Waiver of Pretrial Claims After Unconditional Guilty Pleas and Robust Use of Sentencing Cross‑References: Commentary on United States v. Skyfield, No. 24‑2022 (2d Cir. Dec. 9, 2025) (Summary Order)

I. Introduction

United States v. Skyfield is a non‑precedential summary order from the United States Court of Appeals for the Second Circuit, affirming both conviction and sentence in a felon‑in‑possession‑of‑ammunition case under 18 U.S.C. § 922(g)(1). Despite its non‑precedential status under Second Circuit Local Rule 32.1.1, the decision is citable and offers a clear, compact reaffirmation of several recurring principles in federal criminal practice:

The breadth of the waiver of appellate rights that accompanies an unconditional guilty plea.
The strict requirements and limited availability of conditional guilty pleas under Federal Rule of Criminal Procedure 11(a)(2).
The extensive power of sentencing courts to rely on uncharged (or separately charged) conduct, proved by a preponderance of the evidence, to dramatically increase the guideline range through cross‑references such as U.S.S.G. § 2K2.1(c)(1).
The relatively low threshold for the “bodily injury” enhancement under U.S.S.G. § 2B3.1(b)(3)(A).
The high bar defendants face when challenging a within‑Guidelines sentence as substantively unreasonable, even where Probation and the Government had previously suggested lower ranges or recommendations.

The defendant, Tyriek Skyfield, pled guilty to possessing ammunition after a felony conviction. Before that plea, he had moved to dismiss the indictment and to suppress evidence; both motions were denied by the district court (Liman, J.). After the denials, Skyfield sought to enter a conditional guilty plea to preserve appellate review of those rulings, but the Government refused to consent. He then entered an unconditional plea without a plea agreement. The district court found at sentencing, by a preponderance of the evidence, that the ammunition was possessed in connection with a robbery where the victim was grazed by a bullet on the foot and advised by emergency personnel to seek hospital care. Based on this, the court:

Applied U.S.S.G. § 2K2.1(c)(1)’s cross‑reference, sentencing under the robbery guideline (§ 2B3.1) rather than the standalone firearm guideline (§ 2K2.1).
Applied a “bodily injury” enhancement under § 2B3.1(b)(3)(A).
Imposed a 136‑month term of imprisonment, followed by three years of supervised release.

On appeal, Skyfield sought:

Review of the district court’s pretrial rulings despite his unconditional guilty plea, arguing that the Government’s refusal to allow a conditional plea under Rule 11(a)(2) was made in bad faith to block appellate review.
Vacatur or reduction of his sentence as procedurally and substantively unreasonable, challenging:
- The factual finding that the ammunition was possessed in connection with a robbery.
- The application of the bodily‑injury enhancement.
- The length of the sentence as disproportionate.

The Second Circuit (Sack and Pérez, JJ., and district judge Briccetti sitting by designation) rejected all of these arguments and affirmed.

II. Summary of the Opinion

A. Non‑reviewability of Pretrial Motions After Unconditional Guilty Plea

The Court began by reiterating the established rule that by pleading guilty, a defendant generally waives “all non‑jurisdictional defects” in prior proceedings. Relying on United States v. Kukoyi and United States v. Bastian, the panel held that because no recognized exception applied, it lacked authority to review the district court’s denial of Skyfield’s motion to dismiss and motion to suppress.

The panel recognized that Rule 11(a)(2) permits a defendant to reserve issues for appeal through a conditional plea, but only if both the court and the Government consent and the reservation is in writing. Here, the Government refused to consent; Skyfield nonetheless pled guilty without a written conditional plea. Accordingly, the Rule 11(a)(2) exception did not apply.

The Court declined to create a new exception based on alleged governmental bad faith in withholding consent to a conditional plea. It noted that:

Existing Second Circuit precedent does not support such a doctrine (and Skyfield conceded as much).
The only prior exception the Court has recognized in this context relates to potential judicial bias (United States v. Brinkworth), which was not present here.
Petitioner’s allegation of bad faith was “no more than surmise.”
Recognizing bad‑faith refusal to consent as an exception would “create an exception that swallows the rule.”

B. Procedural Reasonableness of the Sentence

On sentencing, the Court applied the familiar abuse‑of‑discretion framework, which incorporates:

De novo review of questions of law, including guideline interpretation (citing United States v. Bonilla, which in turn relies on United States v. Legros).
Clear‑error review of factual findings.

The panel held there was no clear error in the district court’s finding, by a preponderance of the evidence, that Skyfield possessed the ammunition in connection with a robbery. It cited the district court’s reliance on:

Surveillance footage.
Skyfield’s own admission to possessing a shell casing on the day and at the location of the robbery.
Cell‑site location data.
Evidence found on Skyfield’s phone.

Applying standard sentencing practice, the Court reaffirmed that sentencing facts may be found by a preponderance of the evidence, citing United States v. Bellomo.

Based on that factual finding, the district court had used U.S.S.G. § 2K2.1(c)(1), which instructs the court to apply the guideline for a different offense where the defendant used or possessed the firearm or ammunition in connection with another offense. The court therefore applied the robbery guideline, § 2B3.1, rather than sentencing solely under § 2K2.1.

The panel also upheld the district court’s application of the “bodily injury” enhancement, U.S.S.G. § 2B3.1(b)(3)(A). It relied on:

The guidelines’ definition of “bodily injury” in § 1B1.1, cmt. n.1(B), as “any significant injury; e.g., an injury that is painful and obvious, or is of a type for which medical attention ordinarily would be sought.”
The fact that the victim was grazed by a bullet on his foot and emergency medical personnel advised hospital care.
United States v. Markle, which held that injuries warranting medical attention are generally “significant.”
United States v. Spinelli, emphasizing that courts focus on the nature of the injury itself, not merely how medical professionals label it or how the victim subjectively reacts.

The Court rejected the arguments that:

The victim’s initial reluctance to go to the hospital negated bodily injury.
Medical providers’ characterization of the wound as “minor” undermined the enhancement.

C. Substantive Reasonableness of the Sentence

Applying United States v. Cavera, the Court assessed the sentence for substantive reasonableness under the “range of permissible decisions” standard, considering the totality of the circumstances and deferring to the district court’s institutional advantages.

Relying on United States v. Betts and United States v. Fernandez, the panel reiterated that Guidelines sentences are, “in the overwhelming majority of cases,” within the broad range of reasonable sentences. It concluded that this case fell within that typical pattern: the 136‑month sentence was not substantively unreasonable.

The panel also specifically rejected arguments that the sentence was unreasonable merely because:

Probation had recommended a lower sentence.
The Government’s initial range estimate was lower than the ultimate range calculated and applied by the court.

Citing United States v. Messina, United States v. Rivera, and United States v. Eberhard, the Court reaffirmed that:

A district court is not bound by Probation’s recommendation.
It is not bound by the Government’s earlier guideline estimates or recommendations.
Deviations from those non‑binding benchmarks do not, without more, render a sentence substantively unreasonable.

Having rejected all of Skyfield’s arguments, the Court affirmed the judgment of conviction and sentence.

III. Precedents Cited and Their Role in the Decision

A. Waiver via Guilty Plea and Conditional Pleas

United States v. Kukoyi, 126 F.4th 806 (2d Cir. 2025) — Reaffirms that a guilty plea waives all non‑jurisdictional defects in prior proceedings. The panel quotes its footnote (which in turn quotes Bastian) for the general waiver rule. In Skyfield, this principle is decisive: it forecloses appellate review of the suppression and dismissal motions.
United States v. Bastian, 770 F.3d 212 (2d Cir. 2014) — Provides the underlying articulation of the waiver principle adopted in Kukoyi and invoked in Skyfield.
Fed. R. Crim. P. 11(a)(2) — Allows a conditional plea only “with the consent of the court and the government,” and only if the right to appeal specified pretrial motions is reserved in writing. The opinion uses Rule 11(a)(2) to explain why Skyfield’s desire for a conditional plea was legally insufficient without governmental consent.
United States v. Coffin, 76 F.3d 494 (2d Cir. 1996) — Clarifies that to preserve an issue for appeal after a guilty plea, the defendant must (1) obtain the court’s approval and (2) the Government’s consent, and (3) reserve the right in writing. Skyfield relies on this to emphasize that every element of Rule 11(a)(2) is mandatory; lacking government consent, there is no effective conditional plea.
United States v. Brinkworth, 68 F.3d 633 (2d Cir. 1995) — Recognized a narrow exception permitting appeal after a guilty plea where there is a circumstance of potential judicial bias. In Skyfield, the panel cites Brinkworth specifically to cabin that exception to its facts; it refuses to analogize alleged prosecutorial bad faith in blocking a conditional plea to judicial bias.

B. Sentencing Standards and Fact‑Finding

United States v. Bonilla, 618 F.3d 102 (2d Cir. 2010) & United States v. Legros, 529 F.3d 470 (2d Cir. 2008) — Together define the appellate standard of review for sentences: abuse of discretion, incorporating de novo review for legal questions and clear‑error review for factual findings. The Skyfield panel expressly adopts this framework.
United States v. Bellomo, 176 F.3d 580 (2d Cir. 1999) — Affirms that at sentencing, district courts may find facts by a preponderance of the evidence. Skyfield uses this to uphold the finding that the ammunition was possessed in connection with a robbery, which in turn justifies the cross‑reference to the robbery guideline.

C. Guidelines Interpretation: Bodily Injury and Cross‑References

U.S.S.G. § 2K2.1 and § 2K2.1(c)(1) — § 2K2.1 applies to firearm and ammunition offenses such as § 922(g). Subsection (c)(1) contains a cross‑reference directing courts to apply another offense guideline (here, robbery under § 2B3.1) if the defendant used or possessed the firearm or ammunition in connection with another offense. The opinion briefly explains how the district court moved from § 2K2.1 to § 2B3.1 after finding a robbery nexus.
U.S.S.G. § 2B3.1(b)(3)(A) — Provides for a specific offense characteristic enhancement for “bodily injury” to a victim. The Court applies this because the victim was grazed by a bullet and advised to seek hospital treatment.
U.S.S.G. § 1B1.1, cmt. n.1(B) — Defines “bodily injury” for guideline purposes as “any significant injury; e.g., an injury that is painful and obvious, or is of a type for which medical attention ordinarily would be sought.” This definitional note drives the Court’s analysis: the key is whether an “ordinary” victim would seek medical care for such an injury, not whether this particular victim hesitated or whether a provider termed it “minor.”
United States v. Markle, 628 F.3d 58 (2d Cir. 2010) — Holds that injuries that warrant medical attention are generally deemed “significant,” supporting the use of a bodily‑injury enhancement. Skyfield relies on this proposition to emphasize that the need (or recommendation) for medical care is strong evidence that an injury qualifies as “bodily injury” under the Guidelines.
United States v. Spinelli, 352 F.3d 48 (2d Cir. 2003) — Requires courts to focus on the nature of the injury itself, considering pain, obviousness, and whether medical attention would ordinarily be sought, rather than deferring entirely to how medical professionals label the injury. Skyfield cites Spinelli to reject the argument that the providers’ description of the wound as “minor” should control.

D. Substantive Reasonableness and Non‑Binding Recommendations

United States v. Cavera, 550 F.3d 180 (2d Cir. 2008) (en banc) — Sets forth the governing standard for substantive reasonableness: appellate courts must consider the totality of the circumstances, give due deference to district judges, and uphold any sentence within the “range of permissible decisions.” Cavera is the backbone of the panel’s deference in Skyfield.
United States v. Fernandez, 443 F.3d 19 (2d Cir. 2006) & United States v. Betts, 886 F.3d 198 (2d Cir. 2018) — Reinforce that a within‑Guidelines sentence is usually substantively reasonable. The panel quotes Betts, quoting Fernandez, that in the “overwhelming majority of cases,” a Guidelines sentence will be reasonable. This underpins the Court’s comfort with the 136‑month sentence.
United States v. Messina, 806 F.3d 55 (2d Cir. 2015) — Rejects the argument that a sentence is substantively unreasonable merely because it substantially exceeds the Government’s own recommendation. Skyfield invokes Messina to dismiss a parallel argument.
United States v. Rivera, 96 F.3d 41 (2d Cir. 1996) — Holds that a defendant has no justified expectation that Probation’s recommendation will be followed. This is directly applied in Skyfield to negate any reliance on the Probation Office’s lower recommendation.
United States v. Eberhard, 525 F.3d 175 (2d Cir. 2008) — Affirms a sentence that exceeded the Probation Office’s recommendation by 64 months, supporting the principle that divergence from Probation’s recommendation does not by itself show substantive unreasonableness.

IV. Legal Reasoning and Doctrinal Significance

A. Waiver and Conditional Pleas: Government as Gatekeeper

The Court’s reasoning on waiver is tightly anchored in the text of Rule 11(a)(2) and prior circuit precedent. The doctrine operates as follows:

An unconditional guilty plea is treated as an admission of factual guilt and a surrender of all non‑jurisdictional objections to how the case was brought or investigated (e.g., most suppression issues, defects in the indictment, pretrial evidentiary rulings).
A defendant who wishes to preserve appellate review of specific pretrial rulings must obtain a conditional plea that:
- Is entered with both the court’s and the Government’s consent.
- Specifies in writing the precise issues reserved for appeal.
Without government consent, there is no mechanism under Rule 11(a)(2) to force a conditional plea upon the court and Government.
A guilty plea entered without a valid, written, government‑consented condition is treated as unconditional, and the waiver rule fully applies.

In Skyfield, the defense attempted to circumvent this framework by arguing that the Government’s refusal to consent was in bad faith, supposedly aimed at insulating questionable pretrial rulings from appellate scrutiny. The panel’s response is blunt:

There is no doctrinal foundation in the Second Circuit for conditioning the waiver rule on the Government’s motivations in declining to agree to a conditional plea.
The one recognized exception (Brinkworth) is narrowly tied to potential judicial bias, which implicates systemic fairness and structural integrity in a way prosecutorial strategy does not.
The defendant’s “bad faith” assertion is speculative and unsupported by record evidence.
Recognizing an exception whenever a defendant speculates that the Government withheld consent to shield its case from review would make waiver the exception and appellate review the rule — the inverse of the established doctrine.

The opinion thus underscores a critical structural feature of federal plea practice: the prosecution is effectively a gatekeeper to conditional pleas. Defense counsel must assume that absent explicit and documented consent, a guilty plea will waive most appellate issues.

B. Sentencing: Broad Judicial Discretion, Preponderance, and Cross‑References

1. Preponderance Standard at Sentencing

The Court reiterates that, under longstanding Second Circuit law, facts relevant to sentencing enhancements or cross‑references need only be proved by a preponderance of the evidence, not beyond a reasonable doubt. This reflects a line of cases including Bellomo.

In practice, this means that:

The district court could effectively treat the ammunition‑possession conduct as part of a robbery for guideline purposes, even though the conviction itself was for possession of ammunition only.
This can substantially increase the defendant’s offense level and sentencing exposure, as robbery guidelines are typically harsher than firearm possession guidelines.

2. Application of the § 2K2.1(c)(1) Cross‑Reference

Section 2K2.1(c)(1) requires a court to look beyond the offense of conviction if the defendant “used or possessed any firearm or ammunition cited in the offense of conviction in connection with the commission or attempted commission of another offense.” Once that threshold is met, the court applies the guideline for the other offense (here, robbery).

The Second Circuit accepts the district court’s use of this cross‑reference because:

The ammunition in question was tied to a robbery event in time and place.
Multiple evidentiary strands — including surveillance footage, defendant’s admission, cell‑site data, and his phone contents — supported that tie.
The preponderance standard was satisfied; thus, clear‑error review is highly deferential and did not support reversal.

The opinion illustrates the practical power of cross‑references: even when the indictment is limited (e.g., just § 922(g)), sentencing can capture much broader conduct, significantly amplifying punishment.

3. Bodily Injury Enhancement: Objective Nature of the Inquiry

The Court’s handling of the bodily‑injury enhancement is doctrinally important in three ways:

It applies an objective standard: whether the injury is one for which an ordinary person would seek medical attention, whether it is painful and obvious, or both. The actual victim’s preferences or stoicism are not determinative.
It resists attempts to place undue weight on how medical professionals subjectively describe the injury (e.g., “minor”). The guideline commentary and Spinelli direct judges to focus on the injury’s characteristics, not on clinical labels alone.
It recognizes that a bullet graze that prompts emergency responders to recommend hospital care plainly meets the “type for which medical attention ordinarily would be sought” standard, as contemplated by § 1B1.1 cmt. n.1(B) and explained in Markle.

The opinion thus signals that:

Even non‑penetrating gunshot wounds (like a graze) may fairly trigger the bodily‑injury enhancement.
Defendants face an uphill battle in challenging such enhancements when any medical evaluation or recommendation occurs.

C. Substantive Reasonableness: Guidelines as a Strong Anchor

The Court reiterates and applies the core tenets of substantive reasonableness review:

The appellate role is not to decide de novo what sentence it would impose, but to decide whether the sentence chosen by the district court falls within the broad “range of permissible decisions.”
A sentencing court has superior vantage points: direct exposure to the defendant, familiarity with the record, and responsibility for crafting an individualized sentence.
A correctly calculated Guidelines range is typically a strong indicator of reasonableness.

The panel also underscores that neither:

Probation’s recommendation, nor
The Government’s earlier range estimates

are binding. They can inform the district court’s decision, but they do not create enforceable “caps” on reasonableness. Substantial variance from those recommendations does not automatically suggest substantive error, as Messina, Rivera, and Eberhard teach.

V. Impact and Practical Implications

A. For Defense Counsel: Plea Strategy and Issue Preservation

Skyfield reinforces several practical imperatives:

Do not assume conditional pleas are available as of right. The Government has an effective veto under Rule 11(a)(2). Defense counsel must negotiate for conditional pleas and document all conditions in writing.
Warn clients explicitly that an unconditional guilty plea will almost certainly waive the right to challenge pretrial rulings on appeal, including suppression denials and indictment defects.
Recognize that allegations of prosecutorial bad faith in withholding consent to a conditional plea will not, under current Second Circuit law, rescue appellate rights lost via an unconditional plea.
Consider interlocutory strategies carefully in rare situations where pretrial rulings are outcome‑determinative and not easily mooted by a plea.

B. For Sentencing Practice: Robust Use of Relevant Conduct

The decision also has broader sentencing implications:

Cross‑References and Relevant Conduct: Prosecutors and courts can, and do, rely on uncharged or separately charged conduct to apply harsher guideline provisions. For § 922(g) cases, conduct such as robbery, assault, or other violent felonies faced by the same defendant can dramatically increase the range.
Standard of Proof: Because the standard is preponderance, not beyond a reasonable doubt, the evidentiary bar for such enhancements is relatively low. Defense practitioners must aggressively contest the sufficiency and reliability of the evidence put forward to support cross‑references.
Bodily Injury: The threshold for “bodily injury” is not particularly high; bullet grazes and similar injuries, especially when any medical evaluation is recommended or undertaken, will likely trigger enhancements in robbery or assault contexts.
Recommendations versus Authority: Probation reports and even prosecution estimates are advisory. Defense arguments framing substantial upward departures from these as per se unreasonable are unlikely to prevail.

C. Doctrinal Continuity Rather than Innovation

Because this is a summary order, it expressly “do[es] not have precedential effect.” Nonetheless, under Federal Rule of Appellate Procedure 32.1 and Local Rule 32.1.1, it can be cited and will function as persuasive authority. Its significance lies more in:

Clarifying and illustrating existing doctrines, rather than creating new ones.
Demonstrating the Second Circuit’s reluctance to expand exceptions to plea‑based waiver.
Reaffirming lenient evidentiary standards at sentencing for serious enhancements and cross‑references.

VI. Complex Concepts Simplified

A. “Waiver of Non‑Jurisdictional Defects” by Guilty Plea

When a defendant pleads guilty, he generally gives up the right to complain later about most things that happened before the plea, such as:

How evidence was obtained (e.g., search and seizure, Miranda issues).
Defects in the indictment (unless they affect the court’s power to hear the case).
Most procedural rulings (e.g., discovery orders, certain evidentiary rulings).

Only a narrow class of issues survives a guilty plea, mainly:

Questions about whether the court had jurisdiction (i.e., the legal power to hear the case).
Challenges to the voluntariness or intelligence of the plea itself.
Issues explicitly preserved under a valid conditional plea agreement.

B. Conditional vs. Unconditional Guilty Pleas

A conditional guilty plea:

Allows a defendant to plead guilty, but still appeal specified pretrial decisions (e.g., denial of a suppression motion).
Requires written documentation of the issues reserved for appeal.
Requires consent from both the judge and the prosecutor.

An unconditional guilty plea:

Is far more common.
Does not preserve the right to appeal most pretrial rulings.
Results in a broad waiver, as applied in Skyfield.

C. Preponderance of the Evidence vs. Beyond a Reasonable Doubt

Beyond a reasonable doubt is the high standard used at trial to determine guilt. The prosecution must persuade the jury that there is no reasonable doubt about the defendant’s guilt.
Preponderance of the evidence is a lower standard used at sentencing. It means “more likely than not” — if the judge believes there is greater than 50% likelihood that a fact is true, that fact can be used to enhance a sentence.

In Skyfield, the robbery connection and the bodily injury were found by a preponderance of the evidence, which sufficed to justify significant guideline enhancements.

D. Procedural vs. Substantive Reasonableness

Procedural reasonableness asks whether the sentencing process was done correctly:
- Were the Guidelines correctly calculated?
- Did the judge consider the correct factors?
- Did the judge explain the reasons for the sentence?
- Were any important facts clearly misfound or ignored?
Substantive reasonableness asks whether the length and conditions of the sentence are reasonable in light of all the circumstances, not too harsh or too light. The question is not whether the appellate court would have given a different sentence, but whether the sentence is within the broad range a reasonable judge could choose.

In Skyfield, the Court found:

No procedural error in the robbery connection or bodily‑injury findings or in guidelines application.
No substantive unreasonableness, particularly since the sentence was within the Guidelines range.

E. “Bodily Injury” in the Sentencing Guidelines

Under the Guidelines, “bodily injury” is:

Any significant injury; e.g., an injury that is painful and obvious, or is of a type for which medical attention ordinarily would be sought.

This does not require:

Hospitalization.
Permanent damage.
Life‑threatening harm.

It is enough if a significant, painful, or obviously concerning injury occurs, or if a typical person would seek medical care for it. In Skyfield, a bullet graze leading emergency responders to recommend hospital treatment comfortably met this standard.

VII. Conclusion

United States v. Skyfield, while a non‑precedential summary order, offers a pointed reaffirmation of several pillars of federal criminal law and sentencing in the Second Circuit:

An unconditional guilty plea broadly waives the right to challenge prior, non‑jurisdictional rulings on appeal. The only safe harbor is a properly structured conditional plea with explicit government consent and written reservation of issues.
The Court is unwilling to extend limited exceptions like Brinkworth (judicial bias) to alleged prosecutorial bad faith in refusing to authorize a conditional plea. Defendants cannot use claims of bad faith to circumvent the waiver doctrine.
Sentencing continues to rely heavily on relevant conduct proved by a preponderance of the evidence. That conduct can drive:
- Application of cross‑references, such as from firearm possession to robbery.
- Enhancements like “bodily injury,” which need only meet a moderately low threshold.
Bodily injury enhancements are likely to apply in cases of gunfire where even superficial wounds lead to, or would reasonably prompt, medical attention.
Substantive reasonableness review remains highly deferential. A within‑Guidelines sentence, even if substantially above Probation’s or the Government’s initial recommendations, will generally be upheld absent some major misjudgment or reliance on improper factors.

For practitioners, Skyfield is a reminder that the crucial strategic decisions in federal criminal cases — whether and how to plead, what issues to preserve, how to litigate sentencing facts — carry heavy consequences. The decision underscores the Government’s leverage in controlling access to conditional pleas, the judiciary’s extensive discretion in applying sentencing enhancements and cross‑references, and the narrowness of appellate review once a guilty plea is entered and a within‑Guidelines sentence imposed.

Waiver of Pretrial Claims After Unconditional Guilty Pleas and Robust Use of Sentencing Cross‑References: Commentary on United States v. Skyfield (2d Cir. 2025)