852 F.3d 1 (1st Cir. 2017), 12-2364, United States v. Rivera-Ruperto

Docket Nº:12-2364, 12-2367
Citation:852 F.3d 1
Opinion Judge:THOMPSON, Circuit Judge.
Party Name:UNITED STATES, Appellee, v. WENDELL RIVERA-RUPERTO, a/k/a Arsenio Rivera, Defendant, Appellant
Attorney:H. Manuel Hern
Judge Panel:Before Torruella, Lipez, and Thompson, Circuit Judges. TORRUELLA, Circuit Judge (Dissenting). TORRUELLA, Circuit Judge (Dissenting).
Case Date:January 13, 2017
Court:United States Courts of Appeals, Court of Appeals for the First Circuit

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852 F.3d 1 (1st Cir. 2017)



WENDELL RIVERA-RUPERTO, a/k/a Arsenio Rivera, Defendant, Appellant

Nos. 12-2364, 12-2367

United States Court of Appeals, First Circuit

January 13, 2017

As corrected January 24, 2017.

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[Copyrighted Material Omitted]

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H. Manuel Hernández for appellant.

Robert J. Heberle, Attorney, Public Integrity Section, Criminal Division, U.S. Department of Justice, with whom Francisco A. Besosa-Martí nez, 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. TORRUELLA, Circuit Judge (Dissenting).


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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

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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

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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

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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...

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