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

(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

(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,

(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.,

, 395

- 6 - (1948); see United States v. Barbour,

(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,

(1st Cir. 1995). A defendant bears

the burden of proving sentencing manipulation by a preponderance

of the evidence, United States v. Gibbens,

, 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,

(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,

(1st Cir.

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

the government to obtain a sentencing reduction. Montoya,

(quoting Gibbens,

). 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."

(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,

(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,

(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,

; United States

v. Jaca-Nazario,

(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,

.

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,

. Further, any purported illicit motive must be actions taken

out of "malice or bad faith." United States v. Capelton,

(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,

-

59 (explaining defendant's predisposition is secondary because

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

issue); see Gibbens,

n.3 (acknowledging potential

relevance of predisposition evidence when evaluating government

conduct or motives); United States v. Fontes,

(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,

; see Montoya,

(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,

(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,

(1st Cir.

2019) (quoting Anderson v. City of Bessemer,

(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,

, 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,

. 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,"

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.,

(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

(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 -