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United States v. Rivera-Ruperto

United States Court of Appeals, First Circuit

January 13, 2017

WENDELL RIVERA-RUPERTO, a/k/a Arsenio Rivera, Defendant, Appellee.


          H. Manuel Hernández for appellant.

          Robert J. Heberle, Attorney, Public Integrity Section, Criminal Division, U.S. Department of Justice, with whom Francisco A. Besosa-Martínez, Assistant United States Attorney, Nelson Pérez-Sosa, Assistant United States Attorney, Chief, Appellate Division, and Rosa Emilia Rodríguez-Vélez, United States Attorney, were on brief, for appellee.

          Before Torruella, Lipez, and Thompson, Circuit Judges.

          THOMPSON, Circuit Judge.

         This case arises out of a now-familiar, large-scale FBI investigation known as "Operation Guard Shack, " in which the FBI, in an effort to root out police corruption throughout Puerto Rico, orchestrated a series of staged drug deals over the course of several years.[1] For his participation in six of these Operation Guard Shack drug deals, Defendant-Appellant Wendell Rivera-Ruperto stood two trials and was found guilty of various federal drug and firearms-related crimes. The convictions resulted in Rivera-Ruperto receiving a combined sentence of 161-years and 10-months' imprisonment.

         Although Rivera-Ruperto raises similar challenges in his appeals from the two separate trials, each trial was presided over by a different district judge. Thus, there are two cases on appeal, and we address the various challenges today in separate opinions.[2] In this present appeal from the first trial, Rivera-Ruperto argues that the district court committed reversible errors when it: (1) denied his claim for ineffective assistance of counsel during the plea-bargaining stage; (2) failed to instruct the jury that it was required to find drug quantity beyond a reasonable doubt; (3) either declined to consider or rejected his sentencing manipulation claim; and (4) sentenced him to a grossly disproportionate sentence in violation of the Eighth Amendment.

         For the reasons stated below, we affirm the district court.


         We keep our summary of the facts brief for now, saving the specific details related to Rivera-Ruperto's various challenges for our later discussion.

         Rivera-Ruperto provided armed security during six Operation Guard Shack sham drug deals, which occurred on April 9, April 14, April 27, June 9, June 25, and September 16 of 2010.[3]Each of the sham deals followed the same pattern. They involved undercover officers posing as sellers and buyers of fake cocaine, and took place at FBI-monitored apartments wired with hidden cameras. The April 9 and April 14 deals each involved 12 kilograms of fake cocaine, the April 27 and June 9 deals each involved 8 kilograms of fake cocaine, and the June 25 and September 16 deals each involved 15 kilograms of fake cocaine. On top of rendering armed security services, Rivera-Ruperto brought along with him additional recruits.[4] And at the April 27 deal, Rivera-Ruperto did even more; he sold a handgun, including magazines, to a confidential FBI informant posing as a drug dealer. For his services, Rivera-Ruperto received a payment of $2, 000 for each of the deals, except for the September 16 deal, for which he received $3, 000.

         The government charged Rivera-Ruperto under three separate indictments (two on September 21, 2010 and one on September 23, 2010) for his illegal participation in the six sham drug deals.[5] For each of the transactions, the indictments charged Rivera-Ruperto with one count each of conspiracy and attempt to possess with intent to distribute a controlled substance, as well as possession of a firearm in relation to a drug trafficking crime. Additionally, Rivera-Ruperto was charged with possessing a firearm with an obliterated serial number during the April 27 deal.

         Rivera-Ruperto's case proceeded to trial after plea negotiations with the government failed -- a point of contention that we get to shortly. For purposes of trial, the first September 21 indictment (which charged Rivera-Ruperto for the April 14, April 27, June 9, and June 25 deals) and the September 23 indictment (which charged him for the September 16 deal) were consolidated and tried together. A jury found Rivera-Ruperto guilty of all charges and the district judge sentenced him to 126-years and 10-months' imprisonment. It is this first trial which is the topic of the present appeal. As we discuss in more detail below, Rivera-Ruperto takes issue both with the judge's jury instructions and with the sentence he ultimately received.

         Over defense counsel's objections, the second September 21, 2010 indictment (which charged Rivera-Ruperto for his involvement in the transaction on April 9, 2010 only) was tried several months later before a different district judge. After a second jury found Rivera-Ruperto guilty on all counts, Rivera-Ruperto received a 35-year sentence of imprisonment.

         Rivera-Ruperto, who is presently serving his combined sentence of 161 years and 10 months, now timely appeals. Putting aside, as we are required to do, whatever misgivings we might have as to the need for or the wisdom in imposing a near two-life-term sentence to punish a crime that involved staged drug deals, sham drugs, and fake dealers, we turn to the task of assessing whether any of Rivera-Ruperto's legal arguments entitle him to relief. As we have already noted, we address only Rivera-Ruperto's challenges from his first trial, saving those from the second for discussion in our separate, related opinion.


         I. Lafler Motion

         Rivera-Ruperto first challenges the district court's denial of his claim that his first court-appointed attorney provided ineffective assistance at the plea-bargaining stage. We begin by recounting what happened below.

         A. Background

         About a month after Rivera-Ruperto was arraigned, the government made him an initial plea offer of 14 years that covered the charged offenses in all three indictments. Rivera-Ruperto's first court-appointed attorney, Jose Aguayo ("Aguayo"), successfully negotiated that offer down to 12 years. When Rivera-Ruperto refused to take the 12-year deal, Aguayo attempted to negotiate an even lower sentence, but the prosecution told Aguayo that its 12-year offer was final.

         Aguayo then showed Rivera-Ruperto the email, which spelled out the government's final offer of 12 years, and explained to him the repercussions of not taking the plea deal. But Rivera-Ruperto rejected the offer still, and directed Aguayo to make a counteroffer of 8 years instead. Unsurprisingly, the government refused the 8-year counteroffer.

         In a last-ditch effort, Aguayo joined defense attorneys for five other Operation Guard Shack defendants to attempt to negotiate a global plea deal for the six defendants as a group. The government responded to these overtures by renewing its 12-year offer for Rivera-Ruperto, but this time the offer had an expiration date. When Aguayo showed Rivera-Ruperto the renewed offer, Rivera-Ruperto, once again, rejected it. The offer lapsed on February 4, 2011. Accordingly, on February 7, 2011, the government filed an informative motion, in which it notified the court that plea negotiations had terminated and that a trial schedule needed to be set.

         On that same day, Aguayo, apparently alarmed by Rivera-Ruperto's behavior during their meetings regarding the plea negotiations, filed a request for a psychiatric exam for Rivera-Ruperto. In the motion, Aguayo stated that during their meetings, he had witnessed Rivera-Ruperto "exhibiting strange behavior which has progressively worsened, " and that Rivera-Ruperto "refuses to, or lacks the ability to appreciate the seriousness of his case, refuses to review the discovery material, appears to lose his lucidity, rants and raves, and vehemently argues with imaginary people in the attorney-client visiting room." The district court granted the motion by electronic order.

         Shortly after being examined in early June 2011, Rivera-Ruperto sent Aguayo an email, in which he stated that he wanted to take the (by then, already expired) 12-year plea offer. Aguayo responded by advising Rivera-Ruperto that the 12-year deal had timed out, and that they should await the results of the mental evaluation before resuming further plea negotiations. If he were to withdraw the request for the psychiatric examination before they saw the results, Aguayo explained, Rivera-Ruperto could later argue, even after accepting an offer, that he had not been mentally competent to accept it after all.

         When the results of the psychological exam came back in late June, the report deemed Rivera-Ruperto "stable" and contained no diagnoses for mental disorders that would affect Rivera-Ruperto's competency to stand trial.[6] As promised, Aguayo then reached out to the government to attempt to reopen plea negotiations. At first, it appeared the government would be unwilling to engage in further plea bargaining with Rivera-Ruperto, whom the government believed had shown himself to be a "malingerer." But Aguayo was insistent that it was not Rivera-Ruperto who had requested the psychological exam as a delay tactic, but Aguayo himself who had requested it, compelled by his duty to provide Rivera-Ruperto with effective assistance of counsel. After some back and forth, the government relented and agreed to entertain one, and only one more counteroffer from Rivera-Ruperto, but it warned that the counteroffer had to be "substantial" (specifically, somewhere in the ballpark of 20-23 years).

         Aguayo met with Rivera-Ruperto to relay this information, making clear that this was their last chance to make a counteroffer, and that a proposal of less than 20 years would not be considered. Despite this advice, Rivera-Ruperto insisted that Aguayo make a counteroffer of only 13 years. Unsurprisingly, the government again rejected this lowball, but nevertheless made one final offer of 18 years. Rivera-Ruperto said no, and then proceeded to fire Aguayo. With plea negotiations over (this time for good), the case was slated for trial.

         On March 23, 2012, nine months after the date of the psychological evaluation report and three days before trial was to begin, Rivera-Ruperto, through his second court-appointed attorney, filed a motion alleging that Aguayo had provided ineffective assistance of counsel at the plea-bargaining stage and asking the district court to order the government to reoffer the 12-year deal. The district court granted Rivera-Ruperto's request for an evidentiary hearing on the issue and, after hearing testimony from both Rivera-Ruperto and Aguayo and considering the documentary evidence, [7] the district court concluded there was no merit to the ineffective assistance of counsel claim, and denied Rivera-Ruperto's motion. Rivera-Ruperto says this was error.

         B. Analysis

         We review a district court's determination of ineffective assistance of counsel claims de novo and any findings of fact for clear error. Ortiz-Graulau v. United States, 756 F.3d 12, 17 (1st Cir. 2014).

         A defendant's Sixth Amendment right to competent counsel extends to the plea-bargaining process. Lafler v. Cooper, 132 S.Ct. 1376, 1380-81 (2012). A defendant claiming, as Rivera-Ruperto does here, that counsel's assistance was ineffective at the plea-bargaining stage, must meet the two-part test laid out in Strickland v. Washington, 466 U.S. 668, 687 (1984). Lafler, 132 S.Ct. at 1384. He must show, first, that counsel's performance was deficient, and second, that "the outcome of the plea process would have been different with competent advice." Id.

         Rivera-Ruperto argues that he meets both of these prongs. He contends that he "wanted to accept the 12-year plea offer, and would have sans his original defense counsel's decision to seek an unnecessary psychological evaluation, his related erroneous advice, and his refusal to inform the government and the district Court of [his] decision [to accept the 12-year offer]."[8]But this argument fails on both Strickland requirements. To start, Rivera-Ruperto has failed to establish that Aguayo's performance was defective.

         In order to meet the first Strickland prong, a defendant must show that "counsel's representation fell below an objective standard of reasonableness." Strickland, 466 U.S. at 688. Generally speaking, "counsel is strongly presumed to have rendered adequate assistance and made all significant decisions in the exercise of reasonable professional judgment." Id. at 690. Thus, in order to establish deficient performance, a defendant must show that, "given the facts known at the time, counsel's choice was so patently unreasonable that no competent attorney would have made it." Tevlin v. Spencer, 621 F.3d 59, 66 (1st Cir. 2010) (citing Knight v. Spencer, 447 F.3d 6, 15 (1st Cir. 2006)).

         Here, none of Aguayo's actions meets this standard. Aguayo sought a psychological exam only after he observed Rivera-Ruperto arguing with imaginary people and exhibiting other abnormal behavior. While ultimately the results of Rivera-Ruperto's exam may have shown that Rivera-Ruperto did not have any mental health issues, given the erratic behavior Rivera-Ruperto displayed during their meetings, Aguayo's motion was not "patently unreasonable." Tevlin, 621 F.3d at 66 (citation omitted).[9]

         Nor do we think Aguayo's performance was deficient on account of the fact that he advised Rivera-Ruperto to await the results of the psychological exam before pursuing further plea negotiations. First, as we get to in a moment, by the time Rivera-Ruperto had emailed Aguayo to say he wished to take the 12-year plea offer, there was no actual offer for Rivera-Ruperto to take because the last 12-year deal had expired some three or four months prior. But even if there had been a live offer on the table, by the time Rivera-Ruperto expressed any interest in taking a 12-year plea deal, he had already been examined and was awaiting the results. As Aguayo explained to Rivera-Ruperto at the time, it was Aguayo's professional judgment that withdrawing the motion for the psychological exam at that point would threaten the durability of any plea agreement they might have reached because Rivera-Ruperto could later argue that he had not been mentally competent to enter into the deal at all. We think this advice was given in the exercise of reasonable professional judgment, and in any event, certainly was not so deficient as to fall below "an objective standard of reasonableness." Strickland, 466 U.S. at 688. Rivera-Ruperto has therefore failed to show that Aguayo's performance was deficient.

         Moreover, even if we were to assume the defective performance prong has been met, Rivera-Ruperto's claim still fails because he cannot show the necessary prejudice to meet the second Strickland prong. In order to establish prejudice, a defendant claiming ineffective assistance at the plea bargaining stage must show that "but for the ineffective advice of counsel there is a reasonable probability that the plea offer would have been presented to the court[, ]. . . the court would have accepted its terms, and that the conviction or sentence, or both, under the offer's terms would have been less severe than under the judgment and sentence." Lafler, 132 S.Ct. at 1385. Rivera-Ruperto cannot do so here.

         Rivera-Ruperto argues that he would have accepted the 12-year deal but for Aguayo requesting an "unnecessary and unwanted" psychological exam and then refusing to withdraw the request after Rivera-Ruperto told Aguayo that he wished to accept the 12-year offer. But the facts simply do not bear out Rivera-Ruperto's theory that Aguayo's actions are what prevented a 12-year plea deal from being presented to the court. When Rivera-Ruperto emailed to tell Aguayo that he wanted to take the 12-year plea offer, it was already early June 2011. By that time, nearly four months had passed since the 12-year plea offer had expired. It was therefore not the requested psychological examination that caused Rivera-Ruperto to "lose" a 12-year plea deal, but the fact that he had already rejected the offer (more than once, we might add), leaving no deal on the table for Rivera-Ruperto to accept. Furthermore, even after the results came back from Rivera-Ruperto's psychological exam and the government had labeled him a "malingerer, " Rivera-Ruperto had a final opportunity to accept an 18-year plea offer from the government. Rivera-Ruperto rejected even this offer and opted for trial. Rivera-Ruperto has thus failed to show that there is a reasonable probability that any plea deal, much less the 12-year plea deal specifically, would have been presented to the court but for Aguayo's purported ineffective assistance.

         Because Rivera-Ruperto has failed to show that Aguayo's performance was defective, and because, even if we were to assume the performance was defective, Rivera-Ruperto has failed to show the requisite prejudice, we affirm the district court's ruling on the Lafler claim.

         II. Jury Instructions

         Rivera-Ruperto raises on appeal only one challenge concerning the trial itself. He argues that the district court erred in failing to instruct the jury that it was required to make its drug quantity findings beyond a reasonable doubt. We begin once more with a discussion of what happened below.

         A. Background

         After closing arguments were made, the trial judge gave jury instructions, beginning with general instructions, which explained that the prosecution had the burden "to prove guilt beyond a reasonable doubt." The trial judge then instructed the jury on the elements of the crimes with which Rivera-Ruperto was charged.

         As a reminder, among other charges, Rivera-Ruperto was indicted for each of the five drug deals with one count each of two drug crimes: conspiracy and attempted possession with intent to distribute a controlled substance. As they are the only instructions relevant to our inquiry today, we focus our attention on the judge's instructions regarding drug quantity.

         The judge instructed the jury as to the elements of the two drug offenses, and was explicit that in order to find the defendant guilty, the jury had to be convinced that the government had proven each element beyond a reasonable doubt. The judge did not include drug quantity among these elements, but after explaining the elements of the drug crimes, the judge did tell the jury: "If you find that the defendant conspired or attempted to possess with intent to distribute a controlled substance[, ] . . . you will be asked to also make findings as to the quantity of this substance that the defendant either conspired or attempted to possess."

         The trial judge referred to drug quantity one other time in his jury instructions. This was when he described the verdict forms to the jury, explaining: "[I]f you find [the] [d]efendant guilty, then you are also asked to provide the amount of drugs involved in said count. And there's a question for you to find that."[10]

         Rivera-Ruperto's trial attorney raised no objections to the jury instructions. After deliberations, the jury returned a verdict in which it found Rivera-Ruperto guilty of all charges. With respect to the drug-related offenses, the jury found Rivera-Ruperto guilty "[i]n the amount of five kilograms or more" for each of the counts, with the exception of the attempted possession count for the September 16 deal, for which the jury did not return a drug quantity finding.[11]

         At sentencing, the district court imposed a sentence for these drug convictions that was based on the jury's drug quantity findings. Specifically, because the jury had found that all of Rivera-Ruperto's drug offenses (except the September 16 attempted possession count) involved 5 kilograms or more of a controlled substance, the court imposed concurrent sentences of 21-years and 10-months' imprisonment for each of these convictions.[12] The sentences thus exceeded the 20-year statutory maximum for offenses involving an indeterminate quantity of drugs, see 21 U.S.C. § 841(b)(1)(C), and instead fell within the minimum 10-year to maximum life sentencing range for offenses involving 5 kilograms or more of a controlled substance, id. § 841(b)(1)(A).

         On appeal, Rivera-Ruperto argues that he is entitled to a new trial because the district court failed to instruct the jury that it was required to find the drug quantities beyond a reasonable doubt.

         B. Analysis

         We typically review jury instruction challenges de novo, but where, as here, a defendant failed to object to the jury instructions below, our review is for plain error. United States v. Delgado-Marrero, 744 F.3d 167, 184 (1st Cir. 2014).

         Reversal under the plain error standard requires: (1) that an error occurred; (2) that the error was obvious; (3) that it affected the defendant's substantial rights; and (4)that it threatens the fairness, integrity or public reputation of the proceedings. Delgado-Marrero, 744 F.3d at 184. We have noted previously that "[t]his multi-factor analysis makes the road to success under the plain error standard rather steep; hence, reversal constitutes a remedy that is granted sparingly." United States v. Gelin, 712 F.3d 612, 620 (1st Cir. 2013).

         We begin with the question of error. To satisfy plain error review, we must conclude not only that the district court erred in not instructing the jury that it was required to find drug quantity beyond a reasonable doubt, but that the error was obvious.

         The Supreme Court has held that facts such as drug quantity are to be considered elements of the offense and must be found beyond a reasonable doubt if those facts "increase the penalty for a crime beyond the prescribed statutory maximum, " Apprendi v. New Jersey, 530 U.S. 466, 490 (2000), or increase the mandatory minimum sentence for a crime, Alleyne v. United States, 133 S.Ct. 2151 (2013). In this case, it is clear that drug quantity was an element of Rivera-Ruperto's charged drug offenses because the drug quantity findings increased Rivera-Ruperto's sentence beyond the statutory maximum for undetermined drug quantities. At trial, the judge did submit the drug quantity question to the jury, and also instructed the jury that the government was required to prove each element of the drug offenses beyond a reasonable doubt. But he never instructed the jury that drug quantity was an element of the drug crimes, nor did he ever state explicitly that drug quantity had to be found beyond a reasonable doubt. The question we must answer, then, is whether the jury nonetheless would have understood that it was required to apply the beyond-a-reasonable-doubt standard to its findings on drug quantity. We conclude that it did, and that the court therefore did not commit obvious error.

         In United States v. Barbour, 393 F.3d 82, 89 (1st Cir. 2004), a case involving similar facts, the district court failed, much like the court in this case, to instruct the jury that drug quantity was an element of the offense, although it should have done so. We concluded, however, that this failure did not constitute obvious error because the jury had been "clearly instructed that the defendant's guilt must be proven beyond a reasonable doubt" and subsequently told, albeit separately, that, if the jury found the defendant guilty, it would be required to make a drug quantity finding. Id. We reasoned that the instructions, while not perfect, sufficiently "connected that burden of proof to the drug quantity determination." Id. In addition, as in the present case, the verdict form contained a multiple-choice drug quantity question that immediately followed the question regarding the defendant's guilt. Id. Under those circumstances, we concluded that the district court had not committed plain error. Id.

         Likewise, here, although the judge never instructed the jury that it was required to make its drug quantity findings beyond a reasonable doubt (though, we stress, he should have), he correctly submitted the drug quantity question to the jury, instructed the jury more than once as to the government's beyond-a-reasonable-doubt burden, and instructed the jury that if it found Rivera-Ruperto guilty of a drug offense, it would also be required to make a drug quantity finding. Furthermore, on the verdict form, after each question that asked whether the jury found Rivera-Ruperto "guilty" or "not-guilty" of a drug-related offense, a question directing the jury to make a multiple-choice finding as to drug quantity immediately followed. Thus, the "link between the burden of proof and the jury's quantity determination, " id. at 89, was at least as close here as it was in Barbour.

         In arguing that the district court nonetheless committed plain error, Rivera-Ruperto relies on Delgado-Marrero, a case in which, applying plain error review, we remanded for resentencing on the basis of an Alleyne error. 744 F.3d at 186-90. In Delgado-Marrero, however, the district court had submitted drug quantity to the jury as a special verdict question only after the jury had already deliberated and returned its guilty verdict. Id. 186-87. The court never directed the jury to apply the beyond-a-reasonable-doubt standard to the special verdict question, nor did it instruct the jury that drug quantity was an element of the drug offense. Id. at 187. Under those circumstances, "given the timing and manner in which the [drug quantity] question was presented, " we reasoned that we could not find that the jury was "sufficiently put on notice of [the drug quantity question's] critical import to this case." Id. Because the jurors "had no cause to understand the special verdict question as involving another element of the offense, " we concluded that the court had obviously erred. Id.

         By contrast, here, as we have already noted, drug quantity was submitted to the jury in the initial jury instructions and on the verdict form, and the court explicitly instructed the jury that the government was required to prove its case beyond a reasonable doubt. Therefore, Rivera-Ruperto has not cleared the obvious-error hurdle.

         Moreover, even if we assumed that the district court's error was obvious and that it affected the defendant's substantial rights, [13] reversal still would not be warranted because Rivera-Ruperto cannot show that the error was sufficiently fundamental to threaten the fairness, integrity, or public reputation of the proceedings. See id. at 184. The evidence in this case that each of the staged drug deals involved more than 5 kilograms of sham cocaine was "overwhelming" and "essentially uncontroverted, " which gives us no basis for concluding that the judicial proceedings were so affected. United States v. Cotton, 535 U.S. 625, 633 (2002) (holding that the fourth plain-error-review requirement cannot be met where the evidence of an element was "overwhelming" and "essentially uncontroverted" at trial) (quoting Johnson v. United States, 520 U.S. 461, 470 (1997)).

         At trial, the government showed the jury video footage from each of the charged drug deals of a confidential informant weighing the bricks of sham cocaine, and then Rivera-Ruperto placing each brick into a suitcase. The same confidential informant also testified on the stand as to the number of kilograms of sham cocaine that were used during each deal. No conflicting evidence emerged at trial that might have possibly called into question the government's drug quantity evidence, and Rivera-Ruperto does not provide any argument on appeal as to how we might conclude that, given the evidence presented, any error on the district court's part threatened the fairness, integrity, or public reputation of his trial.

         Let us be clear: we think the district court's jury instructions were flawed, and that the judge should have instructed the jury that it was required to make its drug quantity findings beyond a reasonable doubt. But, as Rivera-Ruperto has not succeeded in climbing the steep road of plain error review, we cannot reverse.

         III. Sentencing Challenges

         Rivera-Ruperto's remaining two arguments are challenges to his sentence. He argues that the government engaged in improper sentencing manipulation when it set up the sting operation, and also that his resulting combined sentence between the two trials of 161 years and 10 months violated the Eighth Amendment's prohibition on cruel and unusual punishment. We begin for a final time by recounting what happened below.

         A. Background

         At the beginning of Rivera-Ruperto's sentencing hearing, defense counsel raised the issue of sentencing manipulation, arguing that the FBI had arbitrarily chosen to use "large" amounts (more than 5 kilograms) of sham cocaine for the sole purpose of enhancing Rivera-Ruperto's sentencing exposure. Defense counsel argued that, for each of the staged drug transactions, the elements of the charged offenses would have been fulfilled with lesser amounts of sham cocaine, and that the FBI's decision to use the 8-kilogram, 12-kilogram, and 15-kilogram quantities could only have been for purposes of "mere sentencing enhancement."

         Defense counsel also argued that the government's charging practices constituted impermissible sentencing manipulation because the series of five drug deals could have been charged as a single drug conspiracy, in which case Rivera-Ruperto would have been convicted of just one count of possession of a firearm in violation of 18 U.S.C. § 924(c), an offense that carries with it a mandatory minimum sentence of 5 years imprisonment, id. § 924(c)(1)(A). Instead, the government chose to charge each drug deal as a separate transaction, counsel contended, fully knowing that each "second or subsequent" conviction under the subsection carries with it a mandatory minimum sentence of 25 years imprisonment, id. ยง 924(c)(1)(C)(i), which ...

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