United States v. Timewell ( 2009 )


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  • 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