FROM THE UNITED STATES DISTRICT COURT FOR THE DISTRICT OF
PUERTO RICO [Hon. Juan M. Pérez-Giménez, U.S.
Manuel Hernández for appellant.
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.
Torruella, Lipez, and Thompson, Circuit Judges.
THOMPSON, Circuit Judge.
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. 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
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. 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.
reasons stated below, we affirm the district court.
our summary of the facts brief for now, saving the specific
details related to Rivera-Ruperto's various challenges
for our later discussion.
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.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. 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.
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
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.
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
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
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,
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.
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.
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.
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.
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.
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
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. 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).
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.
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
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
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.
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
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]."But this argument fails on both
Strickland requirements. To start, Rivera-Ruperto
has failed to establish that Aguayo's performance was
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)).
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
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.
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.
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.
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.
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.
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.
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
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."
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."
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.
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. 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).
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
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).
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.
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.
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.
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.
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
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.
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.
even if we assumed that the district court's error was
obvious and that it affected the defendant's substantial
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)).
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.
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.
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.
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."
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. § 924(c)(1)(C)(i),