuming that he clears the first three of the plain error review hurdles, Rivera-Ruperto cannot clear the fourth, because he cannot show that the judge’s purported error was sufficiently fundamental to threaten the fairness, integrity or public reputation of the proceedings.

In order to meet this fourth requirement, Rivera-Ruperto would need to show that if the judge had made a sua sponte inquiry into his ineffective assistance of counsel claim, she would indeed have found that Rivera-Ruperto had received ineffective assistance at the plea-bargaining stage, and was therefore entitled to appropriate relief. But, for reasons we explain in great detail in our companion decision to this case, and which we will not belabor here, we have already determined, on de novo review, that Rivera-Ruperto was not entitled to Lafler relief, as he cannot meet the two-part ineffective assistance of counsel test laid out in Strickland v. Washington, 466 U.S. 668, 687,104 S.Ct. 2052, 80 L.Ed.2d 674 (1984). See Lafler, 132 S.Ct. at 1376. Specifically, Rivera-Ru-perto is unable to show either that Aguayo’s performance was defective or that, even if defective performance were to be assumed, it prejudiced him. Thus, any claimed error on the second judge’s part in failing to conduct a sua sponte Lafler inquiry did not threaten the fairness or integrity of Rivera-Ruperto’s proceedings, and reversal on this ground is not proper.

B. Alleyne Issue

We move on to Rivera-Ruperto’s appeal of the jury instructions at his second trial, the only one of Rivera-Ruperto’s claimed errors that we have not also addressed in our companion decision. Rivera-Ruperto challenges the jury instructions regarding the firearms charges only, so we focus our discussion accordingly. First, a discussion of what happened below.

1. Background

Before we begin, we pause to remind the reader that at his first trial, among other offenses, Rivera-Ruperto had been charged with and convicted of one count of possession of a firearm in relation to a drug trafficking crime for his participation in each of five sham drug deals (which occurred on April 14, April 27, June 9, June 25, and September 16 of 2010). Under 18 U.S.C. § 924(c)(1)(A), a defendant who is convicted of possession of a firearm in relation to a drug trafficking crime is subject to a mandatory minimum sentence of 5-years’ imprisonment on the first conviction, and then 25-years imprisonment for every subsequent conviction, id. § 924(c)(l)(C)(i), to be served consecutively, id. § 924(c)(l)(D)(ii). Accordingly, following the trial, the first district judge sentenced Rivera-Ruperto to a total of 105-years’ imprisonment for his firearms convictions (5 years for the first § 924(c) conviction, and 25 for each of the subsequent four convictions).

At the second trial, Rivera-Ruperto was again tried, among other offenses, for possession of a firearm in relation to a drug trafficking crime, this time for his participation in the April 9, 2010 drug deal only. Notable for Rivera-Ruperto’s purposes, the government did not introduce at the second trial any evidence of Rivera-Ruper-to’s prior § 924 convictions from his first trial. In addition, while the judge instructed the jury as to the elements of the firearms offense, neither the jury instructions nor the verdict form included prior § 924 convictions as an “element” of the offense, or otherwise made any mention of Rivera-Ruperto’s prior convictions. After deliberating, the jury found Rivera-Ruper-to guilty of all counts.

Prior to sentencing, Rivera-Ruperto filed a sentencing memorandum in which he argued that—notwithstanding his five previous § 924 convictions from the first trial—the judge should impose the 5-year mandatory minimum sentence for a first-time conviction under the firearms statute, and not the 25-year minimum for subsequent convictions. Rivera-Ruperto argued that the judge could not impose the “enhanced” mandatory minimum because the jury had not made a beyond-a-reasonable-doubt finding as to his prior § 924 convictions.

The judge disagreed, denying the request in a written order prior to sentencing. After a hearing, the judge imposed the 25-year minimum sentence for a subsequent § 924 conviction. Rivera-Ruperto now appeals.

2. Analysis

Because the sentencing memorandum Rivera-Ruperto filed before the district court preserved his Alleyne challenge, our review of his argument on appeal is de novo. See Delgado-Marrero, 744 F.3d at 184.

In order to explain Rivera-Ruper-to’s argument, we must first give a bit of background on the relevant case law. At the time of Rivera-Ruperto’s second trial, the rule was (and still is, as we explain in a moment) that “[ojther than the fact of a prior conviction, any fact that increases the penalty for a crime beyond the prescribed statutory maximum” is an element of the offense to be found by a jury beyond a reasonable doubt. Apprendi v. New Jersey, 530 U.S. 466, 490, 120 S.Ct. 2348, 147 L.Ed.2d 435 (2000) (emphasis added). In making this exception for prior convictions in Apprendi, the Supreme Court deliberately left undisturbed its holding in Almen-darez-Torres v. United States, 523 U.S. 224, 226-27, 118 S.Ct. 1219, 140 L.Ed.2d 350 (1998), which permitted the use of prior convictions to enhance sentences without a finding by the jury.

Between Rivera-Ruperto’s trial and sentencing, the Supreme Court decided Al-leyne v. United States, — U.S.-, 133 S.Ct. 2151, 2155,186 L.Ed.2d 314 (2013), in which it held that the Apprendi rule applied not only to facts that increase the mandatory maximum sentence, but also to those that increase the mandatory minimum (thus overruling its prior holding in Harris v. United States, 536 U.S. 545, 568, 122 S.Ct. 2406, 153 L.Ed.2d 524 (2002), which had limited Apprendi to the former). The Supreme Court explicitly stated, however, that its decision would leave untouched Almendarez-Torres’s “narrow exception” for prior convictions. Alleyne, 133 S.Ct. at 2160 n.l.

Despite this language in Alleyne itself, Rivera-Ruperto argues before us that Al-leyne made Almendarea-Torres inapplicable to his case. He seems to argue that, because Alleyne expanded the Apprendi umbrella, bringing facts that increase mandatory mínimums under its shelter, we should, in keeping with the spirit of Al-leyne, limit Almendarez-Torres to its facts and determine that only prior convictions that increase the prescribed maximum are exempt from the Apprendi rule that such facts be found by a jury. Because his prior convictions increased the prescribed minimum, Rivera-Ruperto argues, they should be subject to Alleyne’s requirement that they be found by a jury beyond a reasonable doubt.

But this is not the law. As we have already explained, this was not the Supreme Court’s holding in Alleyne. Moreover, we have already rejected, in a post-Alleyne case, the argument that pri- or convictions must be proven to a jury beyond a reasonable doubt. See United States v. Rodriguez, 759 F.3d 113, 122 (1st Cir. 2014) (holding that the jury was not required to make a finding as to the defendant’s prior convictions because Al-mendarez-Torres remained good law). We therefore find no error.

C. Sentencing Challenges

Rivera-Ruperto’s remaining two challenges concern his sentence. He argues, as he did in his appeal from the first trial, that the government engaged in improper sentencing manipulation, and that his sentence across the two trials, for a combined 161-years and 10-months’ imprisonment, violates the Eighth Amendment’s prohibition on cruel and unusual punishment. In raising these arguments in the present appeal, Rivera-Ruperto incorporates by reference the sections of his brief from his appeal in the first trial. As we have already discussed these arguments in detail in our companion decision, we keep our recounting of what happened concise.

1. Background

At the first trial, the jury found Rivera-Ruperto guilty of five counts each (one for each of the five charged drug deals) of conspiracy and attempted possession with intent to distribute 5 kilograms or more of a controlled substance and of possession of a firearm in relation to a drug trafficking crime. It also found Rivera-Ruperto guilty of one count of possession of a firearm with an obliterated serial number.

At sentencing, Rivera-Ruperto argued that the FBI’s use of “large” quantities of sham cocaine at each of the drug deals, its request that he bring a firearm to each of the deals, its decision to allow him to participate in multiple deals, and its decision to charge him separately for each of the deals all constituted improper sentencing manipulation because, he claimed, the government made those choices for the sole purpose of exposing him to an enhanced sentence. The first district judge disagreed, and sentenced Rivera-Ruperto to 126 years and 10 months for the crimes.

At his second trial, Rivera-Ruperto was again found guilty, this time of one count each of three crimes (for the remaining April 9 drug deal only): conspiracy and attempted possession with intent to distribute 5 kilograms or more of a controlled substance, and possession of a firearm in relation to a drug trafficking crime.

After a sentencing hearing, during which Rivera-Ruperto’s counsel did not raise a sentencing manipulation objection, the second district judge sentenced Rivera-Ruperto to the statutory minimum of 10-years’ imprisonment for the conspiracy and attempt counts and the statutory minimum of 25-years imprisonment for the firearms count. Rivera-Ruperto was thus sentenced to a total of 35-years’ imprisonment, to be served consecutively to his 126-year and 10-month sentence from the first trial.

2. Sentencing Manipulation

Because Rivera-Ruperto did not raise a sentencing manipulation challenge before the second district judge, we review for plain error. See Sánchez-Berríos, 424 F.3d 65 at 78.

Rivera-Ruperto argues that the government engaged in sentencing manipulation by using unnecessarily high quantities of sham drags during the deals, requiring Rivera-Ruperto to bring a firearm with him to each of the deals, and then allowing him to participate in a “seemingly endless” number of those deals. We need not tarry in our consideration of Rivera-Ruperto’s sentencing manipulation argument here. In our companion decision, we explain in detail why Rivera-Ruperto’s fact-determinative sentencing manipulation argument fails under a clear-error standard of review. In renewing his challenge as to this second trial, Rivera-Ruperto has added no new argument, choosing merely to incorporate by reference the sections of his brief from his first appeal. Because Rivera-Ru-perto has adopted his briefing from the first case wholesale, the only difference in our review here is that the more rigorous plain-error standard applies. Given that Rivera-Ruperto’s sentencing manipulation challenge failed under the less exacting standard in the first case, it also fails here.

3. Eighth Amendment

The same is true of Rivera-Ruperto’s final challenge: his argument that his total sentence from the two trials of 161-years and 10-months’ imprisonment violates the Eighth Amendment’s prohibition on cruel and unusual punishment. Here, Rivera-Ru-perto again adopts by reference the Eighth Amendment section of his brief in the first appeal, which fails for the reasons we have already explained in our decision in that case. For the reasons stated in our companion opinion, Rivera-Ruperto’s sentence is affirmed.

II. SALINAS-ACEVEDO

We turn now to Salinas-Acevedo’s appeal. As we noted above, Salinas-Acevedo was indicted on charges of conspiracy to distribute and attempted possession with the intent to distribute more than 5 kilograms of cocaine, as well as of possession of a firearm in furtherance of a drug crime, for his participation in one Operation Guard Shack deal on March 24, 2010. The jury found Salinas-Acevedo guilty of the conspiracy and firearm counts, but did not reach a verdict as to the attempted possession count. Salinas-Acevedo was sentenced to a total of 15-years and 1-month imprisonment.

Salinas-Acevedo raises just one argument on appeal. He argues that the district court erred in preventing him from presenting an entrapment defense at trial. We begin with a discussion of what happened below.

A. Background

1. Lead-Up to the March 24 Deal

On March 24, 2010, fellow police officers Salinas-Acevedo, Alwin Camacho (“Camacho”), and Israel Rullán-Santiago (“Rullán-Santiago”) provided armed security at an Operation Guard Shack drug deal. What Salinas-Acevedo did not know at the time was that Camacho was working undercover as an FBI informant to recruit corrupt police officers for Operation Guard Shack.

Camacho had targeted Rullán-Santiago after he heard Rullán-Santiago bragging around the station that he knew drag traffickers and was “basically a delinquent using up the uniform.” It was Rullán-San-tiago who, in turn, recruited his friend Salinas-Acevedo. Both Rullán-Santiago and Camacho were aware that Salinas-Acevedo had a daughter and was expecting another child, and that he was in a difficult financial situation.

Originally, Salinas-Acevedo was supposed to participate in a drug transaction that had been planned for March 10, 2010. But, according to a recorded telephone conversation between Rullán-Santiago and Camacho on the night before that deal, Salinas-Acevedo, seemingly referring to his child, backed out at the last minute, telling Rullán-Santiago, “Sorry, it’s gonna be difficult for me because of the little girl and the like.” Hearing that Salinas-Acevedo would not make it to the deal, Camacho postponed the scheduled transaction.

Shortly thereafter, Camacho was also recorded talking to Carlos Méndez-Pérez (“Méndez-Pérez”), yet another police officer who would himself participate in Operation Guard Shack and be charged separately in a different case. During the conversation, Camacho brought up Salinas-Acevedo. Camacho asked, “[S]ince you’re buddies with Salinas, what do you think about Salinas?” He went on to say, “Because, um, Rullán approached him and later he gave me excuses that his daughter. ...” Camacho told Méndez-Pérez that Rullán-Santiago had told him that Salinas-Acevedo was “willing to do anything and he’s broke.”

Camacho also told Méndez-Pérez that he had directed Rullán-Santiago not to “bring up that topic with [Salinas-Acevedo] anymore.” But later in the conversation, Camacho told Méndez-Perez to talk to Salinas-Acevedo and have him “come by” to see him. In response, Méndez-Pérez told Camacho that he would stop by Salinas-Acevedo’s house. Camacho instructed Méndez-Pérez to find out what days Salinas-Acevedo “ha[d] available,” but also directed Méndez-Pérez, “[I]f he gives you a lot of crap[;] ... [t]his isn’t compulsory, this is for those who want to and know what it is.”

On March 19, 2010, in another recorded phone conversation with Rullán-Santiago, Camacho directed Rullán-Santiago to “get that guy that you tried to find last time,” by which he meant Salinas-Acevedo. Rul-lán-Santiago responded, “[L]et me see if, ... if that dog is around here.” Camacho replied, “Well, but let me know for sure, don’t do the same shitty thing to me like you did last week.”

Three days later, Camacho, who by then presumably knew Salinas-Acevedo had agreed to the job, called Rullán-Santiago to “double check[]” that Rullán-Santiago and Salinas-Acevedo were both on board for the upcoming March 24 drug deal. In a not-entirely-clear exchange, Camacho asked Rullán-Santiago, “You told Salinas what it was, right, the devices?” Rullán-Santiago at first told Camacho ‘Yes,” but then laughed and told Camacho that Salinas-Acevedo would “jump off the balcony when he sees [the drugs].”

The story ends, as we know, with the deal going down as planned, with Rullán-Santiago and Salinas-Acevedo being arrested and brought up' on charges, and with Salinas-Acevedo standing trial.

2. Lead-Up to Trial

Before trial, the government moved in limine to preclude Salinas-Acevedo from raising an entrapment defense in his opening statement. The district court initially denied the motion, but when the government filed a motion for reconsideration of the order, the trial court ordered Salinas-Acevedo to proffer his evidence supporting an entrapment defense.

Salinas-Acevedo proffered the following. First, he asserted that, at all relevant times, Camacho had been aware of Salinas-Acevedo’s difficult financial situation because Salinas-Acevedo had previously-asked Camacho about part-time opportunities at CompUSA, where Camacho worked as a part-time security guard, and Camacho had told Salinas-Acevedo that he would let him know if any opportunities opened up. Second, Salinas-Acevedo submitted a transcript of the recorded conversations between Camacho and Rullán-San-tiago and Méndez-Pérez, which Salinas-Acevedo argued showed that Camacho had targeted and incited Salinas-Acevedo into participating in the sham drug deals.

Finally, Salinas-Acevedo alleged that he had been wrongly induced into committing the crime because RuMn-Santiago had told him that the March 24 transaction was a “legitimate business transaction” involving the sale of diamonds, and that it was only after he had arrived at the location that it was revealed to him that it was a drug deal. However, at the court’s subsequent prompting, Salinas-Acevedo conceded that he did not have any evidence that the government (through Camacho) had directed Rullán-Santiago to tell Salinas-Acevedo that it was a legitimate transaction, or that Camacho was otherwise responsible for the alleged misinformation.

By sealed ex parte order, the court held that this was an “insufficient basis to allow defendant Salinas to mention to the jury in opening statements a defense of entrapment,” and vacated its previous order denying the government’s motion in limine. Accordingly, Salinas-Acevedo was not permitted to mention entrapment in his opening statement.

At trial, over the objections of Rivera-Ruperto and Santiago-Cordero (our third co-defendant in this appeal, who we will get to know better shortly), the district court declined to give the jury an instruction on the entrapment defense. Salinas-Acevedo did not join in that objection to the jury instructions. Salinas-Acevedo now appeals, arguing that the district court erred in preventing him from raising an entrapment defense.

B. Analysis

The government argues that Salinas-Acevedo neither requested an entrapment instruction, nor joined in his co-defendants’ jury instruction objection during trial, and that his claim is therefore unpre-served and subject to plain error review. See United States v. Guevara, 706 F.3d 38, 46 (1st Cir. 2013). Salinas-Acevedo argues that our review is de novo, presumably on a theory that his objection to the government’s motion in limine was sufficient to preserve his objection to being denied a jury instruction on entrapment as well. But even assuming, favorably to Salinas-Acevedo, that the claim was properly preserved, the argument still fails under de novo review.

The judicially-created doctrine of entrapment exists “to prevent ‘abusef ]’ of the ‘processes of detection and enforcement ... by government officials’ who might instigate an illegal ‘act on the part of persons otherwise innocent in order to lure them to its commissions and to punish them.’ ” United States v. Díaz-Maldonado, 727 F.3d 130, 137 (1st Cir. 2013) (quoting Sorrells v. United States, 287 U.S. 435, 448, 53 S.Ct. 210, 77 L.Ed. 413 (1932)) (alteration and omission in original). A defendant seeking to present an entrapment defense at trial must satisfy an “entry-level burden of production.” Sánchez-Berrios, 424 F.3d at 76. He must produce “evidence which fairly supports the claims” that: (1) the government agents not only induced the crime but did so improperly, and (2) that he was not already predisposed to commit the crime. Id. at 76-77.

In determining whether a defendant has met this two-part burden, a court “is to examine the evidence on the record and to draw those inferences as can reasonably be drawn therefrom, determining whether the proof, taken in the light most favorable to the defense can plausibly support the theory of the defense.” United States v. Gamache, 156 F.3d 1, 9 (1st Cir. 1998). If the defendant succeeds and the defense is introduced at trial, it becomes the government’s obligation to prove beyond a reasonable doubt that no entrapment occurred.

We begin by examining whether Salinas-Acevedo has satisfied the improper inducement prong of his two-part burden. Because Salinas-Acevedo did not deal directly with Camacho—the “government agent” in this case, see United States v. Luisi, 482 F.3d 43, 53 (1st Cir. 2007) (explaining that an individual hired as a government informant constitutes a government agent for entrapment purposes)—but was brought into the deal by a middleman (Rullán-Santiago), Salinas-Acevedo must rely on a derivative theory of entrapment. Under this theory, the conduct of a middleman is only attributable to the government where:

(1) the government agent specifically targeted the defendant in order to induce him to commit illegal conduct; (2) the agent acted through the middleman after other government attempts at inducing the defendant had failed; (3) the government agent requested, encouraged, or instructed the middleman to employ a specified inducement, which could be found improper, against the targeted defendant; (4) the agent’s actions led the middleman to do what the government sought, even if the government did not use improper means to influence the middleman; and (5) as a result of the middleman’s inducement, the targeted defendant in fact engaged in the illegal conduct.

Luisi, 482 F.3d at 55.

Salinas-Acevedo' satisfies the first two of these requirements. The recorded conversations proffered by Salinas-Acevedo show Camacho more than once asking Rullán-Santiago and Méndez-Pérez about Salinas-Acevedo, and encouraging them to get Salinas-Acevedo involved in the drug deals. Viewing the evidence in the light most favorable to Salinas-Acevedo, a jury could conclude that Camacho targeted Salinas-Acevedo and used at least Rullán-Santiago, if not both middlemen, to induce him to participate in the March 24 transaction.

In order to meet the third requirement, however, Salinas-Acevedo must show that the government (via its agent Camacho) encouraged Rullán-Santiago to employ a specific “improper” inducement. Id. The key issue here is whether a specified improper inducement by Rullán-Santiago (or Méndez-Pérez) can be attributed to the government itself. The government would be responsible for any improper inducement by either middleman if its agent (Camacho) had “told” or “instructed” the middleman (Rullán-Santiago or Méndez-Pérez) to apply the inducement later deemed improper. See United States v. Rogers, 102 F.3d 641, 645 (1st Cir. 1996) (“Under the case law the government would be responsible if [its agent] told [the middleman] to apply the pressure or inducement later deemed improper, and perhaps if [the government’s agent] knowingly tolerated it, but not if [the government’s agent] were ignorant of it.”); Luisi, 482 F.3d at 55.

For example, in Rogers, a government agent was introduced to a third-party middleman who engaged the defendant in a conspiracy to purchase drugs with the intent to sell. The defendant argued that the middleman should be treated as an “unwitting government agent.” Rogers, 102 F.3d at 645. We disagreed, finding that there was insufficient evidence associating the government’s agent with any improper inducement by the middleman. Id. We specifically noted that even if the middleman did act improperly, nothing in the record demonstrated that the government agent “urged, suggested, or was even aware of’ the improper conduct referenced by the defendant. Id.

Similarly, here, the record negates a finding of improper inducement by the government itself (via its agent, Camacho). On multiple occasions, Camacho told his intermediaries not to pressure Salinas-Acevedo to participate in the drug deals. While Camacho repeatedly asked the middlemen to check on Salinas-Acevedo’s availability and willingness to participate, there is no evidence that he urged them to apply improper pressure on Salinas-Acevedo to join the enterprise. To the contrary, Camacho specifically directed Méndez-Pér-ez that “if [Salinas-Acevedo] gives you a lot of crap[;] ... [t]his isn’t compulsory, this is for those who want to and know what it is.”

And although Camacho did direct Rul-lán-Santiago to get Salinas-Acevedo (“that guy that you tried to find last time”) to participate and Rullán-Santiago responded that he would see “if that dog is around here,” Camacho never insisted that Rullán-Santiago do whatever it takes to get Salinas-Acevedo to participate. Instead, Camacho’s reply—“don’t do the same shitty thing to me like you did last week”— appears to be a warning about adequate notice, given that Rullán-Santiago had backed out of the first transaction at the last minute and Camacho wanted Rullán-Santiago to let him know “for sure”—one way or another—whether Salinas-Acevedo would participate. Salinas-Acevedo must show not only that Camacho, through his middlemen, gave him the opportunity to commit the crime, but also a “plus” factor—an inducement amounting to some kind of “government overreach.” Guevara, 706 F.3d at 46. Even if we were to assume that actions of the middlemen here were improper, Salinas-Acevedo has failed to produce sufficient evidence of government overreach or arm-twisting in this case.

Salinas-Acevedo has thus failed to meet the improper inducement prong of his two-prong burden, and we need not proceed to the second question of whether he was already predisposed to commit the crime. The district court did not err in denying Salinas-Acevedo an opportunity to present an entrapment defense.

III. SANTIAGO-CORDERO

The last of the three defendants in this appeal, Santiago-Cordero, participated in an Operation Guard Shack drug deal on July 8, 2010, and was tried for one count each of conspiracy to distribute and attempted possession with the intent to distribute more than 5 kilograms of cocaine, as well as possession of a firearm in furtherance of a drug crime. The jury found Santiago-Cordero guilty of the conspiracy and firearm counts, but did not reach a verdict as to the attempted possession count. For his crimes, Santiago-Cordero was sentenced to 15-years and 1-month imprisonment.

Santiago-Cordero raises two issues on appeal. First, like Salinas-Acevedo, he appeals the district court’s ruling denying him a jury instruction on an entrapment defense. Second, he appeals the district court’s denial of his motion for acquittal. We start again with what happened below.

A. Background

This has, by now, become a familiar scene with a familiar cast of characters, so we will do our best to keep our narration short. Camacho and Rullán-Santiago reprise the same roles here that they played in Salinas-Acevedo’s story, as confidential FBI informant and unsuspecting middleman turned co-defendant, respectively.

As he had done with Salinas-Acevedo, Rullán-Santiago (with Camacho’s blessing) recruited Santiago-Cordero for an Operation Guard Shack drug deal. Camacho was apparently aware in the lead-up to the deal that Santiago-Cordero was money-strapped, because during the phone calls in which they discussed bringing Santiago-Cordero on board, Rullán-Santiago told Camacho that Santiago-Cordero was in need of money.

On July 8, 2010, as planned, Santiago-Cordero arrived with firearm in tow at the apartment where the sham drug deal would take place. Unaware that he was being surveilled by the FBI, Santiago-Cordero provided security services at the deal, where undercover officers posing as drug dealers exchanged sham cocaine bricks for large amounts of cash. After the deal was completed, Santiago-Cordero was paid $2,000. This was all caught on film.

Santiago-Cordero was arrested shortly thereafter, charged, and stood trial along with Rivera-Ruperto and Salinas-Acevedo. During trial, the prosecution introduced testimony from Camacho, as well as the video footage of the deal.

Toward trial’s end, the court held a jury charge conference. There, counsel for Santiago-Cordero requested that the jury be instructed on an entrapment defense, which the judge denied. After deliberations, the jury found Santiago-Cordero guilty of the conspiracy and firearm counts, but did not reach a verdict as to the attempted possession count.

About a week after trial, Santiago-Cordero filed a motion for acquittal, in which he argued that his conviction should be vacated because the evidence had been insufficient to support the jury’s verdict on the conspiracy count. The judge denied the motion, and, after a sentencing hearing, sentenced Santiago-Cordero to 15-years and 1-month imprisonment. Santiago-Cordero now appeals both the sufficiency of the evidence and jury instruction issues.

B. Analysis

1. Sufficiency of the Evidence

Santiago-Cordero argues, as he did in his motion for acquittal below, that both his convictions should be overturned because: (1) the government presented inadequate evidence at trial to support a guilty verdict on the conspiracy charge, and (2) without the conspiracy conviction, there was no “drug crime” on which his conviction for possession of a firearm in furtherance of a drug crime could be based. Because Santiago-Cordero preserved his sufficiency of the evidence argument, we apply de novo review. See United States v. Adorno-Molina, 774 F.3d 116, 121 (1st Cir. 2014).

In order to return a conspiracy conviction under 21 U.S.C. § 846, the government must show that: “(1) a conspiracy existed; (2) the defendant had knowledge of the conspiracy; and (3) the defendant knowingly and voluntarily participated in the conspiracy.” United States v. Maryea, 704 F.3d 55, 73 (1st Cir. 2013). Here, Santiago-Cordero takes issue with the “knowledge” element, arguing that at trial the government presented insufficient evidence that he knew the transaction involved the distribution of drugs. He contends that the video footage shows that drugs were never explicitly discussed during the transaction, and that he never looked inside the wrapped packages to confirm that they, in fact, contained drugs. He also argues that Camacho testified at trial that he did not know what Santiago-Cordero had been told about the transaction by Rullán-Santiago, and the government never put Rullán-Santiago himself on the stand. Thus, he claims, the government’s evidence was insufficient to prove beyond a reasonable doubt that he had knowledge of the nature of the conspiracy.

But a jury verdict will not be overturned so long as we find that a rational factfinder could have found that the evidence presented at trial, “together with all reasonable inferences, viewed in the light most favorable to the government,” established each element of the offense beyond a reasonable doubt. United States v. Poulin, 631 F.3d 17, 22 (1st Cir. 2011). Given this difficult standard, defendants raising this claim are “rarely successful,” United States v. Moran, 984 F.2d 1299, 1300 (1st Cir. 1993), and Santiago-Cordero is no exception.

To sustain a conspiracy conviction under § 846, the government “need only prove that the defendant had knowledge that he was dealing with a controlled substance, not that he had knowledge of the specific controlled substance.” United States v. Woods, 210 F.3d 70, 77 (1st Cir. 2000). Here, the government introduced at trial ■video footage of Santiago-Cordero, who the jury knew was a trained police officer, showing up for the July 8 deal armed with his firearm and ready to provide security.

Santiago-Cordero frisked the undercover buyer upon arrival at the deal site, and then watched as a substance packaged in bricks and marked with logos (in the same manner as cocaine is usually packaged) was exchanged for cash. See United States v. Azubike, 564 F.3d 59, 65 (1st Cir. 2009) (explaining that where the jury was shown evidence that “the modus operandi of the crime was the same as that of drug transactions sadly common in this geographic area,” this “supported] the jury’s conclusion that defendant knew he was transporting drugs”). Santiago-Cordero was then paid $2,000 for what amounted to less than an hour of work.

The government also presented the jury with a recorded phone call in which Rullán-Santiago told Camacho that he had informed Santiago-Cordero that they would be working a drug deal, as well as footage from the July 8 deal in which Camacho asks Santiago-Cordero, “Rullán already explained it to you?,” and Santiago-Cordero answers in the affirmative. On this evidence, a jury had a more than adequate basis to come to its conclusion that Santiago-Cordero had knowledge of the nature of the conspiracy. We thus affirm.

2. Entrapment Defense

We turn to Santiago-Cordero’s appeal of the judge’s denial of an entrapment defense instruction. Because he raised the objection below, our review is de novo. See Azubike, 564 F.3d at 64.

Having already mapped out the doctrine of derivative entrapment in our previous discussion of Salinas-Acevedo’s appeal, we keep our discussion of Santiago-Cordero’s entrapment argument short. Recall that a defendant is only entitled to an entrapment defense if he can establish the government agents improperly induced a crime that he was not already predisposed to commit. Sánchez-Berríos, 424 F.3d at 76-77. Here, the only evidence that Santiago-Cordero has produced of improper inducement is that the government knew he was “broke and needed money,” and that the government knew that its middleman, Rullán-Santiago, was a “delinquent” and used him anyway to recruit Salinas-Aeeve-do.

Awareness on the part of the government of a targeted defendant’s difficult financial situation does not, without more, constitute improper inducement. See, e.g., United States v. Baltas, 236 F.3d 27, 37 (1st Cir. 2001). As for Santiago-Cordero’s suggestion that using Rullán-Santiago as a middleman despite his shady reputation somehow constituted improper inducement, this misses the mark, too. As we explained above, the focus in an improper inducement inquiry is on the government’s tactics for recruiting the defendant. Rullán-Santiago may have been of disreputable character, but Santiago-Cordero has not identified any specific conduct on Rullán-Santiago’s part, whether at Camacho’s behest or otherwise, that constitutes improper inducement. Thus, Santiago-Cordero did not meet his burden of production on an entrapment defense, and was not entitled to an instruction at trial.

CONCLUSION

For the reasons we have stated above, we affirm.

TORRUELLA, Circuit Judge

(Dissenting in Part).

The majority holds that, as a matter of law, repeated suggestions cannot give rise to a defense of entrapment. I respectfully dissent. The purpose of sting operations is to bring willing perpetrators to justice, not to induce law-abiding citizens to err. Repeated suggestions are precisely one way to induce law-abiding citizens to err—especially where, as here, those law-abiding citizens are in dire financial straits.

Because the majority has already laid out the facts of this case, I summarize only the key facts here. Salinas-Acevedo was in debt, had a little daughter, and another child on the way—his financial situation was difficult, to say the very least. Both the government agent and the middlemen knew this. Still, Salinas-Acevedo showed great reluctance to become involved in any illegal drug transaction. The middleman had to approach Salinas-Acevedo multiple times in order to induce him to participate in the drug transaction. Although Salinas-Acevedo initially agreed, he later pulled out of the transaction on account of his little girl. It was only after being approached by the middleman again that Salinas-Acevedo finally gave in and reluctantly participated in the drug transaction. The middleman’s actions were all on the direct instructions of the government agent. Indeed, the final instructions of the government agent to the middleman were “Hey, get that guy,” “find, find that guy,” and, once more, “[fjind that guy”—all referring to Salinas-Acevedo.

I agree with the majority that we are here faced with derivative entrapment, and that the test for that has five prongs:

(1) a government agent specifically targeted the defendant in order to induce him to commit illegal conduct; (2) the agent acted through the middleman after other government attempts at inducing the defendant had failed; (3) the government agent requested, encouraged, or instructed the middleman to employ a specified inducement, which could be found improper, against the targeted defendant; (4) the agent’s actions led the middleman to do what the government sought, even if the government did not use improper means to influence the middleman; and (5) as a result of the middleman’s inducement, the targeted defendant in fact engaged in the illegal conduct.

United States v. Luisi, 482 F.3d 43, 55 (1st Cir. 2007).

I also agree with the majority that the first two prongs of this test are satisfied— but unlike the majority, I believe that the third prong is satisfied as well.

The majority takes great comfort in the fact that‘“[u]nder the case law the government would be responsible if [its agent] told [the middleman] to apply the pressure or inducement later deemed improper, and perhaps if [the government agent] knowingly tolerated it, but not if [the government agent] were ignorant of it.” United States v. Rogers, 102 F.3d 641, 645 (1st Cir. 1996). The majority then reasons that there are no indications that the government agent engaged in any improper inducement; the majority emphasizes that even if the middleman somehow did engage in improper inducement, then there is no indication that the government agent had told the middleman to do so.

However, “examples of improper ‘inducement’ ” include the use of “ ‘repeated suggestions’ which succeeded only when the defendant had lost his job and needed money for his family’s food and rent.” United States v. Gendron, 18 F.3d 955, 961 (1st Cir. 1994) (Breyer, C.J.) (quoting United States v. Kessee, 992 F.2d 1001, 1003 (9th Cir. 1993)). In the present case, the government agent told the middleman to engage in exactly this kind of improper inducement, for the government agent told the middleman to approach Salinas-Acevedo repeatedly about the drug transaction, knowing full well that Salinas-Acevedo had serious difficulties providing for his family, and that he had declined to participate numerous times.

Other circuits have also found that repeated suggestions constitute improper inducement for entrapment purposes. See United States v. Mayfield, 771 F.3d 417, 435 (7th Cir. 2014) (en banc) (holding that improper inducement “may be repeated attempts at persuasion”); United States v. Kessee, 992 F.2d 1001, 1004 (9th Cir. 1993) (“[The government agent] induced [the defendant] to sell narcotics by repeated entreaties, which only became successful when [the defendant] had lost both his jobs and desperately needed the money ... A jury could have had a reasonable doubt as to inducement or lack of predisposition”); United States v. Burkley, 591 F.2d 903, 915 (D.C. Cir. 1978) (“[T]he trial judge correctly issued an entrapment instruction because (1) [the government agent]’s repeated requests constituted sufficient evidence of inducement”).

It is not surprising that our sister circuits have come out this way, because the Supreme Court has found entrapment (even as a matter of law) where repeated suggestions were involved.

Retracing the Supreme Court’s key entrapment cases may help illuminate the problem ... In Sorrells the Court found that an entrapment instruction was warranted ... the informant’s persistent appeal to military camaraderie qualified as a potentially entrapping inducement. [Sorrells v. United States, 287 U.S. 435, 441 [53 S.Ct. 210, 77 L.Ed. 413] (1932).] In Sherman the Court found entrapment as a matter of law ... the inducement there consisted of repeated requests from an informant posing as a fellow recovering addict who had fallen off the wagon. [Sherman v. United States, 356 U.S. 369, 371 [78 S.Ct. 819, 2 L.Ed.2d 848] (1958).] In Jacobson the Court found entrapment as a matter of law ... the inducement in that case was a two-year campaign of fake mail-order entreaties conditioning the defendant to believe that child porn was acceptable and encouraging him to purchase it. [Jacobson v. United States, 503 U.S. 540, 546-47 [112 S.Ct. 1535, 118 L.Ed.2d 174] (1992).]
... [In each of these cases] [t]he entrapment defense was available because the government’s solicitation of the crime was accompanied by subtle and persistent artifices and devices that created a risk that an otherwise law-abiding person would take the bait.

Mayfield, 771 F.3d at 434 (emphasis added).

In sting operations, the Government should know when to take “no” for an answer, lest, as here, the “Government’s quest for conviction leads to the apprehension of an otherwise law-abiding citizen who, if left to his own devices, likely would have never run afoul of the law.” Gendron, 18 F.3d at 961 (quoting Jacobson, 503 U.S. at 553-54, 112 S.Ct. 1535) (emphasis added in original).

I respectfully dissent.

      . See, e.g., United States v. Navedo-Ramirez, 781 F.3d 563 (1st Cir. 2015); United States v. González-Pérez, 778 F,3d 3 (1st Cir. 2015); United States v. Diaz-Castro, 752 F.3d 101 (1st Cir. 2014).

      . The government raises a threshold argument that, because Rivera-Ruperto had already obtained a ruling on the Lafler issue in the first case, he was collaterally estopped from raising an identical issue in his second trial.
      Collateral estoppel, often referred to as issue preclusion, traditionally barred civil litigants from relitigating an issue that had already been decided in an earlier action. But it has also become an "established rule of federal criminal law,” and “is a part of the Fifth Amendment’s guarantee against double jeopardy.” United States v. Collazo-Aponte, 216 F.3d 163, 198 (1st Cir. 2000), vacated on other grounds by 532 U.S. 1036, 121 S.Ct. 1996, 149 L.Ed.2d 1000 (2001). As such, our case law has permitted the use of collateral estoppel in criminal cases—at least insofar as it is invoked by the defendant to prevent the government from relitigating a previously-decided issue. See id.
      The parties disagree over whether collateral estoppel may be used here, by contrast, offensively against Rivera-Ruperto. Indeed, we know of no case in our circuit, and the government points us to none, in which we have used collateral estoppel to prevent a criminal defendant from raising an issue, as the government would have us do in this case. We need not decide this issue today, however, and will not. As we explain, even if we assume, favorably to Rivera-Ruperto, that he is not collaterally estopped from raising his La; fler claim, the claim still fails.

      . The verdict form, which Rivera-Ruperto did not object to, simply stated: "We, the Jury, find defendant WENDELL RIVERA RUPER-TO _ (GUILTY/NOT GUILTY) as charged in Count Eighteen of the Indictment.”
      Count Eighteen of the Indictment charged Rivera-Ruperto with "knowingly possess[ing] a firearm in furtherance of a drug trafficking crime as defined in Title 18, United States Code, Section 924(c)(2),” but made no mention of prior convictions under 18 U.S.C. § 924.

      . Jury instruction challenges generally must be preserved at trial, but a defendant may preserve his challenge to an instructional Ap-prendi/AlIeyne error by objecting at sentencing. See United States v. Pizarro, 772 F.3d 284, 296 (1st Cir. 2014). The government also concedes that our review here is de novo.

      . Rivera-Ruperto did raise his sentencing manipulation argument during his first sentencing hearing before the first district judge, and it would therefore be reasonable to treat the sentencing manipulation argument as altogether waived as to his second sentence. The government, however, does not argue waiver in its brief. Thus, favorably to Rivera-Ruperto, we review for plain error.

      . Rullán-Santiago was one of the co-defendants in this case below, but is not a party to this appeal.

      . Rullán-Santiago took a plea deal, and was eventually sentenced to 19-years’ imprisonment.

      . It appears Méndez-Pérez may not have attempted to recruit Salinas-Acevedo. The video recording from the March 24 drug deal shows Camacho asking Salinas-Acevedo if he knows anyone "trustworthy” that he would recommend for future deals, to which Salinas-Acevedo suggests his "buddy” Méndez-Pérez, and then appears surprised to hear that Méndez-Pérez was "already part of the clan." The government argues that if Méndez-Pérez had actually induced Salinas-Acevedo into participating in the March 24 drug deal, Salinas-Acevedo would not have been surprised to hear he was already in on the conspiracy. Salinas-Acevedo does not challenge this argument.

      . Salinas-Acevedo appears to raise an alternative argument in his reply brief that he was not required to meet this third factor at all, and that the factors laid out in Luisi, 482 F.3d at 55, are merely factors for the district court to weigh in assessing a defendant's derivative entrapment theory. We need not address an argument raised for the first time in a party’s reply brief. See N. Am. Specialty Ins. Co. v. Lapalme, 258 F.3d 35, 45 (1st Cir. 2001) (“[A]bsent exceptional circumstances, an appellant cannot raise an argument for the first time in a reply brief.”). Nor would it make any difference here because Salinas-Acevedo is incorrect. All five Luisi factors must be met in order to warrant an entrapment instruction based on the conduct of a middleman. See Luisi, 482 F.3d at 55; see also United States v. Navedo-Ramirez, 781 F.3d 563, 570 n.1 (1st Cir. 2015) (describing the Luisi factors as “conditions” that must be "satisfied”).

      . We do not consider Salinas-Acevedo’s originally-proffered claim that Rullán-Santiago duped him into participating in the March 24 deal by misrepresenting it as a legitimate business transaction over the sale of diamonds. Salinas-Acevedo conceded below that he had no proof that it was Camacho who directed or in any way encouraged Rullán-Santiago to tell him this lie. See United States v. Gates, 709 F.3d 58, 63 (1st Cir. 2013) (“[A] party cannot concede an issue in the district court and later, on appeal, attempt to repudiate that concession and resurrect the issue. To hold otherwise would be to allow a litigant to lead a trial court down a primrose path and later, on appeal, profit from the invited error.”). Because Salinas-Acevedo has no evidence connecting the puiported misrepresentation to a government agent, it does not factor into our derivative entrapment analysis.
      Although Salinas-Acevedo was not permitted to argue that he was lied to as part of an entrapment defense, we note that he did have an opportunity to do so at trial as part of his argument that he lacked the mens rea to commit the crime. The jury was thus presented evidence of the alleged misrepresentation—including the phone conversation in which Rullán-Santiago told Camacho that Salinas-Acevedo would "jump off the balcony” upon seeing the drugs—and had the opportunity to consider it in coming to its verdict.

      . Because the majority does not believe that the third prong is satisfied here, it does not reach the fourth and fifth ones. For the same reason, the majority also does not reach the improper inducement prong of the entrapment analysis. On the facts of this case, I have no difficulty finding that all these prongs have been met.

      . Another example of improper inducement is "dogged insistence until [defendant] capitulated”. Gendron, 18 F.3d at 961 (quoting United States v. Rodriguez, 858 F.2d 809, 815 (1st Cir. 1988) (alteration in original)); see also United States v. Montoya, 844 F.3d 63, 67 (1st Cir.2016) ("[Improper inducement] might include, for example, ... relentless insistence ... to participate in a criminal scheme”). In the present case, I have no difficulty finding that the government agent told the middleman to engage in "dogged insistence” or “relentless insistence.” This dissent focuses on "repeated suggestions” in light of defendant's difficult financial situation, because the facts of this case shout out "repeated suggestions” even more loudly than they do "dogged insistence” and “persistent insistence.”


author: LIPEZ, Circuit Judge.

text:
    UNITED STATES of America, Appellee, v. Joseph MARTINEZ-ARMESTICA, Defendant, Appellant.
    No. 14-1674
    United States Court of Appeals, First Circuit.
    January 20, 2017

      John E. Mudd, with whom Law Offices of John E. Mudd were on brief, for appellant.
    Susan Jorgensen, Assistant United States Attorney, with whom Rosa Emilia Rodríguez-Vélez, United States Attorney, and Nelson Jose Pérez-Sosa, Assistant United States Attorney, Chief, Appellate Division, were on brief, for appellee.
    Before LYNCH, SELYA, and LIPEZ, Circuit Judges.
   LIPEZ, Circuit Judge.

Joseph Martinez-Armestiea (“Martinez”) was charged with two counts of carjacking, one count of using, carrying, and brandishing a firearm during a crime of violence, and four counts of illegal possession of firearms seen in photographs on Martinez’s cell phone. He pled guilty to the carjacking counts and not guilty to the others. After a three-day jury trial, Martinez was convicted on all five remaining counts and sentenced to 180 months in prison. He appeals his convictions and sentence, arguing that there was insufficient evidence for the jury to find that he brandished a real gun during the carjacking, that the trial judge erred in admitting testimony from the government’s firearms expert related to the illegal possession counts, and that his sentence was unreasonable. Following a careful review of his claims, we affirm.

I.

Because Martinez challenges the sufficiency of the evidence against him on the brandishing count, we state the facts in the light most favorable to the jury’s verdict. United States v. Cruz-Rodriguez, 541 F.3d 19,25 (1st Cir. 2008).

On September 25, 2012, at approximately 10:15 p.m., Zuleyka Arroyo-Melendez (“Arroyo”) drove her 22-year-old niece, Stephanie Ramirez, to the Martinez Nadal train station in Puerto Rico. Ramirez had left her own SUV in the train station parking lot earlier in the day and had asked her aunt to drive her there after work so she could pick it up. Arroyo parked next to her niece’s SUV, and Ramirez switched cars. Ramirez had turned her car on and was preparing to back out of her parking space when a white Toyota pulled up in the parking lot behind the two women. Two men, aged between 19 and 23 years old, also appeared behind them. One of the men, later identified as Martinez, approached Ramirez’s SUV holding what the women described as a small, black pistol. He yelled at Ramirez to get out of her car and held the pistol to her head. Ramirez complied. Martinez got into Ramirez’s SUV and, after heeding her pleas to throw her bag of college books to her, drove away.

Meanwhile, the second man approached Arroyo and stood approximately two feet away from her, pointing at her what was described as a second black pistol. After Martinez left, the second man got into Arroyo’s SUV but, finding himself unable to turn off the emergency brake, called Arroyo over to the car. Pushing the muzzle of his pistol against her abdomen, he demanded that she lower the emergency brake handle. Arroyo later described the pistol as feeling hard and “a bit cold.” She complied, but pleaded with him not to take the car and leave her stranded in the parking lot with her niece. He responded by saying that he needed the car, but he agreed to give Arroyo her house keys. He then drove away in Arroyo’s SUV.

Arroyo later recognized Martinez and his accomplice in a photo she saw posted on Facebook and identified the two men to the police. When Martinez was taken into custody the police seized a cell phone from him, which was later found to contain at least four photos of Martinez with guns.

In July 2013, a grand jury returned a superseding indictment charging Martinez with two counts of carjacking and one count of brandishing a firearm during and in relation to a crime of violence. Martinez was also indicted on four counts of unlawful possession of a firearm by a convicted felon based on the photos discovered on his phone. As noted, he pled guilty to the two counts of carjacking but elected to go to trial on the other five counts. He was found guilty on all counts.

Martinez was subsequently sentenced to 71 months for each of the carjacking and illegal possession offenses, to be served concurrently. The district court also imposed a consecutive sentence of 109 months for brandishing a firearm during a crime of violence, which included a 25-month variance over the Guidelines-recommended sentence. This appeal followed.

II.

A. Sufficiency of the Evidence for Brandishing a Firearm During a Crime of Violence

Martinez argues that the evidence presented at trial was insufficient for the jury to find that he brandished a firearm during the carjacking. A conviction under 18 U.S.C. § 924(c) requires proof that the defendant wielded a “firearm,” which is defined as

(A) any weapon (including a starter gun) which will or is designed to or may readily be converted to expel a projectile by the action of an explosive; (B) the frame or receiver of any such weapon; (C) any firearm muffler or firearm silencer; or (D) any destructive device. Such term does not include an antique firearm.

18 U.S.C. § 921(a)(3). The firearm must be “real,” rather than a toy or replica, but it “need not be prove[d] to be loaded or operable.” United States v. Taylor, 54 F.3d 967, 975 (1st Cir. 1995) (quoting United States v. Kirvan, 997 F.2d 963, 966 (1st Cir. 1993)).

Martinez contends that the government failed to establish that the object in his hand was a real gun. Sufficiency of the evidence claims are reviewed de novo when, as here, they have been preserved for appeal. United States v. De León-Quiñones, 588 F.3d 748, 751 (1st Cir. 2009). We give deference to the jury’s determination, however, viewing the evidence in the light most favorable to the government and asking “whether any rational trier of fact could have found the essential elements of the crime beyond a reasonable doubt.” United States v. Roberson, 459 F.3d 39, 47 (1st Cir. 2006) (quoting United States v. Bailey, 405 F.3d 102, 111 (1st Cir. 2005)).

At trial, both Arroyo and Ramirez testified about Martinez’s use of a gun during the carjacking. Martinez argues that because neither woman actually stated that the gun was real, their testimony about the gun was not specific enough to support a jury finding to that effect. He also attempts to cast doubt on their ability to adequately see the object in his hand, asserting that the parking lot was not well lit and that Ramirez could see only part of the gun.

Martinez’s attempt to discredit the evidence before the jury is unavailing. Both women described the object as a “black pistol.” Arroyo also testified that she knew the difference between a pistol and a revolver, permitting the jury to infer that she had some familiarity with firearms. Neither woman referred to the gun in Martinez’s hand in any way that would indicate that it was not real. See United States v. Cruz-Diaz, 550 F.3d 169, 173 (1st Cir. 2008) (finding that the totality of evidence, including the lack of an indication in the witness testimony that the “pistol” described by the witnesses was fake, supported an inference by the jury that the defendant used a real gun). Moreover, the two witnesses’ reactions to the gun provide further circumstantial evidence that they believed it to be real: both women gave up their cars and keys in response to the threats of Martinez and his accomplice, and Arroyo testified that she thought Martinez was-going to kill her niece. See De León-Quiñones, 588 F.3d at 752 (finding sufficient evidence for a § 924(c) conviction based, in part, upon evidence of the victims’ reaction indicating that they believed the defendant’s gun was real).

Nor is there any reason to doubt the witnesses’ testimony that they could see the gun. Both Arroyo and Ramirez pointed out that the parking lot was lit, and Arroyo noted that she had parked her SUV directly next to a lamp post. Ramirez also testified that she could see clearly during the episode. Moreover, Arroyo, who observed the gun from only 2 to 3 feet away while Martinez pointed it at her niece, testified that she was paying close attention because “I thought he was going to kill her.”

Martinez also attempts a more general challenge to Arroyo and Ramirez’s testimony, arguing that the testimony of a lay witness who lacks experience with guns is categorically insufficient to prove that an object is a real gun. Instead, he argues, the testimony of an expert witness is required, or, as in Roberson, at least the testimony of a witness who handled the object at issue and has some familiarity with firearms. See 459 F.3d at 47. Along with other circuits, we have squarely rejected the argument that such expert testimony is necessary. See Taylor, 54 F.3d at 975 (“lay opinion testimony may be employed to propel a finding that an object is in fact a real gun”); see also, e.g., United States v. Lawson, 810 F.3d 1032, 1040 (7th Cir. 2016); United States v. Stenger, 605 F.3d 492, 504 (8th Cir. 2010). Furthermore, a witness need not be familiar with firearms, nor have held the weapon to testify that it was real. See United States v. Jones, 16 F.3d 487, 490-91 (2d Cir. 1994) (finding testimony of eyewitnesses who were “not familiar with weapons” sufficient to sustain conviction under § 924(c)); Parker v. United States, 801 F.2d 1382, 1383-85 (D.C. Cir. 1986) (rejecting the contention that eyewitness testimony will not suffice to establish that an object is a gun unless “it [was] given by persons knowledgeable about firearms who had an opportunity to examine the weapon closely”).

Martinez argues that these precedents should be reevaluated in light of the 2000 amendments to Rule 701 of the Federal Rules of Evidence, which he claims were intended to “mak[e] it much more difficult for laypersons to testify as to issues better left for experts.” That argument, which was limited to one sentence of appellant’s brief, was raised in such a perfunctory manner that we deem it waived. See United States v. Zannino, 895 F.2d 1, 17 (1st Cir. 1990) (“[I]ssues adverted to in a perfunctory manner, unaccompanied by some effort at developed argumentation, are deemed waived.... ‘[A] litigant has an obligation “to spell out its arguments squarely and distinctly,” or else forever hold its peace.’ ” (quoting Rivera-Gomez v. de Castro, 843 F.2d 631, 635 (1st Cir. 1988))). Even so, this circuit’s post-2000 decisions clearly reaffirm that the testimony of a person with specialized knowledge is not required to sustain a jury finding that a gun was real. See, e.g,, Cruz-Diaz, 550 F.3d at 173 (affirming conviction based on the testimony of four bank employees, none of whom held the gun or had specialized expertise); De León-Quiñones, 588 F.3d at 752 (affirming conviction based on the testimony of three bank employees, none of whom held the gun or had specialized expertise).

We therefore reject Martinez’s contention that the evidence was insufficient to support his conviction for brandishing a firearm during a crime of violence.

B. Admission of Expert Testimony

At trial the government called Agent Douglas J. Halepaska, Jr., a firearms and tool marks examiner for the laboratory division of the Federal Bureau of Investigation (“FBI”), to testify in support of the charges of illegal possession of a firearm. Halepaska analyzed photos found on Martinez’s phone showing Martinez in possession of guns, which served as the basis for the illegal possession charges.

The government presented Halepaska’s conclusions as expert testimony. Pursuant to Federal Rule of Evidence 702, Halepas-ka first testified about his qualifications and methods. He described in detail the “lengthy and extensive training program” he had undergone at the FBI before being certified as a firearms and tool mark examiner. He then explained the various kinds of forensic analyses he performs on firearms evidence. For photographs such as those on Martinez’s phone, he performs an “association examination,” or more specifically a “photograph analysis,” in which he examines specific physical characteristics of the gun in a photo and determines which manufacturers and models of guns are consistent with those features. After making an initial assessment, he obtains firearms from the FBI’s collection of over 7,000 reference firearms to compare directly with the photos. He then creates an illustration that mimics the photo by placing the reference firearm in a similar position to that of the unknown gun. This positioning allows him to make a direct comparison of features so that he can narrow the subset of potential firearms that are consistent with the pictured gun.

Upon questioning by defense counsel, Halepaska admitted that his examination in this case was only the third association analysis he had conducted since being certified, and that this was the first time he had testified in court about an association examination. At that point defense counsel objected to his qualification as an expert. The judge overruled the objection and declared Halepaska an expert in determining whether an object in a photograph is consistent with a specific brand or model of gun.

Halepaska then testified that he had conducted a “photograph analysis” of three of the photos found on Martinez’s phone, each of which featured Martinez with an object that appeared to be a gun. Hale-paska concluded that the item in each of the three photos was consistent with a pistol manufactured by Glock. On cross examination, however, he admitted that he could not determine whether the guns in the photos were functional firearms, replica firearms, or toy firearms. He explained that, in order to determine whether a gun was real, he would need to examine it in person.

Martinez claims that Halepaska’s testimony failed to meet the requirements of Federal Rule of Evidence 702. That rule “imposes a gate-keeping role on the trial judge to ensure that an expert’s testimony ‘both rests on a reliable foundation and is relevant to the task at hand.’” United States v. Vargas, 471 F.3d 255, 261 (1st Cir. 2006) (quoting Daubert v. Merrell Dow Pharms., Inc., 509 U.S. 579, 597, 113 S.Ct. 2786, 125 L.Ed.2d 469 (1993)). It states:

A witness who is qualified as an expert by knowledge, skill, experience, training, or education may testify in the form of an opinion or otherwise if:
(a) the expert’s scientific, technical, or other specialized knowledge will help the trier of fact to understand the evidence or to determine a fact in issue;
(b) the testimony is based on sufficient facts or data;
(c) the testimony is the product of reliable principles and methods; and
(d) the expert has reliably applied the principles and methods to the facts of the case.

Fed. R. Evid. 702.

Appellant argues that the district court abused its discretion by admitting Hale-paska’s testimony, alleging defects relating to all but the last of the rule’s requirements. He contends that Halepaska was unqualified to offer expert testimony to the jury because he had not been trained to distinguish replica and toy guns from real guns, that Halepaska’s testimony was not helpful to the jury, that it was not based on sufficient data, and that the government did not establish that Halepaska had used reliable principles and methods to reach his conclusions.

Although Martinez objected generally to Halepaska’s qualification as an expert witness at trial, none of these specific critiques of Halepaska’s qualifications as an expert was raised before the district court. Consequently, none of these arguments was preserved for appeal, suggesting the applicability of plain error review. See United States v. Mercado, 412 F.3d 243, 247 (1st Cir. 2005) (“It is well established that an objection on one ground does not preserve appellate review of a different ground.” (quoting Negron v. Caleb Brett U.S.A., Inc., 212 F.3d 666, 672 (1st Cir. 2000))); United States v. Diaz, 300 F.3d 66, 75-76 (1st Cir. 2002) (applying plain error review after concluding that an objection to an expert’s qualifications was insufficient to preserve a challenge to the reliability of the expert’s methods),

Oddly, the government ignores the plain error issue and asserts that the trial judge’s ruling should be reviewed for abuse of discretion. See Gen. Elec. Co. v. Joiner, 522 U.S. 136, 141, 118 S.Ct. 512, 139 L.Ed.2d 508 (1997) (stating that a district court’s decision to admit or exclude expert testimony is generally reviewed under an abuse of discretion standard). Because of the government’s failure to request plain error review, we will apply the standard of review applicable to a properly preserved claim. United States v. Paulino-Guzman, 807 F.3d 447, 450 n.5 (1st Cir. 2015) (“ ‘[w]hen the government fails to request plain error review,’ we may ‘review the claim under the standard of review that is applied when the issue is properly preserved below.’ ” (alteration in original) (quoting United States v. Encarnación-Ruiz, 787 F.3d 581, 586 (1st Cir. 2015))). Accordingly, we review the district court’s decision to admit Halepaska’s testimony for abuse of discretion, keeping in mind that trial judges are afforded “substantial latitude in the admission or exclusion of opinion evidence.” First Marblehead Corp. v. House, 541 F.3d 36, 40 (1st Cir. 2008) (quoting Crowe v. Marchand, 506 F.3d 13, 16 (1st Cir. 2007)).

Turning to Martinez’s arguments, we note that two of them miss the mark because they are based on the same false premise. First, Martinez argues that Hale-paska was unqualified to offer expert testimony to the jury because he had not been trained to distinguish replica and toy guns from real guns. Second, he asserts that Halepaska did not have a sufficient factual basis to determine whether the guns in the photos were real or replicas because he was unable to examine the actual firearms pictured in the photos. Both arguments are based on the incorrect assertion that Halepaska offered testimony that the guns in the photos were real.

Instead, Halepaska’s testimony was limited to opining on the consistency of features he observed on the pictured guns with features of Glock-manufactured pistols, Indeed, Halepaska himself stated that he would need to physically examine the gun to determine whether it was real, a replica, or a toy. Recognizing that he lacked such a factual basis, Halepaska declined to offer any opinion on whether the pictured guns were real. Moreover, the district judge’s qualification of Halepaska as an expert was limited in scope to the comparison of features of the pictured and reference guns. Specifically, the judge stated: “I believe that from preliminary questions submitted by counsel to Mr. Ha-lepaska, that he is qualified as an expert to testify concerning the association between an object on a photograph and a real pistol and the association as to the characteristics, if they are consistent with the other.”

Martinez also argues that Halepaska failed to offer technical or specialized knowledge that would assist the jury in determining a fact in issue and, hence, his testimony was not relevant. See Ruiz-Troche v. Pepsi Cola of P.R. Bottling Co., 161 F.3d 77, 81 (1st Cir. 1998) (“To be admissible, expert testimony must be relevant not only in the sense that all evidence must be relevant, but also in the incremental sense that the expert’s proposed opinion, if admitted, likely would assist the trier of fact to understand or determine a fact in issue.” (citations omitted)). Martinez insists that the jurors could have done what Halepaska did—compare the photos to real firearms—and reached the same conclusions. This argument misconstrues the way in which Halepaska’s testimony was helpful to the jury.

Halepaska did not simply compare the photographs to real firearms. Instead, he first had to determine which, if any, of the 7,000 guns in the FBI’s reference firearms collection had features consistent with the items in the photos. This analysis required knowledge of the characteristics of thousands of guns, as well as the expertise to know which characteristics are relevant for distinguishing among different brands and models of guns. A lay person generally would not possess such knowledge. See United States v. Corey, 207 F.3d 84, 96 (1st Cir. 2000) (“[Tjestimony identifying the manufacturer of a firearm will usually constitute technical or specialized knowledge that will assist the trier of fact.”). His testimony that the guns in the photographs were consistent with Glock pistols, then, was not based simply upon the comparison of guns in photographs with a real gun, but also upon expertise which allowed him to determine the most apt comparator gun.

Martinez also faults the government for failing to elicit explicit testimony from Ha-lepaska about the reliability of his methods. Two features of Halepaska’s analysis provide a fair proxy for such explicit testimony, however. Halepaska’s analysis consisted of two steps: first, using his specialized knowledge to pick out the most apt comparator gun, and second, assessing the consistency of the pictured gun with the comparator gun. As explained below, the reliability of the former process is supported by Halepaska’s extensive training, and the reliability of the latter process is supported by the simplicity of that task.

The first step of Halepaska’s analysis required him to use his specialized knowledge of the features of various brands and models of firearms to choose a gun that was similar to one featured in a photo. The accuracy of this determination depended largely on the quality of the specialized knowledge he applied to the task. Consequently, the reliability of this step could be ascertained by examining the strength of the background from which he derived his expertise. Often in fields based upon specialized knowledge rather than scientific expertise, the “expert’s experience and training bear a strong correlation to the reliability of the expert’s testimony.” United States v. Jones, 107 F.3d 1147, 1155 (6th Cir. 1997). Indeed, the Advisory Committee on the 2000 amendments to the Federal Rules of Evidence noted that “[i]n certain fields, experience is the predominant, if not sole, basis for a great deal of reliable expert testimony.” Fed. R. Evid. 702 advisory committee’s note to 2000 amendments.

Halepaska’s training and experience support the reliability of his testimony. Before the district court qualified Halepas-ka as an expert witness, the agent testified in detail about his training and experience with firearms. He stated that he had undergone “a lengthy and extensive training program” during his four years working in the FBI’s laboratory division. That preparation included touring firearms manufacturing facilities, reading articles and books about “the discipline of firearms and tool marks examinations,” and hands-on instruction. In this on-the-job training, under the “direct supervision of a qualified and experienced firearms and tool mark examiner,” he worked with sample weapons, on which he conducted “hundreds of examinations, thousands of observations.” At the end of this training, he passed oral and written examinations to become certified as a firearms and tool mark examiner. He examined at least one hundred firearms for the FBI after completing his training. Moreover, even before beginning his training with the FBI, he had gained experience with firearms by serving as an infantryman in the Marine Corps for five years. In short, his experience with firearms was both considerable and wide-ranging. This specialized knowledge formed the basis for the first step of the “association examination” upon which Ha-lepaska based his expert opinion.

The second step of Halepaska’s analysis required him to determine whether the features of the chosen reference gun were consistent with those of the pictured gun. In essence, this was a simple task, requiring a visual comparison of two photographs, one of the chosen reference gun, the other of the pictured gun. Because of this simplicity, the district court did not have to consider technical data, such as the method’s error rate or whether it had been subjected to peer review, in order to make its reliability determination. See Kumho Tire Co. v. Carmichael, 526 U.S. 137, 150-52, 119 S.Ct. 1167, 143 L.Ed.2d 238 (1999) (“[T]he factors identified in Daubert may or may not be pertinent to assessing reliability, depending on the nature of the issue, the expert’s particular expertise, and the subject of his testimony.... Otherwise, the trial judge would lack the discretionary authority needed ... to avoid unnecessary ‘reliability’ proceedings in ordinary cases where the reliability of an expert’s methods is properly taken for granted.... ” (internal quotation omitted)). Instead, the district court could reasonably have determined, based upon an explanation of Halepaska’s technique, that his visual comparison of objects was a reliable method of determining the consistency of their physical features.

Taken together, Halepaska’s extensive experience and the simplicity of his technique establish a fair proxy for explicit testimony about the reliability of his methods. The district court did not abuse its discretion by qualifying Halepaska as an expert witness.

C. Reasonableness of the Sentence

Martinez challenges the substantive reasonableness of his sentence, targeting the upward variance applied by the district court when sentencing him for brandishing a firearm during the commission of a crime of violence. See 18 U.S.C. § 924(c)(l)(A)(ii) and (3). Claiming that the court based the increase on a consideration already factored into the Guidelines-recommended sentence—i.e. his use of weapons—Martinez argues that it was unreasonable for the sentencing judge to rely on such a factor. The government responds that there was no abuse of discretion in the district court’s choice of sentence. See Gall v. United States, 552 U.S. 38, 41, 128 5.Ct. 586, 169 L.Ed.2d 445 (2007) (holding that substantive reasonableness is generally reviewed under the abuse of discretion standard).

The district court found that, taken together, the two carjacking charges and four illegal possession charges produced a Guidelines sentencing range (“GSR”) of 57-71 months. Martinez does not challenge that calculation. The court also noted that the Guidelines sentence for the charge of brandishing a firearm during a crime of violence is the minimum term of imprisonment required by the statute, or 84 months. See U.S.S.G. § 2K2.4(b). Defense counsel acknowledged that this term was to be served consecutively with the sentence for the other charges, yielding an overall sentencing range of 141 to 155 months.

Before announcing the sentence, the district court addressed the factors set forth in 18 U.S.C. § 3553(a), noting the particularly violent and dangerous manner in which Martinez committed the carjacking and brandishing crimes here as well as a prior crime which had also involved a firearm. Based on those factors, the district court concluded that Martinez was “prone to using firearms” and that he was “possibly [a] very dangerous person to the community.” It sentenced Martinez to 71-month terms of imprisonment for each of the carjacking and illegal possession offenses, to be served concurrently, and imposed a consecutive term of 109 months for brandishing a firearm during a crime of violence, a variance of 25 months over the 84-month Guideline sentence.

Appellant relies on United States v. Of-ray-Campos in asserting that the variance constitutes an abuse of discretion because the district court considered a factor that was already accounted for in the Guidelines-recommended sentence, specifically his use of weapons. See 534 F.3d 1, 43 (1st Cir. 2008). Because he was convicted of offenses based on his possession and brandishing of guns, he argues, the district court could not base an upward departure on those same incidents of weapon usage.

We did not hold in Ofray-Campos, however, that the consideration of such factors was unreasonable. Instead, we stated that when imposing a variance based on factors that overlap with considerations included in the Guidelines sentence, the district court “must articulate specifically the reasons that this particular defendant’s situation is different from the ordinary situation covered by the [Guidelines calculation.” Id. (quoting United States v. Zapete-Garcia, 447 F.3d 57, 60 (1st Cir. 2006)).

In this case, the district court articulated several factors demonstrating that Martinez’s conduct went beyond the ordinary conduct proscribed by the statute. It pointed to Martinez’s repeated, threatening use of firearms in finding that he was “prone to using firearms” and “possibly very dangerous ... to the community.” Rather than simply brandishing a weapon, Martinez pointed the gun directly at one of the carjacking victims, holding it against her head. Moreover, he brandished the gun in the parking lot of a public train station.

The district court also considered factors related to Martinez’s criminal history and personal characteristics. Martinez had previously been convicted for violation of a Puerto Rico weapons law. That conviction was based upon a prior armed robbery, during which he had aimed a firearm at a victim. He had also shot the gun into the air twice, once again in a public place. Combined with Martinez’s continued possession of firearms, as demonstrated by the photos found on his phone, the district court could reasonably attribute to Martinez an ongoing and unremitting proclivity toward the use and possession of dangerous weapons. This substantial history of firearms abuse supports the district court’s decision to exceed the Guidelines sentence that would apply to a first time offender who had committed the minimum offense conduct.

Martinez also argues that the size of the variance renders his sentence unreasonable. Here, the 180-month sentence imposed by the district court constitutes a 16% increase over the high end of the Guidelines range. As an initial matter, the Supreme Court .has rejected “the use of a rigid mathematical formula that uses the percentage of a departure as the standard for determining the strength of the justifications required for a specific sentence.” Gall, 552 U.S. at 47, 128 S.Ct. 586. Where the sentence is outside the Guidelines term, we “may consider the extent of the deviation, but must give due deference to the district court’s decision that the § 3553(a) factors, on a whole, justify the extent of the variance.” Id. at 51,128 S.Ct. 586.

The roughly two-year variance in Martinez’s sentence is “modest,” and “not unreasonable in light of the totality of the circumstances” surrounding Martinez’s repeated use of firearms in a manner dangerous to the public. See United States v. Guzman-Fernandez, 824 F.3d 173, 178 (1st Cir. 2016). Indeed, the 84-month Guidelines sentence is the statutory minimum, reflecting Congress’s expectation that it is merely the starting point for determining the appropriate term of imprisonment for a defendant convicted of violating § 924(c)(l)(A)(ii). The district court’s upward variance must be viewed in the context of the entire statutory sentencing range, which begins at 84 months and has an upper bound of life imprisonment.

We thus reject Martinez’s contention that his sentence was unreasonable.

Affirmed.

      . Martinez also submitted a pro se letter, purportedly pursuant to Federal Rule of Appellate Procedure 28(j), arguing, based upon Johnson v. United States, — U.S.—, 135 S.Ct. 2551, 192 L.Ed.2d 569 (2015) and Welch v. United States, — U.S. —, 136 S.Ct. 1257, 194 L.Ed.2d 387 (2016), that his carjacking conviction is not a crime of violence under 18 U.S.C. § 924(c)(3). Because this is a new argument, rather than a citation of supplemental authorities, it is not properly raised through a Rule 280 letter. Moreover, Welch did not answer any question currently applicable to this case, and Johnson had already been decided when appellant submitted his opening brief. Consequently, Martinez has waived this argument by not raising it in a timely manner. See Young v. Wells Fargo Bank, N.A., 828 F.3d 26, 32 (1st Cir. 2016).

      . As explained in greater detail by Agent Douglas J. Halepaska, Jr., a firearms and tool marks examiner called at trial as a witness by the government, both pistols and revolvers are handguns. A revolver has a cylinder containing a number of separate chambers that rotate around a central axis. When a unit of ammunition is discharged, it moves from one of those chambers into the barrel of the gun. In a pistol, by contrast, the chamber and the barrel are integrated as one unit.

      . Halepaska’s analysis addressed only the photos dated June 17, 2012, June 22, 2012 and August 26, 2012. The fourth photo, dated September 24, 2012, was not provided to him and he did not testify about its contents.

      . Given the context of Halepaska's testimony, we take "real pistol” to refer to Halepaska’s use of reference firearms in his analysis rather than his ability to determine whether a gun in a photo is real.

      . In arguing that the expert testimony was improperly admitted, appellant also suggests that the evidence presented in support of the illegal possession charges was insufficient to support the verdict. In doing so, however, he incorrectly describes what took place at trial, asserting that “simply showing firearms to the jury to compare with photographs would not be sufficient to find a violation of §§ 922 and 924.” Because the jury was not provided with firearms to compare with the photographs, the question of the sufficiency of that kind of evidence is not before us in this case. Beyond this erroneous characterization of the trial evidence, appellant's sufficiency argument is so undeveloped that it is inadequate to raise such a claim on appeal. See ■Zannino, 895 F.2d at 17. In fact, the government does not even address the sufficiency of the evidence in its brief. This lack of response does not control our determination that the issue was inadequately raised; we simply note it as further evidence of the inadequacy of appellant's briefing. The sufficiency of the evidence claim was preserved below by trial counsel, thereby permitting a developed argument if one had been made.

      . Citing a statement made by trial counsel at the sentencing, appellant’s brief states that the Guidelines range is 135 to 147 months. Appellant does not provide any support for this assertion, however; nor does he argue that the district court’s calculation of the Guidelines range is incorrect. We do not, therefore, take this to be an attempt to dispute the district court’s calculation of the GSR.

      . Appellant suggests that the variance constitutes a 22.4% increase over the upper end of the Guidelines range. As noted above, he bases his argument on an incorrect Guidelines range referenced by trial counsel during the sentencing.