United States v. Timewell

No. 07-4587-cr
United States v. Timewell

UNITED STATES COURT OF APPEALS
FOR THE SECOND CIRCUIT

August Term 2008

Docket No. 07-4587-cr

Argued: November 18, 2008 Decided: June 1, 2009

UNITED STATES OF AMERICA,

Appellee,

v.
STEPHEN ANTHONY MARC JOHNSON, PATRICK BOWLER,

Defendants,

GREGORY PAUL TIMEWELL,

Defendant-Appellant.

Before: MINER, RAGGI, and LIVINGSTON, Circuit Judges.

Appeal from an order entered in the United States District
Court for the Eastern District of New York (Platt, J.) denying
the application of defendant-appellant to be resentenced
following a remand for further proceedings in conformity with
United States v. Crosby, 397 F.3d 103 (2d Cir. 2005), the
district court having taken into account, inter alia, the
government’s deviation from a customary practice of rescinding
cooperation agreements breached by defendants.
Order vacated and case remanded with instructions.

Burton T. Ryan Jr., Assistant
United States Attorney (Benton J.
Campbell, United States Attorney
for the Eastern District of New
York, Peter A. Norling, Assistant
United States Attorney, on the
brief), Brooklyn, New York, for
Appellee.

Ivan S. Fisher, New York, New York,
for Defendant-Appellant.

1
MINER, Circuit Judge:

Defendant-appellant Gregory Timewell appeals from a

Memorandum and Order entered on October 4, 2007, in the United

States District Court for the Eastern District of New York

(Platt, J.) denying his application to be resentenced following a

remand for further proceedings in conformity with United States

v. Crosby, 397 F.3d 103 (2d Cir. 2005). United States v.

Timewell, 124 F. App’x 55 (2d Cir. 2005). Timewell was

convicted, upon a guilty plea, of conspiracy to import 1,000
kilograms or more of hashish and marijuana, in violation of 21

U.S.C. §§ 960(a)(1), (b)(1)(G), 963, and of making false

statements to federal agents in violation of 18 U.S.C. § 1001.

On March 5, 2004, he was sentenced principally to a prison term

of 275 months and a 5-year term of supervised release. In the

Memorandum and Order determining that it would adhere to the

sentence originally imposed, the District Court took into

account, inter alia, the government’s customary practice of

rescinding cooperation agreements breached by defendants. For
the reasons that follow, we vacate the sentence and once more

remand for further proceedings.
BACKGROUND

I. Of the Events Leading to the Guilty Plea

Timewell, a native of New Zealand, was engaged as an

international distributor and smuggler of drugs over a period of

many years. He began his career as a local distributor of

marijuana in Australia and New Zealand and expanded his interests

2
to become a financier and organizer of worldwide smuggling

operations. His successful efforts in distributing tons of

hashish and marijuana in the United States and elsewhere enabled

him to accumulate millions of dollars in personal assets.

The specific enterprise giving rise to the prosecution

leading to this appeal was an undertaking by Timewell, along with

co-defendants Patrick Bowler and Stephen Johnson, to smuggle 25

tons of hashish through New York for distribution in Upstate New

York and Canada. Efforts to accomplish this goal occurred

between 1993 and 1995, but the goal never was realized. The

enterprise was infiltrated by undercover agents of the Drug

Enforcement Administration (“DEA”). One undercover agent was

recruited as a ship’s captain to off-load the hashish from a

“mother ship” in the Mid-Atlantic and to smuggle the drugs into

Long Island, New York. The agent was to be paid $75,000 to cover

his expenses for the trans-shipping, arrangements for payment

having been made by Timewell through co-conspirator Johnson.

Before the offloading could take place, the “mother ship,”
sailing from Pakistan under the direction of co-conspirator

Bowler, sustained mechanical failure. The ship was rerouted, and

its load of drugs ultimately was smuggled into Portugal and

Ireland. Timewell and Johnson were arrested in Canada in 1995.

Timewell subsequently waived extradition to the United States.

Timewell was indicted in the Eastern District of New York

for operating a continuing criminal enterprise, conspiracy to

import 1,000 kilograms or more of hashish and marijuana into the

3
United States and conspiracy to distribute 1,000 kilograms or

more of hashish and marijuana. The indictment included a demand

for forfeiture of “[o]ne [h]undred [m]illion [d]ollars

($100,000,000) in United States currency and property

constituting the proceeds of and derived from, directly and

indirectly, the foregoing offenses.” Timewell early on

manifested a desire to cooperate with the government. Upon his

arrival in the United States, he was extensively debriefed by

agents of the DEA as well as officials of foreign governments.
He provided information to them about his own criminal conduct

and assets and shared with them his knowledge regarding the

activities of the co-conspirators with whom he associated in the

United States and throughout the world.

In a Cooperation Agreement dated February 5, 1998, Timewell

agreed, inter alia, to plead guilty to conspiracy to import

hashish into the United States and further agreed to provide

truthful, complete, and accurate information to the Office of the

United States Attorney for the Eastern District of New York.
Timewell also agreed to testify at any proceedings, regardless of

location, when requested to do so by the Office and to make full

and complete financial disclosure. The Agreement identified

numerous assets belonging to Timewell, consisting of bank

accounts as well as real estate and currency in various countries

throughout the world, all of which he agreed to forfeit to the

government. For its part, the government agreed, inter alia, to

“file a motion pursuant to Guidelines Manual § 5K1.1 and 18

4
U.S.C. § 3553(e) with the sentencing [c]ourt setting forth the

nature and extent of [Timewell’s] cooperation,” thereby enabling

the court to impose a sentence below the Guidelines range and

below any applicable mandatory sentence, and “not [to] oppose a

downward adjustment of three levels for acceptance of

responsibility under Guidelines Manual § 3E1.1.” The Agreement

provided that, as determined by the United States Attorney’s

Office, if Timewell “intentionally violated any provision of

th[e] agreement, [he would] not be released from his plea of
guilty but th[e] Office [would] be released from its obligation .

. . (a) not to oppose a downward adjustment of three levels for

acceptance of responsibility . . ., and (b) to file the motion

described” relating to the nature and extent of Timewell’s

cooperation. Timewell pleaded guilty to the conspiracy charge on

February 5, 1998.

Timewell entered into a Supplemental Plea Agreement with the

United States Attorney dated March 1, 2001, in which he agreed to

waive indictment and plead guilty to a superseding information
charging him with making a false statement to federal officers in

violation of 18 U.S.C. § 1001. This charge was occasioned by the

discovery that Timewell had misled agents regarding more than

$4.8 million in Swiss francs that he had concealed in

Switzerland. The discovery came about through continuing

investigations relating to the arrests of Timewell’s co-

conspirators, including Bowler, who was arrested in Switzerland.

Confronted with his failure to reveal these drug proceeds,

5
Timewell arranged through his counsel to surrender to the

government $2,089,000 in Swiss francs, that amount being the

remainder of the proceeds. Timewell’s story was that he

originally believed that the funds in question had been removed

by Bowler or those acting for Bowler. He later learned that Jim

Wilson, a Canadian friend, had obtained the money and was sending

monthly payments to Timewell’s family. Timewell failed to notify

the government of these developments and thereby violated the

terms of his Cooperation Agreement. It is not contested by the
government that Timewell otherwise provided extensive and

substantial assistance to the government in identifying and

describing the international narcotics operation of numerous

individuals, including Bowler, Thomas Sherrett, and Michael

Vondette, Timewell having testified as a witness at the trial of

Vondette. See United States v. Vondette, 248 F. Supp. 2d 149,

164 (E.D.N.Y. 2001).

II. Of the Sentencing

The pre-sentence report recommended a total offense level of
41. Starting with the base level of 38, predicated upon 120,975

kilograms of marijuana, see U.S.S.G. § 2D1.1(a)(3), four levels

were added for leadership role, see U.S.S.G. § 3B1.1(a), and two

levels were added for obstruction of justice in the concealment

of assets, see U.S.S.G. § 3C1.1. From the 44 levels thus arrived

at was subtracted 3 levels for acceptance of responsibility, see

U.S.S.G. § 3E1.1, with level 41 as the final result. Applying

Criminal History Category I as recommended, the Guidelines

6
Sentencing range was 324-405 months of incarceration. Prior to

sentencing, the government submitted pursuant to U.S.S.G. § 5K1.1

a letter dated March 4, 2004, setting forth the basis for its

recommendation that “the Court grant a significant downward

departure in formulating Timewell’s sentence.” The letter,

signed by an Assistant United States Attorney for the Eastern

District of New York, described in detail Timewell’s extensive

cooperation with the authorities and noted that the information

provided “was detailed, corroborated and consistently aided the
agents in developing their investigation.” According to the

letter, Timewell’s substantial assistance “resulted in the arrest

and conviction of major drug violators and the seizure of

millions of dollars in drug proceeds.”

Timewell was sentenced on March 5, 2004. During the

sentencing proceeding, Timewell’s counsel, urging a substantial

Guidelines reduction, recounted at length Timewell’s extensive

cooperation, assistance to various law enforcement authorities,

and testimony provided at the trial of Vondette. Before imposing
sentence, the court noted that Timewell had not fully cooperated

and therefore was in violation of the Cooperation Agreement.

Counsel for Timewell pointed out that the pre-sentence

calculation accounted for that by including a two-level upward

adjustment for obstruction of justice. The court responded:

I saw that. But it doesn’t affect the
[G]uidelines as such, the [G]uideline computation.

As I said in 99 percent of the cases where this
happens the government says you don’t get any
cooperation letter by breaching your opportunity to
7
 cooperate fully. And that’s a fact I had to take into
consideration in this case with respect to other
features.

The court then observed that, according to the pre-sentence

report,

information received from the government indicates that
between January 1993 and May 1995 Timewell and others
conspired to import and distribute 22,000 kilograms of
hashish into the United States via Pakistan. This has
been going on for many, many years.

. . . .

The volume is staggering of what [Timewell] did.
It’s mind boggling, with the exception of Vondette. It
is one of the biggest I have ever come across in my 30
years here.

The court further observed:

The money involved in addition to the drug
quantities [is] mind boggling. It is to me, maybe not
to other people: But it is an enormous amount of money
involved.

Were it not for the government’s letter I would
have had no hesitancy in imposing 405 months, the upper
end of the [G]uidelines and departing upward.

. . . .

So I will depart down effectively from the 405
months, and that’s to the minimum of 275 months.
The court also imposed a term of imprisonment of 60 months on the

false statement count, to be served concurrently. A timely

appeal followed.

III. Of the Initial Appeal

On his initial appeal, Timewell

assert[ed] that (1) his sentence [was] unconstitutional
because it [was] premised on facts not proved beyond a
reasonable doubt to the jury as required by the Sixth
Amendment, see Blakely v. Washington, 542 U.S. 296
(2004); and (2) the district court erred in granting a
8
 § 5K1.1 departure from the guidelines because (a) it
mistakenly thought defendant’s guidelines were not
affected by his § 1001 conviction, and (b) it was
improperly influenced by the United States Attorney’s
Office’s policy of not making specific sentencing
recommendations in connection with its § 5K1.1 motions.

United States v. Timewell, 124 F. App’x 55, 56 (2d Cir. 2005).

We rejected these arguments, holding that downward departure from

the Sentencing Guidelines generally is not reviewable on appeal,

id.; that even if the District Court erred in misapprehending the

effect of the § 1001 conviction on the Guidelines calculations (a
fact of which we were not convinced), it was not mistaken that

the false statements had obstructed justice and therefore

properly considered that fact in determining the extent of

departure, id. at 57; and that there was no abdication of

judicial responsibility, since the District Court carefully

considered the parties’ submissions as well as the facts outlined

in the pre-sentence report, id. As to Timewell’s claim that the

Guidelines-determined sentence was imposed in violation of his

Sixth Amendment rights, we made the following determination: “In

light of the Supreme Court’s decision in United States v. Booker,
543 U.S. 220 (2005), and this court’s decision in United States

v. Crosby, 397 F.3d 103 (2d Cir. 2005), this case is remanded to

the district court for further proceedings in conformity with

Crosby.” Id. at 57-58.

IV. Of the Proceedings on the Crosby Remand

Seeking on remand “a post-Booker sentence significantly

lower than the 275-month term of imprisonment handed down on

9
March 5, 2004,” Timewell’s attorney submitted to the court a

letter dated July 11, 2005, arguing that Timewell’s original

sentence was “keyed to the mandatory Guidelines then in place”

and urging a sentence taking into account “the factors . . . set

out in 18 U.S.C. § 3553(a).” In the letter, Counsel recounted

the extensive cooperation provided by his client to the

authorities and again explained Timewell’s failure to disclose

his knowledge of the transfer of the $5 million Swiss bank

account. Counsel took special note of the sentence imposed upon

co-conspirator Sherrett, whose original sentence of 188 months

(which took into account a three-level downward departure for

assisting a prison guard attacked by inmates) was reduced to 120

months for cooperation, which included testimony at the trials of

Vondette. Counsel’s letter concluded as follows:

I urge Your Honor to reflect carefully about an error
you may have made with regard to the Guidelines
computation relating to the 18 U.S.C. § 1001 conduct,
to consider the 10-year sentence you imposed on co-
defendant Thomas Sherrett, and to consider the
government’s functional equivalent of its highest
recommendation of Timewell as the best of 146
cooperators in this case.
The government’s submission on remand consisted of a letter

dated July 7, 2005, signed by Assistant United States Attorney

Burton T. Ryan Jr. The letter included a brief review of the

history of the case and a description of the purpose of a Crosby

remand as well as the procedure to be followed on such a remand.

Noting that the government’s 5K1.1 letter enabled the court to

depart from the Guidelines and impose a sentence of 275 months,

10
the letter concluded as follows:

[O]nly the Court can determine to what extent the then
mandatory nature of the Guidelines [a]ffected the
sentence the Court imposed. The question of whether
the sentence would have . . . been materially different
if the guidelines were only advisory, we leave . . . to
the Court’s discretion.

An additional submission came in the form of a letter dated

July 1, 2005, from David S. Katz, President and CEO of Global

Security Group, Inc. Katz was a former Special Agent of the Drug

Enforcement Administration and was the Agent charged with
debriefing Timewell. In his 8-page letter to the court, Katz

detailed the extensive information he gleaned from Timewell’s

cooperation during the period 1996-1998. According to Katz, the

overwhelming majority of information provided by Timewell was

previously unknown to the government and would never have been

known without Timewell’s cooperation. Katz characterized

Timewell as “an extremely valuable source of information that

furthered the investigation [he] had been conducting.” Katz

noted that the international drug trafficking information

provided not only furthered his own investigation but “was also
provided to the law enforcement authorities of Canada,

Switzerland, Australia, Thailand, Belgium, Pakistan, Singapore,

Spain, Portugal, the Netherlands, Ireland and the United

Kingdom.”

In a letter submission dated September 10, 2007, counsel for

Timewell noted that Timewell’s cooperation was much more

extensive than that of Sherrett. Counsel also noted that

11
Assistant United States Attorney Ryan had commented as follows in

comparing the sentences of Timewell and Sherrett: “While their

roles were similar, the amounts of the drugs Mr. [Sherrett] was

held accountable for were much less.” (alteration in original;

emphasis omitted).

The proceedings on remand concluded with extensive arguments

by counsel and colloquies with the court on September 20, 2007.

Counsel for Timewell argued that co-conspirators more culpable

than Timewell received more lenient sentences, with special
references to co-conspirators Sherrett and Johnson. Although

Johnson was sentenced after this Court ordered Timewell’s Crosby

remand, the government had consented to an adjournment of

Timewell’s Crosby hearing to permit consideration of Johnson’s

sentence, which was to a term of incarceration of fifteen years

(180 months).

At the hearing, Assistant United States Attorney Kelly

advised the court that Timewell may have been put in a situation

worse than Johnson because of his extensive disclosures. He
noted that dealing with Johnson’s proffers was like “pulling

teeth” and that Johnson was in no way as forthcoming as Timewell.

Johnson did not receive a letter recommending consideration for

his cooperation. Kelly referred to the “good faith” of Timewell

and made this statement: “And so we ask the [c]ourt to give

serious consideration and weight to the argument that there

should not be a significant disparity between Mr. Johnston [sic]

and Mr. Timewell.”

12
 Despite the urging of the government, the District Court was

concerned that Timewell failed to disclose the account in

Switzerland and therefore, in accordance with past practices in

the United States Attorney’s Office, should not have had the

benefit of the cooperation letter supplied by the government:

Well, mainly my understanding of . . . this case,
probably, and the principle that the U.S. Attorney’s
Office in this district — which is unique as far as any
district is concerned in this country as far as I can
determine — if you didn’t cooperate properly, and you
violated your agreement with the government and didn’t
give full and accurate descriptions of everything, you
lose all your benefits. Not just a partial, or not
just some of it, but all benefits in the cooperation
letter.

Now, when you hide 2 and-a-half million dollars in
drug money in Switzerland, and it comes out through
other sources than the defendant — what happened to
that rule?

Assistant United States Attorney Kelly, to whom the court’s

remarks were addressed, responded that his Office decided “to

continue with the cooperation and penalize him by having him

plead to the false statement charge.” Mr. Kelly went on to

emphasize the importance of Timewell’s cooperation and the
resultant benefit to the government, specifically pointing out

the disparity in sentences between Timewell and Johnson and the

failure of Johnson, who did not receive a 5K1.1 letter, to make

full disclosure. The court persisted in expressing its concern:

[I]n several prior cases, the moment a defendant has
told the government a material falsehood, the
[G]uidelines go like hard rock rules in those days.
And there was no such thing as a reduction once he has
taken that position. And I think there was a universal
rule. I know it happened many times in this court.

Timewell’s counsel then stated that in his experience
13
“[t]here is no rule” that requires the government to “shred a

cooperation agreement” for failure to disclose assets. The court

responded: “There is no rule. But it has been invoked in this

[c]ourt more times than you can imagine.” In a later colloquy

with Timewell’s counsel in which counsel argued that the court

had erroneously referred to the government’s customary practice

as a rule, the court responded: “[T]hey said to me it was a

rule. And they have been representing that to me for years. . .

. Not my rule. I certainly don’t make up the rules.”
The District Court also discussed with the government the

sentencing range that would have applied to Timewell absent the

submission of a 5K1.1 letter. Mr. Kelly indicated that Timewell

“was at [an offense level of] 45 at one point,” which carried a

minimum sentence of life imprisonment. The District Court

appeared to accept this summary of the applicable Guidelines

calculation, suggesting that Timewell had benefitted

substantially from his cooperation since he received a sentence

of only 275 months. In fact, however, and as previously noted,
Timewell’s actual Guidelines sentencing range was 324 to 405

months, not life imprisonment as represented by the government.

V. Of the Decision on Remand

By Memorandum and Order entered on October 4, 2007, the

District Court issued its decision on remand. Classifying the

matter before it as a motion to reconsider its 275-month

sentence, the court noted that counsel had advanced a claim of

unwarranted disparities. According to the District Court,

14
Timewell’s counsel put forth the names of four defendants for

comparison as similarly situated to Timewell: Michael Vondette,

Mark Johnson, Patrick Bowler and Thomas Sherrett. The court

reviewed the sentences imposed upon these co-defendants and the

quantities of marijuana for which they were held responsible and

found that Timewell was in a position different from the others:

The major factor in the difference between
Timewell and three other defendants — Johnson, Bowler
and Sherrett — was and is the fact that Timewell
violated his plea agreement with the government by
failing to reveal five million dollars ($5,000,000) in
drug proceeds that he had concealed in Europe. When
confronted with this fact, he revealed only $2,890,000
[sic], i.e., leaving about $2,000,000 for which there
has been no account.

In view of the foregoing facts, the court justified its

disparate treatment of Timewell as follows:

In innumerable cases (notwithstanding counsel for
Timewell’s claim to the contrary) that have come before
this [c]ourt, the Government has advised that when a
defendant violates his plea agreement with the
Government, the agreement is voided. This Court took
that into account in substantially increasing
Timewell’s sentence from what it otherwise would have
been.

(emphasis supplied). Accordingly, the court denied Timewell’s
motion and this appeal followed. On appeal, Timewell argues that

the District Court decision was procedurally as well as

substantively unreasonable. He also requests that any remand of

his case be to a different judge for sentencing.
ANALYSIS

A. Of the District Court’s Mandate on Remand

Following the Supreme Court’s determination in United States

v. Booker, 543 U.S. 220 (2005), that the Sentencing Guidelines
15
were to be considered advisory and not mandatory, this Court

formulated the rule in Crosby for plain error review of pre-

Booker sentences. See United States v. Garcia, 413 F.3d 201,

224–26 (2d Cir. 2005) (discussing rationale and procedure for

Crosby remand). Concluding that such a review requires a

resolution of the issue of whether the sentence originally

imposed is materially different from the sentence that would have

been imposed under the Booker regime, we formulated the protocol

now known as the Crosby remand to enable the District Court to
decide the issue in the first instance. On such remand, District

Judges are to re-examine sentences in light of the following:

[A]ny of the errors in the procedure for selecting the
original sentence . . . would be harmless, and not
prejudicial under plain error analysis, if the judge
decides on remand, in full compliance with now
applicable requirements, that under the post-
Booker/Fanfan regime the sentence would have been
essentially the same as originally imposed.
Conversely, a district judge’s decision that the
original sentence would have differed in a nontrivial
manner from that imposed will demonstrate that the
error in imposing the original sentence was harmful and
satisfies plain error analysis.

Crosby, 397 F.3d at 118.
Accordingly, the question to be resolved by the District

Court is “whether the challenged sentence is materially different

from the one that the district court would have imposed with a

correct understanding of federal sentencing law as now explained

by the Supreme Court.” Garcia, 413 F.3d at 224. If the District

Court decides not to resentence, it should explain that decision

on the record; if it decides that the sentence should be vacated,

it must resentence in accordance with Booker, with an
16
explanation. Crosby, 397 F.3d at 120. The explanation referred

to in Crosby is required by 18 U.S.C. § 3553(c), which provides

in part that “[t]he court, at the time of sentencing, shall state

in open court the reasons for its imposition of the particular

sentence.”

To sentence in compliance with Booker, the court is

constrained to consider the sentencing factors set out in 18

U.S.C. § 3553(a):

(1) the nature and circumstances of the offense and the
history and characteristics of the defendant;

(2) the need for the sentence imposed —

(A) to reflect the seriousness of the offense, to
promote respect for the law, and to provide just
punishment for the offense;

(B) to afford adequate deterrence to criminal
conduct;

(C) to protect the public from further crimes of
the defendant; and

(D) to provide the defendant with needed
educational or vocational training, medical care,
or other correctional treatment in the most
effective manner;
(3) the kinds of sentences available;

(4) the kinds of sentence and the sentencing range
established for —

(A) the applicable category of offense committed
by the applicable category of defendant as set
forth in the guidelines . . . issued by the
Sentencing Commission pursuant to [28 U.S.C. §
994(a)(1)] . . .

. . . .

(5) any pertinent policy statement — (A) issued by the
Sentencing Commission pursuant to [28 U.S.C. §
994(a)(2)] . . .;
17
 (6) the need to avoid unwarranted sentence disparities
among defendants with similar records who have been
found guilty of similar conduct; and

(7) the need to provide restitution to any victims of
the offense.

However, all sentencing proceedings must commence with the

District Court’s calculation of the applicable Guidelines range,

with the Guidelines as “the starting point and the initial

benchmark.” Gall v. United States, 128 S. Ct. 586, 596 (2007).

The court must then consider all the § 3553(a) factors and then
undertake “an individualized assessment based on the facts

presented.” Id. at 597. If a non-Guidelines sentence is

indicated, the court “must consider the extent of the deviation

[from the Guidelines] and ensure that the justification is

sufficiently compelling to support the degree of the variance.”

Id. Finally, “[a]fter settling on the appropriate sentence, [the

District Court] must adequately explain the chosen sentence to

allow for meaningful appellate review and to promote the

perception of fair sentencing.” Id. (citation omitted).

B. Of the Standards of Review
Following Booker, we are constrained to review sentences for

reasonableness. See Booker, 543 U.S. at 260–61; see also United

States v. Fernandez, 443 F.3d 19, 26–27 (2006). Reasonableness

review requires an examination of the length of the sentence

(substantive reasonableness) as well as the procedure employed in

arriving at the sentence (procedural reasonableness). See United

States v. Canova, 485 F.3d 674, 679 (2d Cir. 2007). In our

review of district court sentences, we are required to apply a
18
“deferential abuse-of-discretion standard.” Gall, 128 S. Ct. at

591. We recently stated that “[a]s to substance, we will not

substitute our own judgment for the district court’s on the

question of what is sufficient to meet the § 3553(a)

considerations in any particular case” and that the substantive

determination of a District Court will be set aside only in those

special cases where the range of permissible decisions does not

encompass the District Court’s determination. See United States

v. Cavera, 550 F.3d 180, 189 (2d Cir. 2008) (en banc).
Accordingly, “when conducting substantive review, we take into

account the totality of the circumstances, giving due deference

to the sentencing judge’s exercise of discretion, and bearing in

mind the institutional advantages of district courts.” Id. at

190.

However, the deference due the district court in sentencing

requires that we first be satisfied that the procedural

requirements for sentencing have been satisfied. Id. at 189.

Procedural error occurs when the district court (1) fails to
calculate the Guidelines range; (2) is mistaken in the Guidelines

calculation; (3) treats the Guidelines as mandatory; (4) does not

give proper consideration to the § 3553(a) factors; (5) makes

clearly erroneous factual findings; (6) does not adequately

explain the sentence imposed; or (7) deviates from the Guidelines

range without explanation. Id. at 190. We have noted that a

sentence is procedurally unreasonable if a district court

“committed an error of law in the course of exercising

19
discretion,” Crosby, 397 F.3d at 114 (emphasis supplied), erred

“in determining the applicable Guideline range or the

availability of departure authority,” United States v.

Selioutsky, 409 F.3d 114, 118 (2d Cir. 2005) (emphasis supplied),

or misapprehended its ability to impose a non-Guidelines

sentence, see United States v. Sanchez, 517 F.3d 651, 661-62 (2d

Cir. 2008). Our identification of significant procedural error

may be a cause for remanding to the district court for

explanation or correction. Cavera, 550 F.3d at 190.
We undertake a reasonableness review “even after a District

Court declines to resentence pursuant to Crosby.” United States

v. Williams, 475 F.3d 468, 474 (2d Cir. 2007). Such a review is

precluded, however, where (1) the court determines that the

discharge of its obligations under post-Booker procedures,

treating the Guidelines as advisory only, would not result in a

sentence materially different from the sentence imposed under the

mandatory Guidelines procedure; or (2) the law of the case

doctrine applies to bar challenges to sentencing rulings that
were, or could have been, adjudicated in the initial appeal. Id.

at 475. “The law of the case doctrine will not, however, bar a

defendant who is not resentenced after a Crosby remand from

challenging the procedures used by the district court during the

Crosby remand,” and one not resentenced may therefore

“challeng[e] the manner in which the district court conducted the

Crosby remand.” Id. at 476.

C. Of the District Court’s Procedural Errors

20
 On a Crosby remand, the district court must determine

whether its sentence under the Booker regime would have been

materially different from the sentence originally imposed; if the

answer is “yes,” nothing further is required; if the answer is

“no,” there must be a resentencing. See United States v.

Ferrell, 485 F.3d 687, 688-89 (2d Cir. 2007). The District Court

here did not respond directly to the required inquiry. Indeed,

the court and counsel immediately began to discuss whether a more

lenient sentence should be imposed in light of the sentencing
disparities identified by counsel. This was procedural error

because “[o]nly if the district court answers the threshold

[Crosby] determination in the affirmative does a resentencing

occur.” Id.

We are unable to conclude that the District Court’s Crosby

error was harmless. See United States v. Williams, 524 F.3d 209,

214 (2d Cir. 2008) (recognizing that procedural error at

sentencing can be reviewed for harmlessness). First, the

District Court adhered to its original sentence after it “took
. . . into account” what the court perceived to be the

government’s customary practice of voiding plea agreements where

a defendant violates the terms of the agreement. That such a

customary practice exists is unsupported by the record before the

District Court. See Cavera, 550 F.3d at 190 (noting that a

district court commits procedural error when it “rests its

sentence on a clearly erroneous finding of fact”).

Second, although a district court alone may determine what

21
effect to give to a 5K1.1 letter, in so doing may consider the

extent of downward departures or variances received by other

similarly situated defendants who have cooperated, and may even

decline a reduction from the Guidelines altogether, the court

here erred in the course of exercising its discretion by (1)

“substantially increasing Timewell’s sentence from what it

otherwise would have been” and (2) giving as a reason for the

increase the government’s failure to comply with the purported

customary prosecutorial practice of voiding cooperation
agreements upon breach by the defendant. The 5K1.1 letter, which

the government saw fit not to revoke in Timewell’s case despite

his breach of the cooperation agreement, allows a downward

departure from the Sentencing Guidelines in cases where a

defendant provides substantial assistance to the government.

Whether such a letter is merited is confided to the sole

determination of the government, subject only to constitutional

limitations. See Wade v. United States, 504 U.S. 181, 185–86

(1992). That the government usually voids cooperation agreements
upon a breach by the defendant should not be reason to constrain

a district court from giving proper effect to a 5K1.1 letter if

the government decides to submit a 5K1.1 letter notwithstanding

the defendant’s breach of the cooperation agreement.

In addition, the government indicated, and the District

Court appeared to accept, that, absent a downward departure for

substantial cooperation, the Guidelines would have recommended

that Timewell serve a life sentence. As previously discussed,

22
however, the pre-sentence report, to which the District Court

adhered when calculating the Guidelines recommendation at

Timewell’s initial sentencing, established a total offense level

of 41 carrying a sentencing range of only 324 to 405 months. The

description of the sentencing range to which Timewell would have

been subject absent his substantial cooperation therefore

substantially overstated Timewell’s actual Guidelines range. See

Cavera, 550 F.3d at 190 (indicating that a District Court errs

when it “makes a mistake in its Guidelines calculation”).
Because we cannot determine the extent to which these errors

affected the District Court’s analysis, we are unable to discern

how the District Court would have answered the threshold Crosby

question in the absence of these errors. See Crosby, 397 F.3d at

115 (noting that procedural error is “cause for concern because,

in many cases, it will be impossible to tell whether the judge

would have imposed the same sentence had the judge not felt

compelled to impose a Guidelines sentence”).

The District Court also erred in its written opinion by
mischaracterizing the unwarranted disparities argument made by

defense counsel. The District Court wrote that counsel for

Timewell argued that Timewell received a disparate sentence as

compared to Michael Vondette, Stephen Johnson, Patrick Bowler,

and Thomas Sherrett. However, Timewell’s application listed only

Sherrett and Johnson as comparators. Indeed, a determination of

whether to be resentenced on a Crosby remand must be based only

on the circumstances existing at the time of the original

23
sentence. See Ferrell, 485 F.3d at 688; Crosby, 397 F.3d at 118,

n.19. Under this rule, the court could not, in the course of its

threshold Crosby analysis, consider the sentence of Bowler or

Johnson, both of which were imposed after Timewell’s original

sentence was pronounced. Notably, the District Court also erred

in stating that Johnson “testified against Vondette in this

Court.”

Accordingly, we find that the District Court erred in

neglecting to answer the question posed by the Crosby remand of

Timewell’s original sentence, namely, whether, based on the

circumstances at the time of the original sentence, the District

Court would have imposed a materially different sentence under

the post-Booker sentencing regime, and that this error was not

harmless. See Crosby, 397 F.3d at 118. The law of the case does

not bar Timewell from challenging the manner in which the Crosby

remand was conducted despite the Court’s adherence to the

original sentence. We are therefore constrained to remand the

case once more to enable the District Court to formulate a proper
response to the Crosby inquiry. The District Court should state

the reasons for the response without consideration of past

practices of the government in regard to the rescission of

cooperation agreements. Such consideration was error. Should

the court determine to revisit its original sentence, we ask it

to consider: (1) that a district court may — but is not required

to — consider sentencing disparity among co-defendants under 18

U.S.C § 3553(a)(6); United States v. Frias, 521 F.3d 229, 236 n.8

24
(2d Cir. 2008); (2) that the United States Attorney’s Office

recommended a “substantial” departure from the Guidelines

sentence in view of Timewell’s excellent cooperation and asserted

that a significant disparity in the sentences imposed upon

Timewell, Johnson and Sherrett was not warranted; (3) that the

appropriateness of any reduction of sentence below the Guidelines

should be governed by the provisions set out in U.S.S.G. § 5K1.1:

(a) The appropriate reduction shall be determined by
the court for reasons stated that may include, but are
not limited to, consideration of the following:
(1) the court’s evaluation of the significance
and usefulness of the defendant’s assistance,
taking into consideration the government’s
evaluation of the assistance rendered;

(2) the truthfulness, completeness, and
reliability of any information or testimony
provided by the defendant;

(3) the nature and extent of the defendant’s
assistance;

(4) any injury suffered, or any danger or risk of
injury to the defendant or his family
resulting from his assistance;

(5) the timeliness of the defendant’s assistance.
In the absence of a showing of any unfairness or the

appearance of any unfairness on the part of the District Judge,

we reject Timewell’s claim that the case should be reassigned to

another judge on remand. See United States v. Bradley, 812 F.2d

774, 782 n.9 (2d Cir. 1987).
CONCLUSION

This case is remanded to the District Court for further

proceedings consistent with the foregoing.

25