Second Circuit Rejects Sentence Based on Government’s Dramatic Shift From its Pre-Plea Pimentel Estimate
In United States v. Walker, 17-1896-cr (Jacobs, Calabresi, and Rakoff, by designation) (April 4, 2019), the Second Circuit held that the Government breached its plea agreement with the defendant by advocating for a term of imprisonment that was substantially higher than the Government’s initial sentencing estimate in the plea agreement. In support of the increased sentence, the Government pointed only to information known to the Government at the time of the plea. The decision addresses so-called “Pimentel estimates” used in the Eastern District of New York, in which the Government provides the defendant with pre-sentencing notice of its calculation of the applicable Sentencing Guidelines range in a plea agreement, while cautioning that this estimate may change in the future. The panel held that, at least on these facts, the defendant was entitled to rely on the Government’s Pimentel estimate despite the cautionary language and, accordingly, the Government unlawfully changed its position based on information known from the outset. As a result, the case will be remanded for resentencing to a new district judge.
In late 2010, Defendant Shondell Walker and eleven others were arrested and charged with running a drug conspiracy in the Gowanus Houses, a public housing development in Brooklyn. The criminal complaint alleged that the defendants “regularly sold crack cocaine from residences and public spaces” and were “involved in various acts of violence . . . , including multiple shootings and at least three murders.” The complaint further alleged that Walker was the primary security guard and enforcer for Ronald Herron, the organization’s leader. Walker allegedly carried firearms to drug transactions, robbed and/or attacked rival drug traffickers, and participated in a shooting against a rival drug trafficker.
In October 2011, Walker entered into an agreement with the Government to plead guilty to one count of conspiracy to distribute at least 200 grams of cocaine in violation of 21 U.S.C. § 846. In the plea agreement, the Government provided its “estimate” that Walker’s adjusted offense level under the Sentencing Guidelines was 29, resulting in a Guidelines range of 108 to 135 months’ imprisonment. The Government further agreed that, “based upon information now known to the [Government],” it would “take no position concerning where within the Guidelines range determined by the Court the sentence should fall,” and would “make no motion for an upward departure under the Sentencing Guidelines.” However, the plea agreement stated that the Government’s Guidelines estimate was “not binding on the [Government], the Probation Department or the Court.” It further cautioned that “[i]f the Guidelines offense level advocated by the [Government], or determined by the Probation Department or the Court, is, for any reason, including an error in the estimate, different from the estimate, the defendant will not be entitled to withdraw the plea and the government will not be deemed to have breached this agreement.”
In January 2012, the Probation Department prepared a Pre-Sentence Report in anticipation of sentencing. According to the Report, Walker acted as an “enforcer” for the drug organization and “carried a firearm as part of his role in the organization.” The Report further indicated that the Government “conservatively estimates that Herron’s organization distributed in excess of 1 kilogram of crack cocaine,” all of which could be attributed to Walker based on his role in the conspiracy.
Walker’s sentencing was initially scheduled for September 2013. But the district court postponed sentencing at the Government’s request—and over Walker’s objection—until after Herron’s trial. At Herron’s 2014 trial, several witnesses testified that Walker was an enforcer in the organization, carried a gun, and threatened people to protect Herron’s territory. Walker himself testified for Herron, claiming that Herron had no role in the conspiracy and he sold drugs only to support himself. Herron was convicted and ultimately sentenced to twelve life sentences.
In October 2016, five years after Walker’s guilty plea, the Government submitted a second sentencing memorandum with a “revised” Guideline recommendation. The Government now stated that Walker’s adjusted offense level under the Sentencing Guidelines was 34, based on trial testimony attributing at least one kilogram of crack cocaine to Walker, his use of a dangerous weapon, and his perjurious testimony. The corresponding Guidelines range was 360 months to life. Walker was finally sentenced in May 2017 and the district court adopted the Government’s revised Guidelines calculation. The court sentenced Walker to 360 months’ imprisonment and five years of supervised release. This sentence was more than three times as long as the low end of the stipulated Guidelines range set forth in Walker’s plea agreement.
The Court’s Decision
On appeal, Walker argued principally that the Government breached the plea agreement by advocating for a higher Guidelines range and a higher sentence than it had agreed to in the plea agreement. As a threshold matter, the Court determined that Walker had adequately preserved this argument and so conducted a harmless error review. This determination was critical because the Second Circuit has previously held that given the legal uncertainty in this area (described below), the Government’s abandonment of a Guidelines range in a plea agreement cannot constitute plain error. United States v. MacPherson, 590 F.3d 215, 219 (2d Cir. 2009).
The Court began its analysis by observing that plea agreements are interpreted according to typical contract law principles. The reviewing court holds the Government to “meticulous standards of performance” because such agreements require defendants to waive fundamental constitutional rights, such as the presumption of innocence and right to a trial by jury.
The Government’s practice of including estimated Guidelines ranges in plea agreements dates back at least to the Second Circuit’s decision in United States v. Pimentel, 932 F.2d 1029 (2d Cir. 1991). In Pimentel, the defendant argued that after entering into a guilty plea he was unfairly surprised by the calculation of the applicable Guidelines range and resulting severity of the sentence imposed. The Court rejected that claim, but wrote that it would be good practice for the Government to provide pleading defendants with “the likely range of sentences that their pleas will authorize under the Guidelines,” while recognizing that “the Government is under no legal obligation to provide this information.” Id. at 1034.
It is now routine practice for the Government to provide a “Pimentel estimate” prior to a plea or sentencing, while also cautioning that the estimate is not binding on the Government or the Court. As the panel explained, the Second Circuit has not been entirely consistent in holding the Government to its estimated Guidelines range. In United States v. Palladino, for example, the Government provided a Pimentel estimate in a plea agreement that excluded a sentencing enhancement for intent to carry out a threat, but then advocated for that enhancement at sentencing. 347 F.3d 29, 31-32 (2d Cir. 2003). The Circuit held that since the plea agreement specified that the estimated Guidelines range was “based on information known to the [Government] at this time,” the defendant “had a reasonable expectation that the Government would not press the Court for an enhanced offense level in the absence of new information.” Id. at 31, 34. Accordingly, the court vacated the judgment and remanded to allow the defendant to withdraw his guilty plea. Id. at 35.
The Second Circuit interpreted a plea agreement with a Pimentel estimate differently in United States v. Habbas, 527 F.3d 266 (2d Cir. 2008). There, like in Palladino, the Government failed to include a particular sentencing enhancement in its Pimentel estimate, but then sought application of the enhancement at sentencing. Id. at 270. The court nonetheless held that the plea agreement was enforceable and the defendant could not withdraw his plea despite the Government’s change in position. The court reasoned that the Government’s failure to include the enhancement in its Pimentel estimate was a “mistake” and “there is no suggestion that the government acted in bad faith.” Id. at 271. The court distinguished Palladino on two grounds. First, unlike in Palladino, Habbas’ plea agreement did not include language stating that the Government’s Pimentel estimate was “based on information known to the government” at that time. Second, the Abbas panel distinguished Palladino’s unique concern that the Government had revised its sentencing estimate only because the case had been assigned to a different Assistant United States Attorney with a different view of the appropriate sentence. Id. at 272.
The Court here held that the present facts were more analogous to Palladino than Abbas. Like in Palladino, Walker’s plea agreement specified that the Pimentel estimate was “based upon information now known to the [Government],” and the Government agreed it would only change its position if new information became known after the plea. The Court then detailed at length that the Government’s proffered bases for seeking a higher sentencing range—Walker was reasonably connected to the distribution of at least a kilogram of crack cocaine, he carried a gun and threated people, and he acted as an enforcer—were all known to the Government at the time of the plea. Further, the case presented somewhat unusual and extreme circumstances: the Government had successfully delayed Walker’s sentencing for four years while it tried his co-defendant, and then sought a dramatic upward enhancement of the applicable sentencing range—from 108 to 135 months in the plea agreement to 360 months to life at sentencing. Taken together, the Court concluded that the Government had violated Walker’s “reasonable expectations,” and the cautionary language in the plea agreement had not put Walker “on notice about this particular degree and kind of change.”
The Court rejected the Government’s argument that the information it relied on was “new” because it only became actionable when developed during Herron’s trial. It was sufficient that, at the time of the plea, “the Government knew about Walker’s activities and, based on that, made the conscious choice to exclude certain enhancements from Walker’s plea agreement.” And the Court held that the Government’s conduct produced “serious unfairness” regardless of whether it had acted in bad faith—reasoning that is in some tension with Abbas’ heavy reliance on the absence of bad faith. The Court concluded that the proper remedy was specific performance of the plea agreement (i.e. resentencing with a Pimentel estimate of 108 to 135 months) with a different district judge (as was done in prior plea-agreement-violation cases and not owing to any perceived unfairness on the part of the district judge).
This case represents another chapter in the Second Circuit’s efforts to interpret and apply Pimentel estimates included in plea agreements. In our view, the Court rightly recognizes that it is unjust for the Government to surprise a criminal defendant who has entered into a plea agreement with a significantly higher Guidelines range at sentencing, based on no new information, and then bar the defendant from withdrawing his plea. The boilerplate cautionary language in the plea agreement does little to ameliorate this concern, particular where, as here, the Government’s interpretation of that language would effectively render its Pimentel estimate illusory.
On the other hand, the Second Circuit has been correct in observing that as long as the Government is not required to provide a defendant with pre-sentencing notice of the applicable Guidelines Range, holding the Government too stringently to its Pimentel estimate may have the unintended effect of pushing the government to propose higher Pimentel estimates and then sometimes to seek those higher sentences. Or it may lead the government to propose higher Pimentel estimates regardless of whether it ultimately will seek those sentences, thereby depriving the ordinary defendant of the benefit that comes from receiving a useful Pimentel estimate prior to a guilty plea. Neither of these outcomes would aid defendants in deciding whether to plead guilty based on an assessment of the likely Guidelines range.
In weighing these competing concerns, we think the Court here strikes the right balance. It is good practice for the Government to provide defendants with pre-plea Guidelines estimates, as proposed by the Circuit in Pimentel, and it is reasonable for the defendant to assume that the estimate is based on all information known to the Government at the time of the plea—regardless of the precise cautionary language (or lack thereof) in the plea agreement. As such, the defendant should either be permitted to withdraw from his plea if the Government seeks to modify its proffered Guidelines range based on information it knew prior to the plea, or the Government should be held to the stipulated range. To be sure, it can be reasonable for the Government to seek additional upward enhancements in calculating the Guidelines range if it truly learns additional information post-plea. And no agreement can prohibit the government or the defense from providing truthful information to the Court or to the Probation Department in connection with sentencing. Such information should be considered by the sentencing court in calculating the correct Guidelines range and fashioning a just and proper sentence, regardless of the terms of the plea agreement.
 Walker also argued that the lengthy postponement between plea and sentencing violated his Fifth Amendment right to a speedy sentencing. The Court did not reach this issue.
 This appeal arises out of the Eastern District, where the Government typically includes an estimated Guidelines range in its plea agreement that is not meant to be binding on the parties. In contrast, in the Southern District of New York, the Government provides Pimentel estimates to defendants who plead guilty without a plea agreement. Such estimates are not signed by the defendant, do not waive the defendant’s rights to make arguments at sentencing or appeal the sentence, and do not bind either party, with the Government making an express reservation of rights. Plea agreements in the Southern District (other than for cooperating witnesses) ordinarily include a stipulated Guidelines range and foreclose either party from seeking a different Guidelines calculation at sentencing. Since this appeal and the Palladino and Habbas appeals discussed below all arise out of the Eastern District, one wonders if the Eastern District might consider revising its practices in this area.
 When Habbas was decided, one commentator observed that it was a “confusing” and “bizarre” opinion because “it turns on a close reading of the plea agreement, without reproducing the language of the agreement itself.”
 The Court reserved for the district court to determine on remand whether a sentencing reduction for acceptance of responsibility should be removed in light of Walker’s perjurious testimony at Herron’s trial.