Court Opinion

ID: 4115817
Source: CourtListenerOpinion
Date Created: 2017-01-13 22:00:37.777428+00
Date Added: 2024-06-11T14:45:54.770269
License: Public Domain

United States Court of Appeals
                     For the First Circuit

Nos. 13-2017, 13-2047, 13-2072

                         UNITED STATES,

                            Appellee,

                                 v.

          WENDELL RIVERA-RUPERTO, a/k/a Arsenio Rivera,
                     MIGUEL SANTIAGO-CORDERO,
                      DAVIEL SALINAS-ACEVEDO,

                     Defendants, Appellants.

          APPEALS FROM THE UNITED STATES DISTRICT COURT
                 FOR THE DISTRICT OF PUERTO RICO

       [Hon. Carmen Consuelo Cerezo, U.S. District Judge]

                             Before

                 Torruella, Lipez, and Thompson,
                         Circuit Judges.

     H. Manuel Hernández for appellant Wendell Rivera-Ruperto.
     Ignacio Fernández de Lahongrais 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 Rodríguez-Vélez, United States Attorney,
were on brief, for appellee.
January 13, 2017

     - 2 -
          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-Ruperto   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.

                                 - 3 -
                                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,1 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

     1 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).

                                 - 4 -
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

                                 - 5 -
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-

Ruperto's first trial and sentencing.              Rivera-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.

                                       - 6 -
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, 132 S. Ct. 1376, 1384 (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

                                      - 7 -
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 Lafler 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

                                          - 8 -
          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.2

          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

     2 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 (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 Lafler claim, the claim still fails.

                                 - 9 -
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

                                       - 10 -
meet the two-part ineffective assistance of counsel test laid out

in Strickland v. Washington, 466 U.S. 668, 687 (1984). See Lafler,
132 S. Ct. at 1376.          Specifically, Rivera-Ruperto 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

                                    - 11 -
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)(1)(C)(i), to be served consecutively, id.

§ 924(c)(1)(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-Ruperto'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.3    After deliberating, the jury found

Rivera-Ruperto guilty of all counts.

     3 The verdict form, which Rivera-Ruperto did not object to,
simply stated: "We, the Jury, find defendant WENDELL RIVERA RUPERTO
___________ (GUILTY/NOT GUILTY) as charged in Count Eighteen of
the Indictment."

                                - 12 -
            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.4          See Delgado-Marrero,
744 F.3d at 184.

            In order to explain Rivera-Ruperto's argument, we must

first give a bit of background on the relevant case law.              At the

     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.
     4   Jury instruction challenges generally must be preserved at

                                  - 13 -
time of Rivera-Ruperto's second trial, the rule was (and still is,

as we explain in a moment) that "[o]ther 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 (2000) (emphasis added).        In making this

exception for prior convictions in Apprendi, the Supreme Court

deliberately left undisturbed its holding in Almendarez-Torres v.

United States, 523 U.S. 224, 226-27 (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 Alleyne v. United States, 133 S. Ct. 2151,

2155 (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

(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.1.

trial, but a defendant may preserve his challenge to an
instructional Apprendi/Alleyne 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.

                                - 14 -
            Despite this language in Alleyne itself, Rivera-Ruperto

argues before us that Alleyne made Almendarez-Torres inapplicable

to his case.     He seems to argue that, because Alleyne expanded the

Apprendi umbrella, bringing facts that increase mandatory minimums

under its shelter, we should, in keeping with the spirit of

Alleyne, 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

prior 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

Almendarez-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-

                                        - 15 -
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,

                                - 16 -
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.5         See Sánchez-Berríos, 424 F.3d 65 at 78.

      5 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

                                         - 17 -
              Rivera-Ruperto argues that the government engaged in

sentencing manipulation by using unnecessarily high quantities of

sham drugs 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-Ruperto 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

second sentence. The government, however, does not argue waiver
in its brief. Thus, favorably to Rivera-Ruperto, we review for
plain error.

                                      - 18 -
prohibition on cruel and unusual punishment.        Here, Rivera-Ruperto

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

                                  - 19 -
("Rullán-Santiago")6 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 drug

traffickers and was "basically a delinquent using up the uniform."

It was Rullán-Santiago 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

       6
       Rullán-Santiago was one of the co-defendants in this case
below, but is not a party to this appeal.

                                       - 20 -
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.       Rullán-Santiago responded, "[L]et

me see if, . . . if that dog is around here."             Camacho replied,

                                   - 21 -
"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.7

             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.

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

                                  - 22 -
             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-Santiago 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 Rullán-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

                                    - 23 -
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 unpreserved 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.

                                 - 24 -
           The judicially-created doctrine of entrapment exists "to

prevent 'abuse[]' 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 (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-Berríos, 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.

                                    - 25 -
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

                                     - 26 -
Rullán-Santiago,    if    not    both    middlemen,8      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.9         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

     8 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.
     9 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").

                                      - 27 -
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-

                                     - 28 -
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-Pérez    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 Rullán-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

                                    - 29 -
produce   sufficient    evidence    of   government   overreach      or   arm-

twisting in this case.10

           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

     10 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
purported 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.

                                   - 30 -
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

                                    - 31 -
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-

                                        - 32 -
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

                                       - 33 -
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

                                   - 34 -
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 "support[ed] 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

                                 - 35 -
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-Acevedo.

             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

                                     - 36 -
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.

                       -Dissenting Opinion Follows-

                                  - 37 -
           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,

                              -- 38 --
get that guy," "find, find that guy," and, once more, "[f]ind 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.11

          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

     11Because 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.

                               -- 39 --
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.12

       12Another example of improper inducement is "dogged
insistence until [defendant] capitulated". Gendron, 18 F.3d at
961 (quoting United States v. Rodriquez, 858 F.2d 809, 815 (1st
Cir. 1988)(alteration in original); see also United States v.

                                 -- 40 --
              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 . . .

Montoya, No. 15-2089, 2016 WL 7336577, at *2 (1st Cir. Dec. 19,
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."

                                 -- 41 --
          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 (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 (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 (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)(emphasis added in original).

          I respectfully dissent.

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