19-3834-cr United States v. Khan

UNITED STATES COURT OF APPEALS FOR THE SECOND CIRCUIT

SUMMARY ORDER Rulings by summary order do not have precedential effect. Citation to a summary order filed on or after January 1, 2007, is permitted and is governed by Federal Rule of Appellate Procedure 32.1 and this court’s Local Rule 32.1.1. When citing a summary order in a document filed with this court, a party must cite either the Federal Appendix or an electronic database (with the notation “summary order”). A party citing a summary order must serve a copy of it on any party not represented by counsel. At a stated term of the United States Court of Appeals for the Second Circuit, held at the Thurgood Marshall United States Courthouse, 40 Foley Square, in the City of New York, on the 5th day of May, two thousand twenty-one.

PRESENT: Robert D. Sack, Steven J. Menashi, Circuit Judges, Lewis A. Kaplan, Judge. 1 ____________________________________________

United States,

Appellee,

v. No. 19-3834

Shahbaz Khan,

Defendant-Appellant, ___________________________________________

1Judge Lewis A. Kaplan of the United States District Court for the Southern District of New York, sitting by designation. For Appellee: Jason A. Richman, Rebekah Donaleski, and Anna M. Skotko, Assistant United States Attorneys, for Audrey Strauss, United States Attorney for the Southern District of New York, New York, NY.

For Defendant-Appellant: Randall D. Unger, Kew Gardens, NY.

Appeal from a judgment of the United States District Court for the Southern

District of New York (Schofield, J.).

Upon due consideration, it is hereby ORDERED, ADJUDGED, and

DECREED that the judgment of the district court is AFFIRMED.

On May 31, 2018, Defendant-Appellant Shahbaz Khan pleaded guilty,

without the benefit of a plea agreement, to the two-count superseding indictment

charging him with conspiracy to import narcotics to the United States and

attempted narcotics importation in violation of

, 952, 959, 960, and

963, and

. Khan appeals the sentence imposed on November 5,

2019, by the United States District Court for the Southern District of New York, of

180 months’ imprisonment to be followed by a five-year term of supervised

release. He argues that the sentence is procedurally unreasonable because the

district court failed to consider Khan’s imperfect entrapment argument and that

2 his below-guidelines sentence of 15 years’ imprisonment is substantively

unreasonable. We disagree and affirm. We assume the parties’ familiarity with the

underlying facts, procedural history, and arguments on appeal.

BACKGROUND

A

In mid-2016, the Drug Enforcement Administration (“DEA”) opened an

investigation into Defendant-Appellant Shahbaz Khan. Khan met with

confidential sources working for the DEA who posed as drug traffickers seeking a

new heroin supplier for a purported New York-based customer, who in fact was

an undercover DEA officer. At their first meeting in August 2016, which was

recorded, Khan told the confidential sources about his experience as an

international narcotics trafficker, which included supplying more than 114 tons of

drugs in one year, including 64 tons of hashish and 50 tons of “baeest” (a Pashtu

slang word for either heroin or morphine, a heroin precursor). Khan told them that

he had a drug trafficking system “that would have functioned for the next twenty

years” had it not been disrupted when Khan and his former drug-trafficking

partner were arrested, and Khan was imprisoned for seven years. Khan

communicated that he was eager to resume his business. Later that month, Khan

3 spoke with the undercover officer, who introduced himself as a New York-based

customer. He asked Khan to assist in a money transfer of $100,000 from Australia

to New York, and they made plans to meet and discuss their heroin trafficking

scheme.

In September 2016, Khan met with the undercover officer and confidential

sources again. During these meetings, which were recorded, Khan agreed to

supply large quantities of heroin in maritime shipping containers from Pakistan

to New York. Khan discussed his methods to distribute large quantities of heroin

without detection. Khan was confident that he could ship narcotics “wherever you

give me an address[.] If you tell me America, I will send it to America.”

Khan further discussed the average cost of a kilogram of heroin in New York

City, and estimated profits of tens of thousands of dollars per kilogram. As proof

of the quality of his heroin supply, Khan agreed to sell a five-kilogram sample of

heroin for $4,000 per kilogram, which the undercover operative would then be

responsible for transporting from Kabul, Afghanistan, to New York. In October

2016, Khan, his drug courier, and the confidential sources met in Kabul and

exchanged five kilograms of heroin for the agreed upon payment of $4,000 per

kilogram.

4 In November 2016, Khan and one of his sons traveled to Nairobi, Kenya, to

meet with the undercover officer to further discuss the logistics of their

international heroin trafficking scheme. From there, the undercover officer and

Khan traveled together to Liberia. As they traveled to Liberia, Khan told the officer

that they could ship up to 10,000 kilograms of heroin at a time; that with 10,000

kilograms of heroin, “you can even pay off the president” of Pakistan; and that

Pakistani police would assist in the scheme by transporting heroin to the ports for

shipment. When they landed in Liberia on December 1, 2016, the local authorities

arrested Khan, and the DEA took him into custody and transported him to the

United States soon thereafter.

B

On May 14, 2018, a superseding indictment charged Khan in two counts for

conspiracy to import narcotics to the United States and importing narcotics in

violation of

, 952, 959, 960, and 963. On May 31, 2018, without the

benefit of a plea agreement, Khan pleaded guilty to both counts of the superseding

indictment.

Khan was sentenced on November 5, 2019. The district court began the

sentencing hearing by resolving certain disputes regarding the sentencing

5 guideline calculations that the parties had raised in their sentencing submissions.

As relevant here, the district court rejected Khan’s imperfect entrapment argument

and denied his request to depart or vary from the guideline sentence on that basis.

However, the district court noted that “in assessing the nature and circumstances

of the offense, [it was] considering that the US government agents proposed the

quantities, the drug, and the ultimate destination, which made up important

aspects of the conspiracy.” App’x 224.

After the district court ruled on these disputes, both parties affirmed that

there were no further objections to the district court’s sentencing guidelines

calculations. Khan faced a guidelines range of 292 to 365 months’ imprisonment.

The district court concluded that Khan’s offense conduct, even without

considering his prior arrest history, was “incredibly serious” given the “huge

quantities of heroin” and the impact of heroin on society. App’x 239. The district

court also noted that deterring Khan and other drug kingpins from importing

large amounts of drugs to the United States weighed in favor of a serious sentence

but that “10 years in prison is itself a very serious sentence and no less so for a man

who is 71 years old.” App’x 240. The district court observed that Khan was

assessed to be in relatively good health given his age. Finally, the district court

6 explained that it was not sentencing Khan for his prior drug trafficking activity

but noted that:

[T]his was not something that first occurred to you when you were approached by the agents. It was not something that was foreign to you. And in fact, you boasted about your prior drug trafficking, and whether or not there was some element of puffery in it, it’s clear that you were an experienced drug trafficker and that’s what you were prepared to do in this case.

App’x 241. Noting his advanced age, and that a guidelines sentence would

effectively be a life sentence, the district court sentenced Khan principally to a

below-guidelines term of 180 months’ imprisonment to be followed by a five-year

term of supervised release. Khan timely appealed.

DISCUSSION

Khan argues that (1) his sentence is procedurally unreasonable because the

district court failed to consider Khan’s imperfect entrapment argument and (2) his

below-guidelines sentence of 15 years’ imprisonment is substantively

unreasonable. We reject both arguments.

A

Sentencing challenges are reviewed for “reasonableness,” which is “‘a

particularly deferential form of abuse-of-discretion review’ that we apply both to

7 the procedures used to arrive at the sentence (procedural reasonableness) and to

the length of the sentence (substantive reasonableness).” United States v. Broxmeyer,

(2d Cir. 2012) (quoting United States v. Cavera,

, 188

n.5 (2d Cir. 2008) (en banc)).

A district court commits procedural error by “failing to calculate (or

improperly calculating) the Guidelines range, treating the Guidelines as

mandatory, failing to consider the § 3553(a) factors, selecting a sentence based on

clearly erroneous facts, or failing to adequately explain the chosen sentence—

including an explanation for any deviation from the Guidelines range.” United

States v. Dorvee,

(2d Cir. 2010) (quoting Gall v. United States,

(2007)). Adequately explaining the chosen sentence is “a low

threshold,” United States v. Rosa,

(2d Cir. 2020), because “there is

no requirement that the court mention the required factors, much less explain how

each factor affected the court’s decision,” United States v. Banks,

(2d Cir. 2006). “The ‘context and the record’ may render a district court’s

explanation adequate even where ‘the judge might have said more.’” Rosa,

(quoting Rita v. United States,

(2007)).

8 A departure from the sentencing guidelines range for imperfect entrapment

is based on “conduct by the government that does not give rise to an entrapment

defense but that is nonetheless ‘aggressive encouragement of wrongdoing.’”

United States v. Bala,

(2d Cir. 2000). A downward departure on this

ground is warranted if the district court determines that this factor “takes the case

outside the heartland of the applicable Guideline.”

(quoting Koon v. United

States,

(1996)).

Khan argues that his sentence was procedurally unreasonable because the

district court “failed to adequately consider or rule on” his claim of imperfect

entrapment as either a basis for a downward departure or a mitigating factor

under § 3553(a). Appellant’s Br. 12. The record at sentencing contradicts his

argument. The district court expressly considered the imperfect entrapment

argument and declined to use it as a basis for a downward departure. App’x 224.

The district court acknowledged that it would consider, “in assessing the nature

and circumstances of the offense ... that the US government agents proposed the

quantities, the drug, and the ultimate destination, which made up important

aspects of the conspiracy.” Id.

9 In its statement of reasons, moreover, the district court again addressed the

imperfect entrapment argument, noting that drug trafficking was “not something

that first occurred to [Khan] when [he was] approached by the agents.” App’x 241.

The district court observed that drug trafficking was not “foreign” to Khan and

that he had “boasted” about his prior drug trafficking experience to the

undercover agent and confidential sources. Id. The district court concluded that it

was “clear” that Khan was an “experienced drug trafficker” and was prepared to

apply his experience to effectuate the scheme. Id.

In sum, the district court considered and rejected Khan’s imperfect

entrapment argument and therefore did not err procedurally under any standard

of review. 2

B

Next, Khan argues that his sentence was substantively unreasonable

because the district court failed to consider, under the § 3553(a) factors, (1) that his

2 The government seems to argue that the procedural reasonableness of the sentence should be reviewed for plain error because defense counsel answered in the negative when asked by the court if there were any further objection to its guidelines calculation before proceeding to sentencing. See App’x 224. Khan argues that this court reviews for reasonableness. Appellant’s Br. at 11-12. In any event, the district court did not procedurally err under either an abuse of discretion or a plain error standard.

10 statements asserting that he could deliver hundreds of kilograms of heroin were

puffery; (2) his age and medical history; and (3) that he would be exposed to

Covid-19 in prison. “[O]ur review of a sentence for substantive reasonableness is

particularly deferential.” Broxmeyer,

. This “deference derives from

a respect for [the district court’s] distinct institutional advantages” including its

“unique factfinding position, which allows it to hear evidence, make credibility

determinations, and interact directly with the defendant …, thereby gaining

insights not always conveyed by a cold record.”

Bearing these advantages in mind, “if the ultimate sentence is reasonable

and the sentencing judge did not commit procedural error in imposing that

sentence, we will not second guess the weight (or lack thereof) that the judge

accorded to a given factor or to a specific argument made pursuant to that factor.”

United States v. Pope,

(2d Cir. 2009) (alteration omitted). We

therefore “set aside a district court’s substantive determination only in exceptional

cases where the trial court’s decision cannot be located within the range of

permissible decisions.” United States v. Cavera,

(2d Cir. 2008) (en

banc) (internal quotation marks omitted). Because “[i]n the overwhelming

majority of cases, a Guidelines sentence will fall comfortably within the broad

11 range of sentences that would be reasonable in the particular circumstances,” it is

“difficult to find that a below-Guidelines sentence is unreasonable.” United States

v. Perez-Frias,

(2d Cir. 2011).

Khan’s below-guidelines sentence was well within the range of permissible

decisions, taking into account the seriousness of his conduct as well as his personal

circumstances. The district court considered and rejected Khan’s argument that his

statements about the extent of his distribution capabilities were mere puffery. In

rejecting his argument, the district court noted that trafficking drugs was not

foreign to Khan because he had boasted about his prior drug trafficking activities;

by his own admission, he was incarcerated for drug trafficking for seven years in

Dubai on prior drug trafficking charges; he had been added to OFAC’s list of

“specially designated” narcotics traffickers; and he had been able to procure high-

quality heroin in a war-torn country on short notice. The district court concluded

that “whether or not there was some element of puffery in it, it’s clear that [he was]

an experienced drug trafficker and that’s what [he was] prepared to do in this

case.” App’x 241.

Second, contrary to Khan’s argument, the district court took Khan’s age and

medical history into account. The district court noted that even the mandatory

12 minimum sentence of 10 years’ imprisonment was “itself a very serious sentence

and no less so for a man who is 71 years old”; that his age was “a significant

mitigating circumstance,” as was “the fact that he is in a foreign country with a

limited ability to communicate in English”; and that Khan was assessed to be in

“relative[ly] good health.” App’x 240-41, 243. Moreover, his argument that the

district court did not consider his risk of contracting Covid-19 in prison at

sentencing fails because it would have been impossible for the district court to

consider a concern that had not yet arisen when Khan was sentenced.

Because the district court carefully considered the § 3553(a) factors in

imposing Khan’s sentence, Khan has no basis to argue that his below-guidelines

sentence was “shockingly high, shockingly low, or otherwise unsupportable as a

matter of law.” United States v. Rigas,

(2d Cir. 2009).

* * *

We have considered Khan’s remaining arguments, which we conclude are

without merit. For the aforementioned reasons, we AFFIRM the judgment of the

district court.

FOR THE COURT: Catherine O’Hagan Wolfe, Clerk of Court

13