Pre-Plea Estimates of Jail Time

In 1991, the Second Circuit discussed the then-emerging problem of criminal defendants being given prison sentences significantly higher than the defendants expected because of the new (and then mandatory) federal Sentencing Guidelines. United States v. Pimentel, 932 F.2d 1029 (2d Cir. 1991). One of the defendants had pled guilty to a drug offense but challenged his sentence because the district court sentenced him based on aggravating evidence adduced at the trial of his co-defendants. The Second Circuit upheld the district court's sentence, but said that it was “quite troubled by the escalating number of appeals” by defendants who pled guilty to crimes but then were surprised by the severity of the sentences imposed on them. The Second Circuit noted that, given its own struggles to date in interpreting the Sentencing Guidelines, it was “not unsympathetic” to claims by defendants who did not fully appreciate the consequences of their pleas. Indeed, the Second Circuit intimated that some variances between the sentence reasonably expected by a defendant and the sentence actually imposed might be so unfair as to raise questions about the validity of the plea itself.

To deal with these concerns, the Second Circuit made a simple suggestion: Before entering into plea agreements, the government, with its “unique expertise in muddling through the complexities of the Guidelines,” could inform defendants of the likely sentencing range following a guilty plea. While the court made clear that the government was not legally obligated to provide such estimates, it nevertheless invited government attorneys to play a role in “helping to ensure that guilty pleas indeed represent intelligent choices by defendants.”

After Pimentel, U.S. Attorneys' Offices within the Second Circuit began providing defendants with so-called “Pimentel letters” as part of the plea process. Although the particular form and content of Pimentel letters has evolved over time, they generally: 1) set forth the government's position regarding the application of the (now advisory) federal sentencing guidelines to the defendant, including an estimate of the applicable guideline range; and 2) reserve the government's right to change its position regarding how the defendant should be sentenced after the plea.

Second Circuit Case Law After Pimentel

Following the Pimentel decision, a body of case law has developed in situations where the government ultimately seeks and obtains a sentence in excess of its Pimentel estimate.

For example, in United States v. Palladino, 347 F.3d 29 (2d Cir. 2003), the Second Circuit held that the government breached a plea agreement when it deviated from its Pimentel estimate. The defendant pled guilty to one count of transmitting a threat in interstate commerce. The plea agreement included a sentencing estimate
“[b]ased on information known to [the government] at this time.” After the plea was entered, but before the defendant was sentenced, the case was reassigned to a different prosecutor, who sought a tougher sentence based on an audio recording of the defendant that had been in the government's possession prior to the plea. The sentencing judge imposed the tougher sentence sought by the government, and the defendant appealed on grounds that the government breached his plea agreement.

The Second Circuit vacated the defendant's plea, holding that because the plea agreement contained a Pimentel estimate explicitly based on information then known to the government, it was “logical for the defendant to believe that the estimate, and the Government's stance at the sentencing hearing, would not be altered in the absence of new information or ' simply because a new Assistant United States Attorney had taken over the case and adopted a different view of the matter.”

In contrast, in United States v. Habbas, 527 F.3d 266 (2d Cir. 2008), the Second Circuit upheld a defendant's sentence even though the government sought a term of imprisonment in excess of its Pimentel estimate based on information known to it at the time of the plea. One of the defendants in Habbas pled guilty to obstructing a federal grand jury investigation. The government provided the defendant with a Pimentel calculation, but the Pre-Sentence Report prepared by the U.S. Probation Office included a recommendation for a longer prison sentence based on a factor that the government knew about, but had simply overlooked, at the time of the plea. At sentencing, the government acknowledged that its failure to account for the additional factor in its Pimentel estimate had been a “mistake” and asked for the longer sentence recommended by the Probation Office. The district court imposed the greater sentence sought by the government.

On appeal, the defendant, relying on Palladino, argued that the longer prison term violated his plea agreement because it was based on information known to the government at the time of his plea agreement. Notwithstanding Palladino, the Second Circuit upheld the defendant's sentence, largely on grounds that there was no evidence that the government had acted “abusively” or in bad faith when it provided its Pimentel guidance. The court explained that, in preparing the Pimentel calculation, the government “simply failed to notice the applicability” of the factor justifying an increased sentence. While recognizing that, “in certain circumstances government deviation from its prior estimate could conceivably produce serious unfairness,” the court nevertheless found that the government's mere failure to “notice the possibility” of a basis for seeking more prison time was not such a circumstance.

Thus, Habbas rejected both a broad reading of Palladino and a categorical rule that the government may deviate from a Pimentel estimate only where newly discovered facts justify the departure. “We think it would be foolhardy to attempt to set a broad rule, beyond noting the obvious importance of good faith on the government's part,” the court explained.

United States v. MacPherson

A recent Second Circuit opinion highlights that court's reluctance to find that a deviation from a Pimentel estimate constitutes a violation of a defendant's plea agreement. United States v. MacPherson, 590 F.3d 215 (2d Cir. 2009). MacPherson pled guilty to one count of conspiring to import narcotics. The Probation Office's Pre-Sentence Report recommended additional prison time based on considerations that were not included in the government's Pimentel calculation. The court imposed a sentence greater than that contemplated in the plea agreement.

While MacPhearson objected to his sentence in the district court, he did not specifically object on grounds that the sentence was inconsistent with the government's Pimentel submission. Thus, on appeal, the Second Circuit reviewed his sentence only for plain error and concluded that the district court's judgment should be upheld. The court noted that in light of the “conflicting outcomes” in Palladino and Habbas, and the fact that the defendant was put on notice in his plea agreement that the Pimentel estimate was non-binding, it was not “plain error” for the district court to impose the higher sentence sought by the government.

In a lengthy concurring opinion, Judge Jon Newman noted that “Palladino and Habbas are problematic, not only for their inconsistency but also for the uncertainty they risk for the use of Pimentel estimates.” Judge Newman would have resolved the “tension” between the two decisions by upholding “all plea agreements with Pimentel estimates, regardless whether the Government at sentencing advocates a higher Guideline range ' as long as the agreement makes clear that the Government is not bound by the estimate” and as long as the district court makes that fact clear during the plea allocution, along with the fact that the defendant will not be able to withdraw his plea if the actual sentence exceeds the Pimentel estimate.

Conclusion

Cases such as Habbas and MacPherson make clear the risk of relying on a Pimentel estimate in assessing the consequences of a guilty plea. A criminal defendant is well advised to take such estimates for what they are ' one piece of information in the sentencing process but not one that can be relied on.

Steven F. Reich ([email protected]), a member of this newsletter's Board of Editors, is co-chair of the Criminal Defense and Investigations practice group at Manatt, Phelps & Phillips, LLP. Arunabha Bhoumik is an associate in that group.

It's a common scenario. You're representing the target in a federal securities fraud investigation. The U.S. Attorney's Office in Manhattan is ready to charge your client and the prosecutor asks if your client wants to cut a deal. Exhausted by the lengthy investigation and close to broke, your client wonders: “If I plead guilty, how much time will I get?” While you answer the best you can, you quickly add that only the sentencing judge can say for sure. “Well,” your client asks, “can't we at least pin down the government on its position on sentencing so I know what my likely worst-case scenario is?”

Unfortunately, in most cases you can't provide real comfort for your client. While the government almost certainly will give you an estimate of your client's sentencing exposure as part of the plea process, recent cases in the Second Circuit make clear that the government is unlikely to be bound by that estimate. And, once your client pleads guilty, he likely will be unable to withdraw his plea even if his sentence is much worse than what the government estimated before sentencing. To understand the risks that defendants face, we first need to explain why the government provides sentencing estimates at all.

Background: United States v. Pimentel

In 1991, the Second Circuit discussed the then-emerging problem of criminal defendants being given prison sentences significantly higher than the defendants expected because of the new (and then mandatory) federal Sentencing Guidelines. United States v. Pimentel , 932 F.2d 1029 (2d Cir. 1991). One of the defendants had pled guilty to a drug offense but challenged his sentence because the district court sentenced him based on aggravating evidence adduced at the trial of his co-defendants. The Second Circuit upheld the district court's sentence, but said that it was “quite troubled by the escalating number of appeals” by defendants who pled guilty to crimes but then were surprised by the severity of the sentences imposed on them. The Second Circuit noted that, given its own struggles to date in interpreting the Sentencing Guidelines, it was “not unsympathetic” to claims by defendants who did not fully appreciate the consequences of their pleas. Indeed, the Second Circuit intimated that some variances between the sentence reasonably expected by a defendant and the sentence actually imposed might be so unfair as to raise questions about the validity of the plea itself.

To deal with these concerns, the Second Circuit made a simple suggestion: Before entering into plea agreements, the government, with its “unique expertise in muddling through the complexities of the Guidelines,” could inform defendants of the likely sentencing range following a guilty plea. While the court made clear that the government was not legally obligated to provide such estimates, it nevertheless invited government attorneys to play a role in “helping to ensure that guilty pleas indeed represent intelligent choices by defendants.”

After Pimentel, U.S. Attorneys' Offices within the Second Circuit began providing defendants with so-called “Pimentel letters” as part of the plea process. Although the particular form and content of Pimentel letters has evolved over time, they generally: 1) set forth the government's position regarding the application of the (now advisory) federal sentencing guidelines to the defendant, including an estimate of the applicable guideline range; and 2) reserve the government's right to change its position regarding how the defendant should be sentenced after the plea.

Second Circuit Case Law After Pimentel

Following the Pimentel decision, a body of case law has developed in situations where the government ultimately seeks and obtains a sentence in excess of its Pimentel estimate.

For example, in United States v. Palladino , 347 F.3d 29 (2d Cir. 2003), the Second Circuit held that the government breached a plea agreement when it deviated from its Pimentel estimate. The defendant pled guilty to one count of transmitting a threat in interstate commerce. The plea agreement included a sentencing estimate
“[b]ased on information known to [the government] at this time.” After the plea was entered, but before the defendant was sentenced, the case was reassigned to a different prosecutor, who sought a tougher sentence based on an audio recording of the defendant that had been in the government's possession prior to the plea. The sentencing judge imposed the tougher sentence sought by the government, and the defendant appealed on grounds that the government breached his plea agreement.

The Second Circuit vacated the defendant's plea, holding that because the plea agreement contained a Pimentel estimate explicitly based on information then known to the government, it was “logical for the defendant to believe that the estimate, and the Government's stance at the sentencing hearing, would not be altered in the absence of new information or ' simply because a new Assistant United States Attorney had taken over the case and adopted a different view of the matter.”

In contrast, in United States v. Habbas , 527 F.3d 266 (2d Cir. 2008), the Second Circuit upheld a defendant's sentence even though the government sought a term of imprisonment in excess of its Pimentel estimate based on information known to it at the time of the plea. One of the defendants in Habbas pled guilty to obstructing a federal grand jury investigation. The government provided the defendant with a Pimentel calculation, but the Pre-Sentence Report prepared by the U.S. Probation Office included a recommendation for a longer prison sentence based on a factor that the government knew about, but had simply overlooked, at the time of the plea. At sentencing, the government acknowledged that its failure to account for the additional factor in its Pimentel estimate had been a “mistake” and asked for the longer sentence recommended by the Probation Office. The district court imposed the greater sentence sought by the government.

On appeal, the defendant, relying on Palladino, argued that the longer prison term violated his plea agreement because it was based on information known to the government at the time of his plea agreement. Notwithstanding Palladino, the Second Circuit upheld the defendant's sentence, largely on grounds that there was no evidence that the government had acted “abusively” or in bad faith when it provided its Pimentel guidance. The court explained that, in preparing the Pimentel calculation, the government “simply failed to notice the applicability” of the factor justifying an increased sentence. While recognizing that, “in certain circumstances government deviation from its prior estimate could conceivably produce serious unfairness,” the court nevertheless found that the government's mere failure to “notice the possibility” of a basis for seeking more prison time was not such a circumstance.

Thus, Habbas rejected both a broad reading of Palladino and a categorical rule that the government may deviate from a Pimentel estimate only where newly discovered facts justify the departure. “We think it would be foolhardy to attempt to set a broad rule, beyond noting the obvious importance of good faith on the government's part,” the court explained.

United States v. MacPherson

A recent Second Circuit opinion highlights that court's reluctance to find that a deviation from a Pimentel estimate constitutes a violation of a defendant's plea agreement. United States v. MacPherson , 590 F.3d 215 (2d Cir. 2009). MacPherson pled guilty to one count of conspiring to import narcotics. The Probation Office's Pre-Sentence Report recommended additional prison time based on considerations that were not included in the government's Pimentel calculation. The court imposed a sentence greater than that contemplated in the plea agreement.

While MacPhearson objected to his sentence in the district court, he did not specifically object on grounds that the sentence was inconsistent with the government's Pimentel submission. Thus, on appeal, the Second Circuit reviewed his sentence only for plain error and concluded that the district court's judgment should be upheld. The court noted that in light of the “conflicting outcomes” in Palladino and Habbas, and the fact that the defendant was put on notice in his plea agreement that the Pimentel estimate was non-binding, it was not “plain error” for the district court to impose the higher sentence sought by the government.

In a lengthy concurring opinion, Judge Jon Newman noted that “Palladino and Habbas are problematic, not only for their inconsistency but also for the uncertainty they risk for the use of Pimentel estimates.” Judge Newman would have resolved the “tension” between the two decisions by upholding “all plea agreements with Pimentel estimates, regardless whether the Government at sentencing advocates a higher Guideline range ' as long as the agreement makes clear that the Government is not bound by the estimate” and as long as the district court makes that fact clear during the plea allocution, along with the fact that the defendant will not be able to withdraw his plea if the actual sentence exceeds the Pimentel estimate.

Conclusion

Cases such as Habbas and MacPherson make clear the risk of relying on a Pimentel estimate in assessing the consequences of a guilty plea. A criminal defendant is well advised to take such estimates for what they are ' one piece of information in the sentencing process but not one that can be relied on.

Steven F. Reich ([email protected]), a member of this newsletter's Board of Editors, is co-chair of the Criminal Defense and Investigations practice group at Manatt, Phelps & Phillips, LLP. Arunabha Bhoumik is an associate in that group.