“Prosecutorial Latitude After Stipulated Plea Agreements & the Sadism-Enhancement for Morphed Images” – A Comprehensive Commentary on United States v. Hotaling

1. Introduction

The Second Circuit’s 2025 summary order in United States v. Hotaling, Nos. 24-434(L) & 24-436 (con.), addresses three recurrent sentencing flash-points:

Whether the Government breaches a plea agreement when, at sentencing, it endorses additional Guideline enhancements that were not listed in the parties’ written stipulation;
The correct application of the four-level “sadistic or masochistic conduct” enhancement in U.S.S.G. § 2G2.2(b)(4) to “morphed” child-pornography images; and
When an offender’s destruction of evidence during a supervised-release visit warrants the § 3C1.1 obstruction-of-justice increase for the federal crime of conviction.

Defendant-appellant John Hotaling—already a repeat child-pornography offender—pled guilty to new § 2252A charges and to supervised-release violations. He later argued (i) that the Government had reneged on its plea bargain by supporting a higher offense level in the Presentence Report (PSR), and (ii) that his ultimate 188-month sentence was procedurally and substantively unreasonable.

The panel (Chief Judge Livingston, and Judges Newman & Sullivan) affirmed in full, pronouncing two doctrinal clarifications:

A plea stipulation that lists certain Guideline factors but reserves the Government’s right to “urge the Court” on other issues permits the prosecution to advocate for new enhancements endorsed by Probation. The Government does not breach such an agreement by doing so.
The sadism enhancement under § 2G2.2(b)(4) applies to morphed or computer-generated images when, judged objectively, the depiction would likely inflict pain on a minor participant (here, a pre-pubescent child being vaginally penetrated).

2. Summary of the Judgment

• The Second Circuit affirmed Hotaling’s 188-month sentence and concurrent 12-month revocation sentence.
• No breach of the plea agreement occurred because the written bargain expressly allowed the Government to argue for Guideline findings beyond those stipulated.
• The district court’s adoption of the PSR satisfied procedural-explanation duties, and the sadism (§ 2G2.2(b)(4)) and obstruction (§ 3C1.1) enhancements were applied correctly.
• The sentence—four months below the top of the post-enhancement range—was not “shockingly high” and therefore substantively reasonable.

3. Analysis

3.1 Precedents Cited

The order weaves a robust chain of Second Circuit cases:

United States v. Wilson, 920 F.3d 155 (2d Cir. 2019) – Standard of de-novo review for plea-agreement interpretation.
United States v. Granik, 386 F.3d 404 (2d Cir. 2004) and Altro – Courts must temper contract-law analysis with “special due-process concerns.”
United States v. Lajeunesse, 85 F.4th 679 (2d Cir. 2023) – Ambiguities in plea agreements are construed against the Government.
United States v. Johnson, 93 F.4th 605 (2d Cir. 2024) – Measure of the defendant’s “reasonable expectations.”
United States v. McDermott, 2024 WL 5114132 (2d Cir. 2024) – A near-identical plea clause allowed the Government to argue new enhancements.
United States v. Freeman, 578 F.3d 142 (2d Cir. 2009), Delmarle, 99 F.3d 80 (2d Cir. 1996), and Hotaling (2011) – Collective foundation for applying § 2G2.2(b)(4) to sadistic depictions, including morphed images.
United States v. Ayers, 416 F.3d 131 (2d Cir. 2005) – Obstruction enhancement attaches if the obstructed investigation “plainly encompasses” the federal offense.
United States v. Cavera, 550 F.3d 180 (2d Cir. 2008) (en banc) – Framework for procedural/substantive reasonableness review.

By relying heavily on McDermott (2024) and its own earlier Hotaling (2011) decision, the court reinforced two currents in Second Circuit law: (1) broad prosecutorial latitude so long as the plea text is unambiguous, and (2) a consistent, objective approach to sadism in child-porn cases, irrespective of whether the depicted child is real or computer-generated.

3.2 Legal Reasoning

3.2.1 No Breach of Plea Agreement

• The plea agreement contained the critical sentence: “[The agreement] does not prevent the government from urging the sentencing court to find that a particular offense level, criminal-history category, ground for departure, or guidelines range applies.”
• The court read that reservation literally, invoking contract law but emphasizing fairness: the defendant was on notice that the Government could adopt Probation’s higher calculation.
• The Government’s “estimate” at the change-of-plea colloquy was labelled “just an estimate,” preserving flexibility.
• Accordingly, Hotaling’s “benefit of the bargain” was limited to a promise not to appeal a 120-month sentence—not to a prosecutorial commitment to stay silent on further enhancements.

3.2.2 Procedural Reasonableness

• By formally adopting the PSR, the district court furnished adequate fact-finding (Rainford; Wagner-Dano).
• Sadism (§ 2G2.2(b)(4)): The photo depicted an 11-year-old being vaginally penetrated, an act “likely to cause pain to one so young.” Whether the image was morphed was immaterial (Delmarle; Freeman).
• Obstruction (§ 3C1.1): Destroying a flash drive that held contraband “plainly encompassed” the federal possession offense because both state and federal authorities were examining the same conduct (Ayers).

3.2.3 Substantive Reasonableness

Confronted with a repeat offender, the district court stressed: (i) the need for incapacitation and deterrence, (ii) serial violations of supervision rules, and (iii) actual hands-on molestation revealed during investigation.
The 188-month sentence sat inside the 151–188-month range, and the court said it would have imposed the same term even if lower enhancements applied, rendering any alleged mis-calculation harmless.

3.3 Impact of the Judgment

Plea-Drafting Repercussions – Defense counsel in the Second Circuit must now scrutinize “reservation clauses” more carefully; silence on future enhancements will rarely bind the Government unless the agreement expressly says so.
Child-Pornography Sentencing – The decision cements that morphed or deep-fake images depicting inherently painful conduct trigger § 2G2.2(b)(4), a point increasingly relevant as synthetic media proliferates.
Obstruction Doctrine – Destruction of digital media during a supervised-release inquiry can yield a two-level bump in a later federal indictment arising from the same conduct.
Standard-of-Review Clarity – The panel quietly reaffirmed that a defendant’s failure to raise a breach argument below may be irrelevant if, on de-novo reading, no breach exists; but otherwise plain-error review applies.
Victim-Privacy & Revictimization – The court’s emphasis on “revictimizing” the same minors signals heightened concern for repeat digital exploitation when evaluating § 3553(a).

4. Complex Concepts Simplified

Plea Agreement: A negotiated contract between prosecution and defense that trades a guilty plea for concessions (e.g., charge reduction, sentencing recommendations).
Presentence Report (PSR): Neutral report prepared by U.S. Probation summarizing the offense, defendant’s background, and Guideline calculations; courts may adopt it wholesale.
Offense Level & Enhancements: The Guidelines assign numeric points for the base crime; aggravating factors add “levels,” increasing the sentencing range.
§ 2G2.2(b)(4) – Sadism/Masochism Enhancement: Adds four levels if the material “portrays” sadistic or masochistic conduct—judged by whether the depicted act would cause pain or humiliation if real.
“Morphed” Image: A composite photo where a minor’s face is digitally pasted onto an adult’s body or vice-versa. Courts treat such images as child pornography if they depict sexual activity with an apparent minor.
§ 3C1.1 – Obstruction of Justice: A two-level increase if the defendant willfully impedes investigation/prosecution, e.g., destroying evidence or lying to authorities.
Plain-Error Review: An appellate standard requiring (1) error, (2) that is “plain,” (3) affects substantial rights, and (4) seriously affects the fairness or integrity of judicial proceedings—otherwise, no reversal.

5. Conclusion

United States v. Hotaling underscores two core themes in contemporary federal sentencing. First, unless a plea agreement explicitly muzzles the Government, a prosecutor may champion new Guideline enhancements suggested by Probation without breaching the bargain. Second, the sadism enhancement applies with equal force to computer-altered images when the depicted act would objectively inflict pain on a minor. Together, these holdings fortify prosecutorial discretion at sentencing and push back against attempts to evade higher Guideline exposure through digital manipulation.

Practitioners should read Hotaling as a cautionary tale: negotiated stipulations must be drafted with surgical precision, defendants should anticipate full judicial—and prosecutorial—scrutiny of aggravating facts, and synthetic imagery offers no safe harbor from the harshest child-pornography enhancements. In the larger landscape, the Second Circuit continues to harmonize evolving technology, defendant expectations, and due process into a coherent sentencing jurisprudence that prizes both contractual clarity and victim protection.

“Prosecutorial Latitude After Stipulated Plea Agreements & the Sadism-Enhancement for Morphed Images” – A Commentary on United States v. Hotaling (2d Cir. 2025)