Court Opinion

ID: 9351315
Source: CourtListenerOpinion
Date Created: 2022-12-29 22:00:48.630057+00
Date Added: 2024-06-11T16:59:32.466513
License: Public Domain

United States Court of Appeals
                      For the First Circuit

No. 22-1063

                    UNITED STATES OF AMERICA,

                            Appellee,

                                v.

              SANTO BENITO LARA, a/k/a Luis Anaya,

                      Defendant, Appellant.

          APPEAL FROM THE UNITED STATES DISTRICT COURT
               FOR THE DISTRICT OF NEW HAMPSHIRE

         [Hon. Joseph N. Laplante, U.S. District Judge]

                              Before

                   Lynch, Thompson, and Gelpí,
                         Circuit Judges.

     Donna J. Brown, with whom Michael G. Eaton and Wadleigh, Starr
& Peters, P.L.L.C. were on brief, for appellant.
     Alexander S. Chen, Assistant United States Attorney, with
whom Jane E. Young, United States Attorney, and Seth R. Aframe,
Assistant United States Attorney, were on brief, for appellee.

                        December 29, 2022
            GELPÍ, Circuit Judge.        Defendant-Appellant Santo Benito

Lara ("Benito Lara") was tried and convicted of conspiracy to

distribute and to possess with the intent to distribute fentanyl,

in violation of 21 U.S.C. §§ 841(a)(1), 846.               On appeal, Benito

Lara challenges the district court's imposition of a ten-year

mandatory minimum sentence, contending that the district court

erred when it rejected his sentencing factor manipulation claim.

We affirm.

                               I. Background

                                     A. Facts

            On May 4, 2018, New Hampshire State Police conducted a

traffic    stop   and    discovered    771 grams    of   methamphetamine   and

141 grams of ecstasy (also known as MDMA) concealed within the

vehicle.     The driver, Confidential Source 1 ("CS1"), agreed to

cooperate with law enforcement and disclosed that in addition to

methamphetamine and MDMA, CS1 also dealt heroin and fentanyl.              CS1

admitted to buying half to one kilogram of fentanyl every week

from his supplier, "Mamma" -- later identified by law enforcement

as Maria     Mauras ("Mauras").         That    same day, law enforcement

directed CS1 to contact Mauras and arrange to purchase seventy-

three    fingers1   of    fentanyl    for     approximately   $16,000.     Law

     1 A "finger" or "stick" is ten grams of powdered fentanyl sold
in compressed, cylindrical packaging.

                                      - 2 -
enforcement then met Mauras at a Target in Salem, New Hampshire,

and conducted a buy bust2 that led to her arrest.

          Mauras   consequently   agreed   to   cooperate   with   law

enforcement and identified "Louie"3 -- aka Benito Lara -- as the

source of the fentanyl.   At agents' request, she contacted Benito

Lara and set up a meeting for the following day.      Intending said

meeting to be another buy bust, agents instructed Mauras to order

sixty fingers of fentanyl, or 600 grams.    After several telephone

conversations between Mauras and Benito Lara about where the

transaction would occur, Benito Lara instructed Mauras to meet him

at 107 Summer Street in Lawrence, Massachusetts.        When Mauras

arrived, she could not reach Benito Lara.         As a result, law

enforcement called off the staged transaction (this is referred to

as "the failed buy bust").

          After the failed buy bust on May 10, agents switched

tactics and began using Mauras for smaller controlled buys -- the

first of which occurred on May 30, 2018.           That day, Mauras

successfully purchased ten fingers, or 100 grams, of fentanyl from

Benito Lara.   From there, again using Mauras, agents conducted

     2 A "buy bust" is when law enforcement engages in the purchase
of a controlled substance and the seller is arrested upon the
completion of the sale.
     3During the investigation and trial, Benito Lara was referred
to as "Louie Anaya" or "Luis Anaya." Any reference in the record
to "Louie," "Luis," or "Anaya" has been changed here to Benito
Lara for clarity.

                              - 3 -
eight additional buys of varying quantities of fentanyl -- ranging

from       30   to   100 grams -- from     two   addresses   in    Lawrence,

Massachusetts -- 83 Walnut Street and 107 Summer Street -- with

the final transaction occurring on September 11, 2018.

                On October 4, 2018, Benito Lara and his codefendant,

Guedin Nivar Baez4 ("Nivar Baez"), were arrested for conspiracy to

distribute fentanyl.5       The same day, search warrants were executed

on 107 Summer Street, Apt. 4H, Lawrence, Massachusetts (Benito

Lara's      apartment)   and   36 Hudson    Avenue,   3rd Floor,   Lawrence,

Massachusetts (a suspected stash house where Nivar Baez would

travel between buys).6          Benito Lara and Nivar Baez were each

indicted on one count of conspiracy to distribute and to possess

with the intent to distribute fentanyl, in violation of 21 U.S.C.

§§ 841(a)(1), 846.

       Nivar Baez was stopped by law enforcement during the
       4

investigation and provided a driver's license with the false name
"Jhonatan Mateo." Any reference in the record to "Jhonatan" or
"Mateo" has been changed here to Nivar Baez for clarity.
       During the investigation, Nivar Baez was identified
       5                                                                 as
Benito Lara's drug runner.      A drug runner is a person               who
transports controlled substances to the location where                  the
transaction is set to occur. They are often used to insulate            the
dealer from police investigation or to prevent drug rip-offs.
       Although seven of the nine controlled buys occurred at
       6

83 Walnut Street, Lawrence, Massachusetts, the transactions
occurred immediately inside the doorway. Law enforcement did not
believe they could obtain a search warrant for 83 Walnut Street
based on that evidence because the property is not a single-family
residence.

                                    - 4 -
                           B. Procedural History

              After a four-day jury trial, Benito Lara was found guilty

of conspiracy to distribute and to possess with the intent to

distribute fentanyl.7        In advance of sentencing, the probation

officer submitted a presentence investigation report ("PSR") that

Benito Lara successfully objected to three aspects of: (1) the

drug       quantity   calculation,     (2)   an    upward    adjustment   for

maintaining      drug   distribution     premises,     and   (3)   an   upward

adjustment for being an organizer or leader in the criminal

activity.8       After accounting for the sustained PSR objections,

Benito Lara's Guidelines sentencing range was 97 to 121 months,

and he faced a ten-year mandatory minimum.

              Benito Lara, however, also raised a claim of sentencing

factor manipulation and sought an equitable downward departure

from the mandatory minimum sentence.              The district court held a

second sentencing hearing on November 4, 2019, and concluded that

based on the original and supplemental briefings, Benito Lara had

not met his burden of establishing sentencing factor manipulation

but live testimony from the investigating agents was needed to

      Nivar Baez pled guilty and was sentenced to fifty-two months
       7

of imprisonment.
       The district court declined to attribute the 700 grams of
       8

fentanyl sold by Mauras on May 4, 2018, at Target to Benito Lara.
Additionally, the government agreed to striking the two-level
adjustment for Benito Lara being a leader or manager.

                                     - 5 -
conclusively decide the issue.    As a result, United States Drug

Enforcement Administration Agent John Daly ("Agent Daly") and Task

Force Officer Robert Lukacz ("TFO Lukacz") testified about their

knowledge of federal sentencing, specifically mandatory minimums,

and detailed any direction received from superiors about how to

conduct their investigation.     They were questioned extensively

about their motivations for investigating Benito Lara and their

justifications for the strategies employed.    On January 10, 2022,

the district court denied Benito Lara's request for a departure

from the mandatory minimum sentence, citing his failure to prove

the existence of sentencing manipulation, and sentenced him to

120 months of imprisonment (the mandatory minimum).    This timely

appeal followed.

                      II. Standard of Review

          We review a district court's determination of whether

sentencing factor manipulation occurred for clear error.    United

States v. Gibbens, 25 F.3d 28, 30 (1st Cir. 1994) (categorizing

manipulation decision as "factbound").     "A [district court's]

finding is 'clearly erroneous' when although there is evidence to

support it, the reviewing court on the entire evidence is left

with the definite and firm conviction that a mistake has been

committed."   United States v. U.S. Gypsum Co., 333 U.S. 364, 395

                               - 6 -
(1948); see United States v. Barbour, 393 F.3d 82, 86 (1st Cir.

2004) (same).

                              III. Discussion

            Sentencing factor manipulation occurs "where agents have

improperly enlarged the scope or scale of the crime."                  United

States v. Montoya, 62 F.3d 1, 3 (1st Cir. 1995).        A defendant bears

the burden of proving sentencing manipulation by a preponderance

of the evidence, United States v. Gibbens, 25 F.3d at 31-32, and

cannot prevail "simply by showing that the idea originated with

the government[,] . . . that the conduct was encouraged by it, or

that the crime was prolonged beyond the first criminal act, or

exceeded in degree or kind what the defendant had done before."

Montoya, 62 F.3d at 3-4 (citations omitted) (explaining "garden

variety"   claims   of   sentencing     manipulation   inevitably      fail).

Because    "there   is   an   element   of   manipulation   in   any   sting

operation," United States v. Connell, 960 F.2d 191, 194 (1st Cir.

1992), a defendant must establish "extraordinary misconduct" by

the government to obtain a sentencing reduction.         Montoya, 62 F.3d

at 4 (quoting Gibbens, 25 F.3d at 31).        As Montoya explains, "[t]he

standard is high because we are talking about a reduction at

sentencing, in the teeth of a statute or guideline approved by

Congress, for a defendant who did not raise or did not prevail

upon an entrapment defense at trial."             Id. (emphasis added).

Additionally, "[t]he standard is general because it is designed

                                   - 7 -
for   a   vast     range   of   circumstances     and    of    incommensurable

variables."      Id.; see Gibbens, 25 F.3d at 31 (declining to create

bright line rule and instead requiring individualized assessment

of manipulation claims). Our case law makes clear that "sentencing

factor manipulation is a claim only for the extreme and unusual

case."    See Montoya, 62 F.3d at 4 (emphasis added).

           When a sentencing factor manipulation claim is raised,

a district court's primary inquiry should be "the government's

conduct    and      motives"    in   deciding     whether       "extraordinary

misconduct" occurred.       See Gibbens, 25 F.3d at 31; United States

v. Jaca-Nazario, 521 F.3d 50, 58 (1st Cir. 2008).               "Extraordinary

misconduct" may take the form of an "illegitimate motive on the

part of the agents" or "outrageous or intolerable pressure" from

government actors on the accused.             See Montoya, 62 F.3d at 4.

Because    a     finding   of   "extraordinary    misconduct"       is   deeply

intertwined with the facts, we extend deference "even to the

district court's conclusion about whether or not the government

has behaved outrageously or intolerably."             Jaca-Nazario, 521 F.3d

at 57. Further, any purported illicit motive must be actions taken

out of "malice or bad faith."        United States v. Capelton, 350 F.3d

231, 246 (1st Cir. 2003).        If any government misconduct is found,

the   court's      secondary    inquiry      should     be    the   defendant's

predisposition to commit the crime.          Jaca-Nazario, 521 F.3d at 58-

59 (explaining defendant's predisposition is secondary because

                                     - 8 -
with guilt already established, only degree of criminality is at

issue); see Gibbens, 25 F.3d at 31 n.3 (acknowledging potential

relevance of predisposition evidence when evaluating government

conduct or motives); United States v. Fontes, 415 F.3d 174, 183

(1st    Cir.       2005)    (affirming     consideration          of     predisposition

evidence      in    determining     whether      the    government's       conduct    was

"extreme and outrageous"). If manipulation is found, a "sentencing

court   has    ample       power   to   deal    with    the   situation      either   by

excluding the tainted transaction from the computation of relevant

conduct or by departing from the [Guidelines sentencing range]."

Connell, 960 F.2d at 196; see Montoya, 62 F.3d at 4 (stating

departure for sentencing factor manipulation is permitted even

where mandatory minimum applies).

              On appeal, Benito Lara faces an uphill battle given the

high standard for sentencing manipulation claims and the deference

afforded      to    the    district     court's    "factbound"          determinations.

Nevertheless,        he     contends     that     the    record        demands   finding

sentencing factor manipulation and, consequently, a sentence below

the ten-year mandatory minimum.                 Benito Lara marshals many facts

to claim that law enforcement improperly expanded the scope of his

crime, and although not so explicitly stated, we understand that

he advances         two theories: (1)          Law enforcement acted with an

improper investigative motive in extending their investigation

until Benito Lara sold threshold quantity amounts of fentanyl, and

                                         - 9 -
(2) Benito Lara was not predisposed to selling large quantities of

fentanyl, but his will was overborn by law enforcement. We address

each in turn.

                 A. Law Enforcement Improper Motive Claim

            First,     Benito       Lara    argues     that   law    enforcement's

investigation was motivated by a desire to turn him into the "big

fish" that Mauras promised them.            He argues that the May 10 failed

buy bust establishes that agents knew he was a street-level dealer

and ignored critical evidence that they were moving "down the

chain."   He further claims that, when agents were unable to arrest

him for selling 600 grams of fentanyl, they conducted nine smaller

controlled   buys      until   he    sold    over    400 grams -- the      ten-year

mandatory    minimum     threshold -- thus           acting   upon   an    improper

motive.

            It    is   settled       law    that     the   government     does   not

impermissibly enlarge a sentence simply by inviting the defendant

to engage in multiple drug sales, as opposed to arresting him after

the first sale.          See Capelton, 350 F.3d at 246 (emphasizing

sentencing manipulation requires government to act out of "malice

or bad faith").        As such, the government engaging Benito Lara in

nine controlled buys alone does not constitute sentencing factor

manipulation.

            Nor does Benito Lara establish that the government acted

in bad faith or based on an improper motive.                  The district court

                                       - 10 -
accepted as credible the testimony of Agent Daly and TFO Lukacz,

who were both subjected to extensive cross examination. Therefore,

we summarize below the evidence before the district court when it

reached that conclusion.

             Per Agent Daly, the May 10 buy bust likely failed because

Benito Lara was spooked by the change in pattern following the

Target bust: Mauras not returning with the cash on May 4, being

out of touch for days, and then attempting to get him to go to a

new location on May 10 where deals had never previously occurred.

Law enforcement switched to smaller quantities after the failed

buy   bust    to    reestablish     Benito    Lara's     trust    in   Mauras.

Additionally,      as   justification   for   continuing    to    investigate

Benito Lara, Agent Daly explained that despite the failed buy bust,

he still believed Benito Lara could obtain a large quantity of

drugs because, outside of Mauras identifying him as her source,

she was surveilled going to 107 Summer Street immediately before

the Target buy bust.        Agent Daly also testified that during the

window from May 10 to May 30, he met with Mauras and received new

information    prompting    an    investigation   into    the    broader   drug

trafficking organization ("DTO") that Benito Lara was believed to

be a part of.      Further, law enforcement only learned that Benito

Lara used a drug runner during the first successful buy on May 30.

Both agents testified that the additional controlled buys were

motivated by a desire to gather evidence, get the DTO's pattern of

                                    - 11 -
operation down, positively identify Benito Lara and the drug

runner, Nivar Baez, locate potential stash houses for drugs or

cash, and develop probable cause for search warrants of the three

involved properties, particularly 107 Summer Street where Mauras

had observed drugs and where the failed buy bust was supposed to

occur.

            As we have      previously stated,       "[i]f . . . a judge's

finding is based on witness credibility, that finding, 'if not

internally inconsistent, can virtually never be clear error.'"

United States v. Rivera-Carrasquillo, 933 F.3d 33, 42 (1st Cir.

2019) (quoting Anderson v. City of Bessemer, 470 U.S. 564, 575

(1985)).    Here, Agent Daly and TFO Lukacz provided justifications

for the change in strategy and continued investigation that are

facially    reasonable.       Nevertheless,    Benito       Lara    claims   that

internal factual inconsistencies exist which undermine the agents'

credibility.

            Benito     Lara     asserts       that     law         enforcement's

justifications for the length of the investigation are nothing

more     than   "backward   rationalizations"        that    demonstrate     the

government's lack of good faith.       He posits that all the evidence

law enforcement needed to arrest and obtain search warrants was

known by May, or at the latest, July; yet, agents continued the

controlled buys until September when he was comfortably over the

400-gram mandatory minimum threshold.           Further, he alleges that

                                  - 12 -
law enforcement failed to meaningfully investigate the DTO or

gather additional evidence, undermining one of law enforcement's

main     justifications      for   extending        the       investigation      until

September.     Despite Benito Lara's assertions, TFO Lukacz testified

that   law    enforcement    could    not    obtain       a   search   warrant    for

107 Summer     Street    until     they     knew     Benito      Lara's      apartment

number -- a statement credited by the district court -- because

buys did not occur there again until August 2018 and Mauras,

although able to describe the apartment's interior in detail, did

not know the apartment number within the "carved up tenement."

Once law enforcement obtained the apartment number following the

final buy on September 11, the controlled buys stopped. TFO Lukacz

also testified as to investigative steps, unfruitful as they may

have been, that were taken to develop evidence in addition to

controlled     buys   with   Benito    Lara:       surveillance,       phone    record

analysis, and controlled buys with another potential DTO member.

             Here, the district court took great care in considering

Benito       Lara's     sentencing        manipulation          claim -- receiving

substantial briefing, as well as live testimony from the agents

about why the investigation was prolonged.                     The district court

questioned officers directly about their investigative motives and

the    evidence   the     investigation      produced.            We   see     nothing

"internally inconsistent" in the district court crediting the

agents' testimony when it was not contradicted by "documents or

                                      - 13 -
objective evidence," Anderson, 470 U.S. at 575, but merely by

Benito   Lara's   differing   interpretation    of   the   facts.   The

government's good faith justifications for the length of the

investigation, accepted by the district court, are "at least as

plausible" as the improper motive attributed to law enforcement by

Benito Lara.   See Gibbens, 25 F.3d at 32.     Because "[w]e have held,

time and again, that when a sentencing court is confronted with

two reasonable views of the record, and chooses to credit one such

view rather than the other, its choice cannot be termed clearly

erroneous," id., we affirm the district court's rejection of Benito

Lara's sentencing factor manipulation claim.         The district court

did not clearly err when it found that Benito Lara failed to

establish an improper government motive.

               B. Excessive Government Pressure Claim

           Second, Benito Lara contends that law enforcement used

"excessive pressure" to overbear his         will since he was only

predisposed to committing lesser crimes -- in other words, selling

smaller quantities of fentanyl.          But none of his contentions

persuade us.

           In support of his excessive pressure claim, Benito Lara,

argues that because Mauras entered into such a favorable deal with

his alleged boss, Julio Perez ("Perez"), Benito Lara had no choice

but to provide Mauras drugs and collect the proceeds to send to

Perez.   Unfortunately for Benito Lara, he raises this argument for

                                - 14 -
the first time on appeal -- a point the government made in its

brief and Benito Lara left uncontradicted when he failed to file

a reply brief.           "[A]bsent extraordinary circumstances counseling

for exception, we routinely deem waived arguments not timely

presented before the district court."               Butler v. Deutsche Bank Tr.

Co Ams., 748 F.3d 28, 36 (1st Cir. 2014).                    Because Benito Lara

never       convincingly      explains       how    his     situation     fits      the

extraordinary-circumstances exception, we decline to entertain his

Perez argument for the first time on appeal.

                By way of further example, Benito Lara also asserts that

law enforcement overbore his will because he was not someone who

had previously dealt in "very substantial quantities."                         He cites

his single prior arrest for selling 10 grams of fentanyl and modest

lifestyle -- living in a small, minimally furnished attic room and

possessing a flip phone -- as evidence that he was only predisposed

to being a low-level street dealer.                But the record does not bear

out       his   suggestion.       As     the    government      notes -- with        no

contradiction from Benito Lara -- he sold Mauras fentanyl nine

separate        times,    including    100 grams     on     three    occasions      and

50 grams on three occasions.                   Any one of those transactions

(notably,        the      first   controlled        buy     conducted      in      this

investigation) would have been sufficient to subject Benito Lara

to    a    five-year      mandatory    minimum      sentence,       see   21     U.S.C.

§ 841(b)(1)(B)(vi),          belying   his      assertion    that    he   only     sold

                                       - 15 -
threshold    quantities   of    fentanyl   after    being   subjected   to

excessive pressure from law enforcement.           We see no clear error

here either.

                               IV. Conclusion

            For the foregoing reasons, the district court's judgment

is affirmed.

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