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.
- 16 -