United States v. Powell ( 2001 )


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  •                                                                                                                            Opinions of the United
    2001 Decisions                                                                                                             States Court of Appeals
    for the Third Circuit
    10-16-2001
    USA v. Powell
    Precedential or Non-Precedential:
    Docket 00-2440
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    http://digitalcommons.law.villanova.edu/thirdcircuit_2001/239
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    Filed October 16, 2001
    UNITED STATES COURT OF APPEALS
    FOR THE THIRD CIRCUIT
    No. 00-2440
    UNITED STATES OF AMERICA,
    v.
    ALLEN POWELL, a/k/a KEITH BATES
    ALLEN POWELL,
    Appellant
    Appeal from United States District Court
    for the Eastern District of Pennsylvania
    Docket No. 99-cr-00719
    District Judge: Honorable Eduardo C. Robreno
    Argued March 9, 2001
    Before: BECKER, McKEE and STAPLETON, Circuit Judges
    (Opinion Filed: October 16, 2001)
    Maureen Kearney Rowley, Esq.
    Chief Federal Defender
    David L. McColgin, Esq. (Argued)
    Elaine DeMasse, Esq.
    Assistant Federal Defender
    Supervising Appellate Attorney
    Federal Court Division
    Defender Association of Philadelphia
    Suite 540 West -- The Curtis Center
    Independence Square West
    Philadelphia, PA 19106
    Attorney for Appellant
    Michael R. Stiles
    United States Attorney
    Walter S. Batty, Jr.
    Assistant United States Attorney
    Chief of Appeals
    Kathleen M. Rice (Argued)
    Assistant United States Attorney
    Suite 1250 615 Chestnut Street
    Philadelphia, Pennsylvania 19106
    Attorney for Appellee
    Mitchell E. Zamoff, Esq.
    Hogan & Hartson
    555 13th Street, N.W.
    Washington, D.C. 20004-1109
    Attorney for Appellee
    OPINION OF THE COURT
    McKEE, Circuit Judge:
    Allen Powell appeals his sentence of 192 months of
    imprisonment followed by five years supervised release. He
    argues that the district court erred by not ruling on his pro
    se motion for a downward departure based upon conditions
    of confinement, and by imposing a period of supervised
    release that was longer than explained in his plea
    agreement and the change of plea colloquy.
    For the reasons that follow, we will vacate the sentence
    and remand to the district court for clarification of its
    rationale for denying his motion for a downward departure.
    Our remand will also allow the district court to consider a
    concession regarding the supervised release that the
    government has made during the course of this appeal.
    I. Background
    On November 9, 1999, a grand jury charged Powell with
    one count of possession of a firearm by a convicted felon in
    violation of 18 U.S.C. S 922(g)(1). On December 15, 1999,
    the government filed a notice of prior convictions statement
    2
    pursuant to 18 U.S.C. S 1924(e).1 Thereafter, Powell entered
    into a written plea agreement. In that agreement, the
    government stipulated that his "offense level is 33,
    pursuant to U.S.S.G. Section 4B1.4, because he is an
    armed career criminal," and that Powell was eligible for a
    three-point downward departure for acceptance of
    responsibility pursuant to U.S.S.G. SS 3E1.1(a) & (b). App.
    at 129a-30a. The government also agreed to "[m]ake
    whatever sentencing recommendation as to imprisonment,
    fines, forfeiture, restitution and other matters which the
    government deems appropriate." 
    Id. at 127a.
    The plea
    agreement also stated:
    [Powell] has the three prior convictions set forth in the
    Notice of Defendant's Prior Convictions for Enhanced
    Sentencing Under Title 18, United States Code, Section
    924(e) filed by the government in this action. Therefore,
    the defendant understands, agrees and has had
    explained to him by counsel that the Court may impose
    the following maximum sentence; Life imprisonment--
    with a 15-year mandatory minimum term of
    imprisonment -- a $250,000 fine, a three-year term of
    supervised release and a $100 special assessment. . .
    The defendant may not withdraw his plea because the
    Court declines to follow any recommendation, motion
    or stipulation by the parties to this agreement. No one
    has promised or guaranteed to the defendant what
    sentence the Court will impose.
    
    Id. at 127-28
    (emphasis added). The agreement further
    _________________________________________________________________
    1. Section 924 is entitled "Penalties," and states:
    (e)(1) In the case of a person who violates section 922(g) of this
    title
    and has three previous convictions by any court referred to in
    section 922(g)(1) of this title for a violent felony or a serious
    drug
    offense, or both, committed on occasions different from one
    another,
    such person shall be fined not more than $25,000 and imprisoned
    not less than fifteen years. . . .
    18 U.S.C. S 924(e). Section 924(e), which does not expressly delineate a
    maximum term of imprisonment, has been construed to allow a life
    sentence. United States v. Mack, 
    229 F.3d 226
    , 229 n.4 (3d Cir. 2000)
    (citing Custis v. United States, 
    511 U.S. 485
    (1994)).
    3
    provided that the stipulations did not bind the court and
    that the court could make determinations that might
    increase or decrease the applicable range under the
    Sentencing Guidelines, and thereby affect Powell's
    sentence.
    At the ensuing change of plea hearing, the court asked
    the government to state the maximum penalty. The
    prosecutor responded as follows:
    The maximum penalties are life imprisonment, a
    $250,000.00 fine, a three-year term of supervised
    release and a $100.00 special assessment. There is a
    fifteen-year mandatory minimum prison sentence,
    which is applicable to this case.
    THE COURT: Mr. Powell, do you understand the
    maximum penalty to be just as stated by the Assistant
    United States Attorney?
    THE DEFENDANT: Yes.
    THE COURT: Has your attorney discussed with you the
    sentencing guidelines?
    THE DEFENDANT: Yes.
    THE COURT: Do you understand, the Court will not be
    able to determine how the sentencing guidelines will be
    applied in your case, until after the presentence
    investigation report is completed and you and the
    Government have had an opportunity to challenge the
    facts reported by the Probation Officer?
    DEFENDANT: Yes.
    ***
    ***
    THE COURT: Do you understand that the Court could
    in appropriate circumstances, impose a sentence which
    is more severe than the sentence, which the guidelines
    recommend?
    DEFENDANT: Yes.
    THE COURT: Do you understand that if you are sent to
    prison, a term of supervised release may be imposed
    when you are released from prison?
    4
    DEFENDANT: Yes.
    
    Id. 40a -
    42a (emphasis added). The court accepted the
    guilty plea and ordered a Pre-sentence Investigation.
    Thereafter, while in custody awaiting sentencing, Powell
    sent a letter to the district court complaining of what he
    characterized as substandard conditions at the Hudson
    County Jail in New Jersey where he was being detained
    pending sentencing. He attached a list of those conditions,
    and argued that the conditions entitled him to a downward
    departure pursuant to United States v. Brinton , 
    139 F.3d 718
    (9th Cir. 1998).
    The Presentence Report that the court subsequently
    received stated that the maximum sentence was "life
    imprisonment, with a mandatory minimum of 15 years,
    pursuant to 18 U.S.C. S 924(e)." PSI atP 50. The sentencing
    range in the report was calculated between 180 to 210
    months of imprisonment.2 The PSI also stated "[i]f a term of
    imprisonment is imposed, the Court may impose a term of
    supervised release of not more than five years , pursuant to
    18 U.S.C. S 3583(b)(1)." PSI at P 53 (emphasis added).
    Defense counsel objected to the recommendations in the
    PSI based upon the Supreme Court's decision in Apprendi
    v. New Jersey, 
    530 U.S. 466
    , 
    120 S. Ct. 2348
    (2000). He
    argued that Powell should not be subjected to sentencing
    enhancements under 18 U.S.C. S 924(e) and U.S.S.G.
    S 4B1.4(b)(3)(B) because the indictment failed to allege the
    predicate convictions for those enhancements. Even though
    Powell had previously been informed that the maximum
    supervised release that could be imposed was three years,
    he neither questioned nor objected to the report's statement
    that the maximum term was five years.
    The district court concluded that the applicable
    sentencing range under the guidelines was 180 to 210
    months followed by a period of supervised release of three
    _________________________________________________________________
    2. The PSI stated "based on a total offense level of 30 and a criminal
    history category of VI, the guideline range for imprisonment is 168 to
    210 months. However, since the mandatory minimum term of
    imprisonment is 180 months, the effective guideline range is 180 to
    210 months." PSI at P 51 (emphasis in original).
    5
    to five years. Powell did not object. The court interpreted
    Powell's letter about the conditions at the Hudson County
    facility as a pro se motion for a downward departure based
    on the substandard conditions of his presentence
    detention. App. at 48a.
    The court rejected Powell's Apprendi claim, and
    sentenced Powell to 192 months of imprisonment (16 years)
    plus a five-year term of supervised release. The court
    imposed that sentence without ever formally ruling upon
    Powell's motion for a downward departure based upon the
    conditions of his presentence detention. This appeal
    followed.
    II. Jurisdiction, Issues & Standards of Review
    The district court had jurisdiction pursuant to 18 U.S.C.
    S 3231. We have appellate jurisdiction under 18 U.S.C.
    S 3742, and 28 U.S.C. S 1291. We must decide if the district
    court erred in failing to address Powell's request for a
    downward departure based on substandard conditions of
    confinement. "We review the district court's decisions
    concerning departures from the Sentencing Guidelines for
    abuse of discretion." United States v. Abuhouran, 
    161 F.3d 206
    , 209 (3d Cir. 1998). However, when reviewing legal
    questions regarding the application of the guidelines, "we
    need not defer to the district court's conclusion, and we will
    review its holding for legal error." 
    Id. Here, however,
    we do
    not know why the district court rejected Powell's request for
    a downward departure. The court merely announced that it
    would treat Powell's letter as a pro se motion for a
    departure, but sentenced Powell without departing from the
    applicable guideline range, and without explicitly ruling on
    Powell's pro se motion. For the purposes of this appeal, we
    will assume that the court's sentence to the suggested
    guideline range constituted an implicit denial of Powell's
    motion for a downward departure. In United States v.
    Mummert we explained our jurisdiction to review a district
    court's denial of a motion for departure. We stated:
    [I]f the ruling was based on the district court's belief
    that a departure was legally impermissible, we have
    jurisdiction to determine whether the district court's
    6
    understanding of the law was correct. By contrast, if
    the district court's ruling was based on an exercise of
    discretion, we lack jurisdiction [under United States v.
    Denardi, 
    892 F.2d 269
    , 271-72 (1989)].
    United States v. Mummert, 
    34 F.3d 201
    , 205 (3d Cir. 1994).
    We must also determine if Powell's guilty plea agreement
    included an understanding as to the supervised release he
    was exposed to and if so, whether he is entitled to specific
    performance of that portion of his plea agreement. 3 We
    review that claim for harmless error. Fed.R.Crim.P.11(h);4
    United States v. Electrodyne Systems Corp., 
    147 F.3d 250
    ,
    252 (3d Cir. 1998). Our review of whether the government
    violated the terms of the plea agreement is plenary as it is
    a question of law, and there is no factual dispute. United
    States v. Moscahlaidis, 
    868 F.3d 1357
    , 1360 (3d Cir. 1989).
    III. Discussion
    A. Powell's Pro Se Downward Departure Motion
    Inasmuch as the district sentenced Powell without ruling
    on his request for a downward departure, we have no way
    of knowing why the district court denied the requested
    departure. As noted above, under United States v. Denardi,
    
    892 F.2d 269
    , 271-72 (3rd Cir. 1989), if the court chose to
    do so as an exercise of discretion, we have no jurisdiction
    to review its decision. The government concedes that under
    United States v. Mummert, this matter should be remanded
    to afford the district court an opportunity to explain its
    refusal to grant Powell's pro se motion. In Mummert, as
    here, the defendant appealed the district court's failure to
    grant a requested downward departure following a guilty
    _________________________________________________________________
    3. In the alternative, Powell argues that he should be allowed to
    withdraw his guilty plea.
    4. Federal Rule of Criminal Procedure 11(h) provides:
    (h) Harmless Error. Any variance from the procedures required by
    this rule which does not effect substantial rights shall be
    disregarded.
    Fed. R. Crim. P. 11(h).
    7
    plea. The district court had not given any explanation for
    denying Mummert's request. We remanded stating:
    in cases such as this, where the record does not make
    clear whether the district court's denial of departure
    was based on legal or discretionary grounds, we believe
    that the appropriate course of action is to vacate the
    sentence and remand for the district court to clarify
    the basis for its 
    ruling. 34 F.3d at 205
    .
    Accordingly, we will remand so that the district court can
    clarify its rejection of Powell's motion for a downward
    departure.
    B. Powell's Sentence
    Powell's supervised release presents a more difficult
    question. Powell contends that he is entitled to specific
    performance of the plea agreement or, in the alternative,
    withdrawal of his guilty plea. As noted above, Powell's
    written plea agreement expressly stated that the court
    could not impose more than three years of supervised
    release. Similarly, the Assistant United States Attorney
    informed Powell that he was not exposed to more than
    three years of supervised release at the Rule 11 change of
    plea hearing, and that statement was never corrected by
    the court. However, Powell's sentence included a five year
    term of supervised release as allowed under 18 U.S.C.
    S 924. Powell therefore argues that he did not voluntarily
    and intelligently change his plea, and that the government
    breached its "promise" that he would not be exposed to
    more than three years of supervised release. We will
    address each argument in turn.5
    _________________________________________________________________
    5. Powell also argues that we should vacate his sentence based on our
    decision in United States v. Gilchrist, 
    130 F.2d 1141
    , 1133 (3d Cir.
    1997), where we vacated the defendant's sentence because the district
    court caused a breach of the defendant's guilty plea agreement. There,
    however, the parties entered into a guilty plea agreement pursuant to
    Rule 11(e)(1)(C), which is binding on the court once accepted. Because
    there is no indication in the record before us that the parties entered
    into the guilty plea agreement here pursuant to Rule 11(e)(1)(C), we find
    that this assertion is without merit, and need not be addressed.
    8
    1. Whether Powell Entered the Plea Voluntarily
    and Intelligently
    Fed. R. Crim. P. 11 was formulated to ensure that a
    defendant's guilty plea represents a voluntary and
    intelligent decision to waive fundamental protections. See
    North Carolina v. Alford, 
    400 U.S. 25
    , 30 (1970); McCarthy
    v. United States, 394 U.S.459, 465 (1969). Accordingly,
    under Fed. R. Crim.P. 11(c) "[b]efore accepting a plea of
    guilty . . . the court must address the defendant personally
    in open court and inform the defendant of, and determine
    that the defendant understands . . . the maximum possible
    penalty provided by law, including the effect of any. . .
    supervised release term." It is undisputed that Powell was
    misinformed about the length of supervised release that he
    could receive.
    Nevertheless, not all Rule 11 errors invalidate a guilty
    plea. Fed. R. Crim. P. 11(h), entitled "Harmless Error,"
    provides that "[a]ny variance from the procedures required
    by [Rule 11] which does not affect substantial rights shall
    be disregarded." Accordingly, we must determine if the
    misinformation here affected Powell's substantial rights.
    Every circuit court of appeals that has considered a case
    involving a defendant who is misinformed as to the
    maximum term of supervised release, but who receives a
    sentence with a combined term of imprisonment and
    supervised release that is less than the maximum possible
    penalty has concluded that the misinformation constituted
    harmless error. See United States v. Raineri, 
    42 F.3d 36
    (1st Cir. 1994); United States v. Andrades, 
    179 F.3d 131
    (2d Cir. 1999); United States v. Gracia, 
    983 F.2d 625
    (5th
    Cir. 1993); United States v. Fuentes-Mendoza, 
    56 F.3d 1113
    _________________________________________________________________
    Similarly, we need not address Powell's Apprendi claim. Powell's
    sentence was enhanced based upon prior convictions that he conceded
    in his plea agreement. Accordingly, Apprendi does not apply. See
    
    Apprendi, 120 S. Ct. at 2362-63
    ("other than the fact of a prior
    conviction,
    any fact that increases the penalty for a crime beyond the statutory
    maximum must be submitted to a jury and proved beyond a reasonable
    doubt.") (emphasis added).
    9
    (9th Cir. 1995); United States v. Barry, 
    895 F.2d 702
    (10th
    Cir. 1990).
    Perhaps because of this seemingly uniform approach, the
    government urges us to adopt a blanket rule that"a failure
    to explain a supervised release term at a Rule 11 hearing is
    harmless error if the term of incarceration imposed,
    combined with the term of supervised release imposed, is
    less than the maximum sentence [the defendant was aware
    of]." Government's br. at 15. However, we do not think that
    a blanket rule is appropriate.
    In United States v. Cleary, 
    46 F.3d 307
    , 311 (3d Cir.
    1995), we held that a habeas petitioner under 28 U.S.C.
    S 2255, must show prejudice to obtain collateral relief for a
    Rule 11 violation. There, the sentencing court failed to
    explain the "effects of special parole, including the
    consequences of a violation, and that special parole is
    different from and in addition to regular parole." 
    Id. at 310.
    We held: "[n]ot only must Cleary demonstrate an error of
    constitutional magnitude, but he also must show that he
    was prejudiced by that error, i.e., that he did not
    understand the consequences of his plea or that, if he had
    been properly advised about the effect of special parole, he
    would not have pled guilty." 
    Id. We found
    that the failure
    there "did not rise to that level." 
    Id. However, we
    have not previously addressed this precise
    question on direct appeal. The government rests its
    argument for a bright line rule in part upon United States
    v. Electrodyne Systems Corp., 
    147 F.3d 250
    (3d Cir. 1998).
    There, the district court erred in advising the defendant of
    the correct statutory fine for the offense charged in one of
    the counts to which the defendant pled guilty. 
    Id. at 252.
    The court did, however, correctly advise the defendant of
    the maximum fine that could be imposed on the remaining
    count. The total fine that the court ultimately imposed was
    less than the stated total maximum on both counts. On
    direct appeal, we held that the court's error as to the
    amount of the fine on one count was harmless. We
    concluded that, "when all is said and done, the immutable
    fact is . . . Defendant was fined . . . an amount below the
    exposure about which it was informed." 
    Id. at 253.
    10
    Nevertheless, though the analysis in Electrodyne is
    certainly relevant to our inquiry here, the case is
    distinguishable from the instant case because the
    defendant there was misinformed about a fine. Supervised
    release "is a deprivation of some portion of one's liberty
    imposed as a punitive measure for a bad act." United States
    v. Dozier, 
    119 F.3d 239
    , 242 (3d Cir. 1997)."A defendant
    on supervised release is subject to various terms and
    conditions which restrict his freedom and which make him
    vulnerable to further punishment should he violate them.
    Such subsequent punishment may again include more
    imprisonment and more supervised release." 
    Id. We cannot
    assume that misinformation about a possible deprivation of
    liberty is equivalent to misinformation about a monetary
    penalty.
    The government also relies on our decision in United
    States v. Mustafa, 
    238 F.3d 485
    (3d Cir. 2001), where we
    also addressed errors in a Rule 11 colloquy in the context
    of a direct appeal. One of the arguments that we rejected in
    Mustafa is relevant to the government's position here.
    Mustafa argued that the sentencing court erred in not
    inquiring into promises that had been made in relation to
    the change of plea. After reviewing the record we concluded
    that "the only reasonable conclusion that this record
    supports is that Mustafa had been advised of counsel's best
    estimate of what the court would actually impose, and
    Mustafa was interpreting counsel's estimate as a`promise'
    as to the sentence he was going to receive." 
    Id. at 491-92.
    We noted:
    Mustafa said absolutely nothing after his attorney
    informed the court of guidelines discussions, and he
    never said anything to suggest that his affirmative
    response about other promises was anything more
    than a reference to `assurances' he had received from
    his attorney as to what sentence would most likely be
    imposed.
    Mustafa was told that the total maximum sentence was
    830 years of imprisonment. The sentence of
    imprisonment he received, though substantial (135
    months), was far less than the maximum that he was
    aware of. Moreover, any alleged misrepresentations
    11
    that Mustafa's former counsel may have made
    regarding sentencing calculations were dispelled when
    Mustafa was informed in open court that there were no
    guarantees as to sentence, and that the court could
    sentence him to the maximum. Thus, we conclude that
    Mustafa's answering `yes' to the court's inquiry about
    promises is not grounds to invalidate his plea.
    
    Id. Immediately thereafter,
    we stated the following in a
    footnote:
    We recognize that the maximum sentence authorized
    by law is often so extraordinarily long that few
    defendants other than `career criminals' plead guilty
    with the expectation that the maximum sentence
    applies to them. However, all that the law requires is
    that the defendant be informed of his/her exposure in
    pleading guilty. The law does not require that a
    defendant be given a reasonably accurate `best guess'
    as to what his/her actual sentence will be; nor could it,
    given the vagaries and variables of each defendant's
    circumstances and offending behavior. See United
    States v. Cleary, 
    46 F.3d 307
    , 311 (3rd Cir. 1995).
    
    Id. n.5.6 The
    government now argues that Mustafa creates a
    blanket rule that Rule 11 error is harmless so long as the
    defendant is not sentenced to a term longer than the
    maximum he or she is advised of. Put another way, the
    government is arguing that any such discrepancy could not
    have affected Powell's decision to plead guilty because the
    sentence imposed was within the range of possibilities a
    defendant accepts when deciding whether to plead guilty.
    We disagree. Such a bright line rule obfuscates its own
    underlying rational, and Mustafa is not to the contrary.
    _________________________________________________________________
    6. Mustafa also argued that the district court committed reversible error
    in not informing him that restitution could be ordered as part of the
    sentence in violation of Rule 11(c)(1). We noted that the government had
    advised Mustafa "that he faced a fine of several million dollars but was
    actually ordered to pay far less than that amount in restitution." 
    Id. at 490
    (emphasis in original). While recognizing that restitution is not the
    same as a fine, we relied on Electrodyne and found the distinction
    irrelevant in context of that specific Rule 11 error. 
    Id. at 490
    .
    12
    Mustafa is distinguishable from the case at bar because
    here the government affirmatively misled Powell during the
    plea colloquy and in the guilty plea agreement as to the
    maximum supervised term he could receive. In contrast,
    Mustafa involved the defendant interpreting his own
    counsel's best estimate as a "promise" as to the sentence he
    would receive. We acknowledged that few defendants
    actually expect that they will receive the statutory
    maximum they have been informed of,7 but explained that
    the law does not require that the defendant be given an
    accurate guess of what his or her ultimate sentence will be.
    Common sense suggests that a defendant's realistic
    expectation of the sentence he or she will receive will often
    include considerations of applicable ranges under the
    Sentencing Guidelines. However, the colloquy under Rule
    11 occurs when a defendant first enters a guilty plea. This,
    in turn, will almost always occur before the sentencing
    court has an opportunity to review a Presentence Report.
    Accordingly, the court will not be in a position to know
    what the realistic sentencing range will be when the court
    explains the maximum range of sentences to the defendant
    at the Rule 11 hearing.
    While the Sentencing Guidelines certainly are a
    relevant consideration for defendants entering a plea of
    guilty, the district court at the time of the plea
    allocution frequently has too little information available
    to provide defendant with an accurate sentencing
    range. For example, probation department officials
    often have not scored or researched defendant's
    criminal history, and the court is unaware of upward
    or downward departure motions that the government
    or defense counsel may pursue. Both of these factors
    have significant impacts on Sentencing Guideline
    calculations.
    _________________________________________________________________
    7. Several other circuit courts of appeals have also observed that a
    defendant might reasonably expect that he or she will not be sentenced
    to the statutory maximum. See United States v. 
    Raineri, 42 F.3d at 42
    ;
    United States v. 
    Andrades, 169 F.3d at 134
    ; United States v. Whyte, 
    3 F.3d 129
    , 130 (5th Cir. 1993).
    13
    
    Andrades, 169 F.3d at 134
    .
    The court in Andrades, cited United States v. Raineri, in
    declaring: "we decline to adopt an inflexible rule" for
    resolving issues under Rule 11(h) 
    Id. As we
    discuss below,
    Raineri provides for an individualized and flexible inquiry
    into determinations of harmless error under Rule 11(h).
    Nevertheless, despite its pronouncement that it was
    "declin[ing] to adopt an inflexible rule," the court in
    Andrades established what appears to be the kind of bright
    line inflexible rule urged upon us here. The court stated:
    We now join with those circuit courts of appeals
    holding that the error is harmless where the district
    court misinforms a defendant of the applicable
    supervised release term and the total sentence of
    imprisonment and supervised release actually imposed
    is less than that described during the plea 
    allocution. 169 F.3d at 134
    .
    We believe the court in Andrades was correct in stating
    its intent to reject a bright line rule based upon the
    reasoning in United States v. Raineri. First of all, we note
    that the Supreme Court has cautioned against taking
    errors committed during guilty plea proceedings lightly. See
    McCarthy v. United States, 
    394 U.S. 459
    (1969). A bright
    line rule, while easy to apply, minimizes the importance of
    the inquiry that must be undertaken when examining an
    individual decision to waive fundamental constitutional
    guarantees as is the case when a defendant enters a guilty
    plea. Accordingly, "[a]s the Advisory Notes to the 1983
    amendment to Rule 11 (adding subsection 11(h)) indicate,
    `it is still true, as the Supreme Court pointed out in
    McCarthy, that thoughtful and careful compliance with Rule
    11 best serves the fair and efficient administration of
    criminal justice. . . .' " United States v. Barry, 
    895 F.2d 702
    ,
    705 (10th Cir. 1990). We believe the government's position
    here moves us away from thoughtful and careful
    compliance with Rule 11 and towards mechanical inquiries
    into violations of the Rule.
    Moreover, the difficulty in establishing a bright line rule
    is evidenced by the varying approaches that courts of
    appeals have taken in attempting to define harmless error
    14
    under Rule 11.8 The practical difficulty of such an approach
    is exemplified in the thoughtful analysis of the Court of
    Appeals for the First Circuit in Raineri. There, the court
    provides the following hypothetical:
    imagine a defendant who is wrongly told at the Rule 11
    hearing that the maximum penalty for his crime is five
    years when in fact the maximum penalty is 15 years.
    The defendant might fairly expect, given his own past
    history and limited role in the offense, that the
    maximum sentence (whatever it might be) would not be
    likely to be imposed. If he then pled guilty and
    thereafter received a five-year sentence, he might
    reasonably think that the misinformation had
    prejudiced him in a rather concrete 
    way. 42 F.3d at 41
    (1st Cir. 1994) (citing United States v. Whyte,
    
    3 F.3d 129
    , 130 (5th Cir. 1993)).9 The defendant in this
    _________________________________________________________________
    8. See, e.g., United States v. Johnson, 
    1 F.3d 296
    , 302 (5th Cir. 1993)
    (en
    banc) (focusing on "whether the defendant's knowledge and
    comprehension of the full and correct information would have been likely
    to affect his willingness to plead guilty"); United States v. Goins, 
    51 F.3d 400
    , 402 (4th Cir. 1995) (same); United States v. 
    Raineri, supra
    ,
    (ascertaining whether the Rule 11 error led the defendant to reasonably
    expect a lesser sentence than he actually received); United States v.
    
    Andrades, supra
    , (refusing to adopt a rigid rule; United States v.
    Fuentes-
    Mendoza, 
    56 F.3d 1113
    , (9th Cir. 1995) (stating generally that error was
    harmless where the maximum term of restricted liberty that the
    defendant faced was less than the sentence he or she was informed of);
    United States v. 
    Barry, supra
    , (determining whether the Rule 11 error
    had a "significant influence" on the defendant's decision to plead
    guilty);
    United States v. Syal, 
    963 F.2d 900
    , 906 (6th Cir. 1992) (stating that
    "[s]ubstantial rights may not be affected when a defendant is informed of
    the maximum penalty and that penalty markedly exceeds the penalty the
    defendant received, including the period of supervised release and any
    additional incarceration time that might result from violation of [the]
    supervised release condition").
    9. The error in United States v. Whyte, was far more egregious than the
    error here. There, the defendant's written plea agreement informed him
    he "was subject to a minimum term of five years, and a maximum term
    of twenty years imprisonment, a minimum term of four years supervised
    release, and a fine of up to $2,000,000." 
    Whyte, 3 F.3d at 129
    . The
    district court confirmed those ranges during the Rule 11 colloquy.
    15
    example might well be able to convince a reviewing court
    that the misinformation severely hampered his ability to
    tender an intelligent and knowing guilty plea because he
    was precluded from assessing the risks and benefits of
    pleading guilty. In the words of the Court of Appeals for the
    Fifth Circuit, the defendant's knowledge of the correct
    information "would have been likely to affect his willingness
    to plead guilty." 
    Johnson, 1 F.3d at 302
    .
    The court in Raineri, therefore appropriately focused
    upon whether "the misinformation . . . at the Rule 11
    hearing lead [the defendant] to expect a lesser penalty than
    he actually received." 
    Id. at 42.
    In doing so, the court
    rejected the position of those courts that have concluded
    that "a defendant should not be heard to complain if he
    ultimately gets the benefit of the lesser sentence that was
    inaccurately described . . . [when he pled guilty]" so long as
    the sentence is less than the sentence indicated by the
    judge. 
    Id. at 42
    (citing cases).10
    Although the inquiry into what the defendant might fairly
    expect can sometimes be answered by focusing upon the
    defendant's awareness of his or her maximum exposure,
    the example in Raineri demonstrates that such an approach
    _________________________________________________________________
    However, "[i]n truth, Whyte was subject to a mandatory minimum term
    of ten years, not five, a possible maximum term of life, not twenty years,
    a supervised release term of five years, not four, and a fine of
    $4,000,000, not $2,00,000." 
    Id., at 130.
    Nevertheless, the district court
    subsequently held that its failure to inform Whyte of the correct
    exposure was harmless error. The court of appeals reversed.
    10. We recognize that some of the language of the opinion in Raineri, like
    the language in Andrades, suggests that the court is applying a bright
    line rule. For example, the court states: "[c]ourts have commonly held
    that such errors are harmless when the defendant receives a combined
    sentence of imprisonment and supervised release that is less than the
    maximum term of imprisonment earlier described. The same rule is
    followed where the defendant is required to pay restitution in an amount
    less than the potential fine of which he is 
    warned." 42 F.3d at 42
    .
    However, we do not interpret the court as adopting such a rule --
    especially in view of the persuasive and helpful hypothetical we have
    quoted above. Rather, we believe the court was simply noting that a
    bright line rule has been used to resolve issues arising under Rule 11.
    16
    will not always resolve the analysis in a manner consistent
    with the gravity of the court's inquiry or the fundamental
    rights that are involved. We must not forget that the proper
    inquiry here is the validity of the defendant's waiver of
    constitutional guarantees.
    This is a subjective, highly individualized test. We must
    focus on the defendant's ability to tender a knowing and
    intelligent waiver of constitutional rights given the
    misinformation he or she received. 
    Johnson, supra
    . For
    example, in United States v. Goins, 
    51 F.3d 400
    (4th Cir.
    1995), the trial court's failure to properly inform a
    defendant about a mandatory sentence was ruled not to be
    harmless under Rule 11(h). In reviewing the error, the court
    of appeals focused upon "whether the defendant's
    knowledge and comprehension of the full and correct
    information would have been likely to affect his willingness
    to plead guilty." 
    Id. at 402
    (citing United States v. 
    Johnson, 1 F.3d at 302
    .)11
    We conclude that an error will be regarded as harmless
    under Rule 11(h) only if the government can establish that
    the error is unlikely to have affected a defendant's
    willingness to waive his or her rights and enter a plea of
    guilty. See United States v. Reynoso, 
    254 F.3d 467
    , 475 (3d
    Cir. 2001) (distinguishing the burden of proof under
    harmless error review from the burden of proof under plain
    error review).
    In conducting that inquiry we must obviously consider
    the nature of the error, and determine if, given the entire
    record (including the defendant's individualized
    circumstances, criminal record, role in the offense, and
    concession for pleading guilty), it affirmatively appears
    unlikely that the error materially hampered his or her
    _________________________________________________________________
    11. In making this determination, the court alluded to three factors: 1)
    "what the defendant actually knows when he pleads guilty on the basis
    of an affirmative indication in the record;" 2) the additional information
    the defendant would have been advised of in compliance with Rule 11;
    and 3) "how the additional or corrected information would have likely
    affected the defendant's decision." 
    Id. (citing United
    States v. Padilla,
    
    23 F.3d 1220
    , 1222 (7th Cir. 1994) and United States v. Johnson, 
    1 F.3d 296
    , 302 (5th Cir. 1993)).
    17
    ability to assess the risks and benefits of pleading guilty. At
    first blush, it may appear that such an inquiry is very
    straightforward whenever, as here, a defendant is
    misinformed about the amount of supervised release he or
    she is exposed to, but is correctly informed that the
    maximum incarceration is life imprisonment, and the
    ultimate sentence (including supervised release) is
    substantially less than life. However, focusing only upon
    the severity of the maximum sentence will sometimes
    oversimplify the inquiry. See 
    Raineri, supra
    .
    A defendant with a history of addiction may plead guilty
    in return for a sentence that lengthens imprisonment while
    reducing supervised release, and not plead guilty to a
    sentence with a longer "tail" of supervised release and a
    somewhat shorter period of incarceration. Such a defendant
    may feel that his or her addiction will so impact the
    potential for successful special parole that extended
    incarceration provides a better chance of rehabilitation
    and/or less confinement in the "long run." If such a
    defendant is misinformed about the amount of supervised
    release that can be imposed he or she may not be able to
    accurately gauge the risks of pleading guilty. The resulting
    error may not be harmless therefore, even if the sentence
    that is ultimately imposed is less than the maximum
    imprisonment authorized by law and explained to
    defendant.
    Here, Powell was on probation at the time of the instant
    offense. As discussed above, he may have concluded,
    despite his horrendous prior record, that he would not
    receive the maximum sentence. However, given his criminal
    history, a statutory maximum of life imprisonment, and
    Powell's knowledge that the court had to impose at least the
    15 year mandatory minimum, we can not agree that the
    error in informing him of supervised release hampered his
    ability to gauge the risks and benefits of pleading guilty.
    Nothing on this record supports that claim. We recognize
    that Powell expected that he would not receive more than
    three years of supervised release. The supervised release
    term, however, is only one of the many factors that Powell
    had to weigh when deciding whether or not to plead guilty.
    18
    Before pleading guilty Powell understood that the
    government would make whatever sentencing
    recommendation it deemed appropriate. Powell agreed that
    the court could impose a sentence of life imprisonment, and
    that the court had to impose at least the 15-year
    mandatory minimum term of imprisonment and a three
    year term of supervised release. Powell was aware that the
    court was not bound by any of the terms of the plea
    agreement, and that he could not withdraw his plea if the
    court declined to follow any recommendation, motion or
    stipulation contained in the agreement. Powell and the
    government also stipulated that Powell's offense level was a
    33 and that he was eligible for a three-level downward
    departure for acceptance of responsibility. The sentence
    reduction triggered by that departure would have been lost
    if Powell had chosen to go to trial.
    Despite Powell's current focus on the extra two years of
    supervised release that he was not expecting, we are
    satisfied that he would not have done anything differently
    had he known that he was exposing himself to five years of
    supervised release as opposed to three years at the
    conclusion of his prison sentence. Accordingly, we hold that
    the error here was harmless under Rule 11(h). That does
    not, however, mean that Powell is entitled to no relief.
    2. Whether the Government Breached the
    Guilty Plea Agreement
    Powell contends that he is entitled to specific
    performance because the government breached the guilty
    plea agreement that told him that he was only exposed to
    a maximum term of three years of supervised release. As
    noted above, it is undisputed that the government did
    inform him that the plea would only expose him to three
    years supervised release, and the court confirmed that at
    the change of plea hearing.
    However, to the government's credit, following oral
    argument, the United States Attorney's Office sent a letter
    stating that it would recommend a three-year term of
    supervised release on remand if the district court asks for
    a recommendation from the government. The government
    explained:
    19
    The reason is that . . . if the defendant is given the
    benefit of the doubt the plea agreement may
    conceivably be read as a promise by the government to
    recommend a term of supervised release of no more
    than three years. If that is accurate, and in order to be
    conservative, we assume it is, that means the
    government is bound by its agreement not to make any
    representation to the district court inconsistent with
    the plea agreement. See, e.g., United States v. Nolan-
    Cooper, 
    155 F.3d 221
    , 236 (3d Cir. 1998). While the
    district court has authority under the plea agreement
    to enter any legal sentence, the government may not
    contradict any promise it made regarding the position
    the government will take.
    Letter dated March 9, 2001 from Asst. U.S. Atty. Robert A.
    Zauzmer, Esq. and Asst. U.S. Atty. Kathleen Rice, counsel
    for the government. We commend AUSAs Zauzmer and Rice
    for their candor and the fairness of the position they have
    taken here. Inasmuch as we must remand this matter
    under United States v. Mummert in any event to resolve the
    motion for a downward departure, and inasmuch as the
    government is willing to make this recommendation upon
    remand, we conclude that the issue of Powell's supervised
    release is best resolved by affording the government an
    opportunity to allow the district court to request a
    recommendation, and then sentence in the manner the
    court deems most appropriate under these circumstances.
    IV. Conclusion
    For the foregoing reasons, we will vacate the sentence
    and remand to the district court for clarification of its
    reasons for denying Powell's pro se motion for downward
    departure. The district court will then have an opportunity
    to elicit the government's position regarding resentencing in
    view of Powell's claim for specific performance.
    A True Copy:
    Teste:
    Clerk of the United States Court of Appeals
    for the Third Circuit
    20