Introduction

In People v. Nestler, 2025 NY Slip Op 05852 (App Div 3d Dept Oct. 23, 2025), the Third Department clarifies and reinforces a pivotal rule of New York plea practice: a sentencing court cannot impose an enhanced sentence beyond a negotiated term based on a defendant’s failure to satisfy a post-plea condition unless that condition—and the consequence of noncompliance—were expressly and objectively stated on the record at the time of the plea, or the defendant is given the opportunity to withdraw the plea before enhancement.

The case arises from a white-collar theft by an attorney from an estate he represented. After accepting a guilty plea to grand larceny in the second degree, the County Court later imposed a harsher sentence (4 to 12 years) when the defendant failed to make restitution prior to sentencing. The Third Department held that because restitution payment by the sentencing date was not an explicit condition of the plea—and because the court gave no notice or withdrawal opportunity—enhancement was unlawful. The appellate court modified the judgment to impose the negotiated 2-to-6-year term and left the restitution order intact.

Case Overview

Court: Appellate Division, Third Department (Lynch, J.; Pritzker, J.P., Reynolds Fitzgerald, Fisher and Mackey, JJ., concurring)

Parties: The People of the State of New York (Respondent) v. Roy K. Nestler (Appellant)

Background: Nestler, an attorney whose license had been suspended and then revoked during the relevant period, stole approximately $512,000 from a client estate. He waived indictment, proceeded by superior court information, and pleaded guilty to grand larceny in the second degree with an agreed-upon sentence of 2 to 6 years’ imprisonment and restitution.

Plea Structure: The County Court rejected the People’s initial offer to permit a plea to grand larceny in the third degree with a 2-to-6-year sentence. Instead, the court accepted a plea to the higher charge (second degree), adjourned sentencing for a year, and stated that full restitution would permit Nestler to withdraw his plea and plead to the reduced felony (third degree). The court suggested that, in the reduced-charge scenario, it would be inclined to include probation.

Critical Fact: Although Nestler was told that restitution could earn him a charge reduction, the record of the plea colloquy did not state that failure to make restitution prior to sentencing would authorize a harsher sentence than the promised 2-to-6-year term. The explicit conditions placed on the promised sentence were limited to appearing for sentencing, not committing new crimes, and cooperating with probation.

Post-Plea: By sentencing, Nestler had paid no restitution. The County Court imposed an enhanced sentence of 4 to 12 years and ordered restitution. Nestler appealed.

Summary of the Opinion

• Challenge to the enhanced sentence survived the appeal waiver and, under the circumstances, did not require preservation via objection or postallocution motion because the enhancement was announced at the end of the proceeding with no practical opportunity to object.
• Under settled law, a court may impose an enhanced sentence only for violation of explicit, objective plea conditions articulated and accepted at the time of the plea, or it must offer the defendant the chance to withdraw the plea before imposing the enhancement.
• Payment of restitution prior to sentencing was not one of the plea’s explicit conditions; it was merely a condition of a potential charge reduction. The record contained no clear finding of a plea-condition violation, and the defendant received no notice that enhancement was under consideration.
• Because no new facts about the underlying crime emerged post-plea, the proper remedy was specific performance of the plea bargain, not merely allowing plea withdrawal. The Third Department modified the judgment to impose the negotiated 2-to-6-year sentence and left the restitution order in place.

Detailed Analysis

Precedents Cited and Their Influence

• Appeal waiver and survival of claim: People v. Lane, 233 AD3d 1207 (3d Dept 2024), lv denied; People v. Hockenbury, 190 AD3d 1155 (3d Dept 2021). These cases support the proposition that a challenge to the legality of an enhanced sentence beyond a negotiated cap survives an appeal waiver. Nestler relies on this to reach the merits notwithstanding an unchallenged waiver of appeal.
• Preservation and opportunity to object: People v. Perry, 235 AD3d 1041 (3d Dept 2025), lv denied; People v. Williams, 27 NY3d 212 (2016); People v. Peque, 22 NY3d 168 (2013), cert denied, 574 US 840 (2014). Williams and Peque recognize that where a sentencing defect is sprung without notice, leaving no practical chance to object, the lack of a contemporaneous objection will not bar appellate review. Nestler squarely fits this exception: the enhancement was announced at the end of sentencing without warning or a finding of any explicit plea-condition breach. The court also notes, in the alternative, it would exercise “interest of justice” jurisdiction even if preservation were required (see People v. Denegar, 130 AD3d 1140 (3d Dept 2015); People v. Tole, 119 AD3d 982 (3d Dept 2014)).
• Enhanced sentencing only for explicit, accepted conditions: People v. Brabant, 229 AD3d 892 (3d Dept 2024); People v. Drayton, 189 AD3d 1892 (3d Dept 2020); People v. Tole, 119 AD3d 982 (3d Dept 2014). These authorities establish two critical constraints: (1) enhancement is permissible upon violation of explicit, objective, on-the-record plea conditions accepted by the defendant; and (2) absent such conditions, a court may not enhance unless it offers the defendant the opportunity to withdraw the plea before imposing the higher sentence. Nestler is a textbook application: restitution was never enumerated as a condition whose breach would authorize enhancement.
• Record at time of plea controls; post-plea communications do not cure: People v. Ackley, 192 AD3d 1203 (3d Dept 2021); People v. Hunter, 173 AD3d 1249 (3d Dept 2019), lv denied 34 NY3d 933 (2019); People v. Denegar, 130 AD3d 1140 (3d Dept 2015). These cases underscore that the defendant must be advised at the plea of the conditions and consequences; later discussions cannot retroactively supply an unstated condition or a warning of enhancement. Nestler rejects the People’s reliance on months-later communications for precisely this reason.
• Specific performance versus plea withdrawal: People v. Jones, 99 AD2d 1 (3d Dept 1984), interpreting the Court of Appeals’ landmark decision in People v. Selikoff, 35 NY2d 227 (1974), cert denied 419 US 1122 (1975); see also People v. Katsafaros, 145 AD3d 1343 (3d Dept 2016), lv denied 29 NY3d 949 (2017); People v. Parker, 271 AD2d 63 (4th Dept 2000), lv denied 95 NY2d 967 (2000). Selikoff and its progeny teach that if, after the plea, the court legitimately learns new information supporting a different sentence, allowing withdrawal of the plea suffices; but where no such new information exists, the court must adhere to its bargain—i.e., specific performance is required. In Nestler, there was no new information about the underlying conduct; the only post-plea development was nonpayment of restitution, which affected a possible charge reduction but did not breach a stated condition of the negotiated sentence.

Legal Reasoning

1. Scope of the bargain and explicit conditions: The record showed two distinct features: (a) a binding promise of a 2-to-6-year sentence on the second-degree larceny plea; and (b) a conditional opportunity to later withdraw that plea and plead to a reduced charge (third degree) upon full restitution, with the court inclined toward a probationary component in that reduced-charge scenario. Crucially, the court’s on-the-record list of conditions attached to the 2-to-6-year promise did not include restitution; it included only appearing for sentencing, remaining arrest-free, and cooperating with probation (see footnote 3).
2. Unlawfulness of enhancement absent notice or withdrawal option: Because payment of restitution by the sentencing date was not an explicit condition of the promised 2-to-6-year sentence, the County Court could not lawfully impose an enhanced 4-to-12-year sentence on that basis. Nor did the court give Nestler notice that enhancement was being contemplated or an opportunity to withdraw his plea before imposing the higher sentence—each independently fatal under Brabant, Drayton, and Tole.
3. Record-bound analysis: The court rejected the People’s reliance on post-plea communications to show Nestler’s understanding that nonpayment would trigger enhancement. The law requires that the conditions and consequences be articulated and accepted at the time of the plea; after-the-fact letters or discussions cannot retrofit the plea with new conditions. The County Court’s own subsequent letter confirmed that restitution was a condition for accessing the reduced-charge track—not a condition of the baseline 2-to-6-year sentence.
4. Preservation and opportunity to object: Though Nestler did not object at sentencing, the enhancement was announced at the close of the proceeding without prior warning, leaving him no practical chance to object. Under Williams and Peque, preservation was unnecessary in these circumstances; the court also signaled that it would exercise interest-of-justice review even if preservation were required.
5. Remedy—specific performance: Applying Selikoff as explained in Jones, the Third Department held that there were no post-plea, newly discovered facts about the crime that could justify altering the sentence. While the nonpayment of restitution had consequences for the conditional charge reduction (i.e., it properly foreclosed the third-degree plea), it did not breach a stated condition of the original plea bargain. Accordingly, the appropriate remedy was to enforce the bargain by imposing the negotiated 2-to-6-year sentence. The appellate court exercised its authority to modify the judgment and impose that sentence directly, while leaving the separate restitution order undisturbed.

Impact and Forward-Looking Significance

• Precision in plea colloquies: Nestler underscores that if a court wishes to condition a promised sentence on pre-sentencing restitution (or any other conduct), the condition and the consequence of violation must be stated explicitly on the record at the plea and accepted by the defendant. Courts that fail to do so risk reversal or appellate modification to the negotiated term.
• Separation of “leniency conditions” from “baseline conditions”: The decision draws a clear line between (a) conditions that merely open an avenue to additional leniency (e.g., permitting a reduced charge upon restitution), and (b) conditions whose breach authorizes a harsher sentence than the negotiated promise. Only the latter must be expressly spelled out at the time of the plea, with an advisement that violation permits enhancement or withdrawal of the plea.
• Record controls; post-plea communications insufficient: Prosecutors and judges cannot rely on letters, off-the-record understandings, or later communications to supply missing plea conditions. Defense counsel should insist that all conditions and enhancement consequences be recited in the allocution.
• Remedial posture—specific performance over remand: Where no new post-plea facts about the underlying offense justify a departure from the plea bargain, appellate courts may directly impose the negotiated sentence rather than remanding. This provides a strong incentive for trial courts to adhere to their bargains absent properly preserved, record-based reasons for deviation.
• Restitution-based dispositions: In white-collar and property cases, courts commonly link restitution to sentencing outcomes. Nestler signals that if restitution nonpayment is to permit enhancement, it must be an explicit, accepted plea condition with clear warnings; otherwise, nonpayment may block a benefit (like a charge reduction) but cannot increase the baseline promised term.
• Appeal waivers and preservation: The decision reaffirms that appeal waivers do not bar challenges to illegal or unpromised sentence enhancements and that lack of preservation will not preclude review when the defendant had no practical ability to object at sentencing.

Complex Concepts Simplified

• Superior Court Information (SCI): A charging instrument filed in a superior court when a defendant waives indictment, allowing felony prosecution without a grand jury indictment.
• Grand Larceny Second vs. Third Degree: In New York, grand larceny in the second degree is a Class C felony (maximum 15 years). Grand larceny in the third degree is a Class D felony (maximum 7 years). The negotiated term here—2 to 6 years—is lawful under either class, but the class matters for collateral and record purposes.
• Enhanced Sentence: A sentence higher than the negotiated or promised term in a plea agreement. Enhancement is lawful only if the defendant has violated an explicit, objective condition stated at the plea or is given a chance to withdraw the plea before enhancement.
• Appeal Waiver: A defendant’s agreement to limit appellate rights as part of a plea. Certain claims, such as an illegal sentence or an unpromised enhancement, generally survive such waivers.
• Preservation / Postallocution Motion: The general requirement to object or move to withdraw a plea to preserve issues for appeal. An exception applies when the defendant has no practical opportunity to object (e.g., when an enhancement is sprung at the end of sentencing).
• Specific Performance vs. Plea Withdrawal (Selikoff framework): If no new, legitimate information arises post-plea to justify changing the sentence, the court must honor the bargain (specific performance). If genuinely new information emerges, the remedy is typically to allow the defendant to withdraw the plea rather than forcing the original sentence.
• Restitution Order and 5% Surcharge: Courts may order restitution to make victims whole, with a statutory 5% collection surcharge. In Nestler, the separate restitution order totaled $540,024 (principal $514,309 plus 5%).

Conclusion

People v. Nestler fortifies a core tenet of New York plea jurisprudence: sentencing enhancements must rest on explicit, on-the-record plea conditions accepted by the defendant, or the defendant must be offered plea withdrawal before enhancement. Nonpayment of restitution before sentencing can foreclose bargained-for leniency (such as a charge reduction), but it cannot justify increasing a promised sentence unless that consequence was clearly articulated at the plea.

The Third Department’s choice of specific performance—imposing the negotiated 2-to-6-year term—reflects the Selikoff rule that, absent new post-plea information about the underlying crime, courts must adhere to their bargains. Practically, Nestler serves as a compliance blueprint: enumerate every condition; state the precise consequence (including potential maximum) for breach; and ensure the defendant expressly accepts those terms at the allocution. Anything less risks reversal or direct appellate imposition of the negotiated sentence.