Santiago v. Fischer: Second Circuit Requires Admission of “Impediments” Evidence to Prove Causation and Punitive Liability in Earley PRS Cases; Qualified Immunity Remains Unavailable Post-Earley

Introduction

In Santiago v. Fischer, Nos. 23-814(L), 23-855 (2d Cir. Oct. 30, 2025), the Second Circuit clarified critical evidentiary and remedial principles governing damages trials in cases arising from New York’s unlawful, administratively imposed post-release supervision (PRS) terms following Earley v. Murray, 451 F.3d 71 (2d Cir. 2006). The panel (Lynch, Carney, and Menashi, JJ.; opinion by Menashi, J.) held that the district court abused its discretion by barring state defendants from introducing evidence of “legal and administrative impediments” to unilaterally releasing or promptly resentencing Jesus Santiago after Earley. That evidence—showing the practical inability of corrections/parole officials to secure judicial action, the resistance of district attorneys, and the then-uncertain remedial pathways—is highly probative of both causation for compensatory damages and the mental state required for punitive damages.

At the same time, the court reaffirmed that qualified immunity is categorically unavailable to New York corrections and parole officials for post-Earley enforcement of unpronounced PRS, including during 2010, consistent with Betances v. Fischer, 837 F.3d 162 (2d Cir. 2016), Hassell v. Fischer, 879 F.3d 41 (2d Cir. 2018), and Aponte v. Perez, 75 F.4th 49 (2d Cir. 2023). The judgment is therefore:

Reversed insofar as it denied a new trial on the 2007–08 claims (because excluding impediments evidence was error), and
Vacated and remanded insofar as the district court granted summary judgment on the 2010 claims based on qualified immunity (QI), while permitting the defendants to present impediments evidence on causation and damages for that period on remand.

Summary of the Opinion

The panel’s core holdings are:

Evidence of “impediments, legal or otherwise,” to unilaterally releasing a plaintiff from unlawful PRS custody must be admitted because plaintiffs bear the burden to prove causation for compensatory damages and to establish the state of mind necessary for punitive damages. Excluding such evidence improperly relieves plaintiffs of that burden and risks unfair punitive awards.
This evidentiary rule applies not only to compensatory damages (as emphasized in Vincent v. Annucci (Vincent II), 63 F.4th 145 (2d Cir. 2023)) but also to punitive damages, because impediments bear directly on whether any delay reflects “reckless or callous indifference.”
The district court’s exclusion of impediments evidence was not harmless. The jury’s compensatory and punitive determinations could have been “substantially swayed” by hearing why officials believed they needed court action and faced prosecutorial and judicial resistance.
Qualified immunity remains unavailable as a defense to post-Earley enforcement of administratively imposed PRS, including in 2010, under binding Second Circuit precedent. The court vacated the district court’s summary judgment ruling that had insulated defendants from 2010 liability on QI grounds.
On remand, the district court must permit impediments evidence and retry the 2007–08 damages issues; and it must reassess the 2010 claims without QI while allowing defendants to argue that any injury was not caused by their conduct given the impediments.

Case Background

From 2000–2001, Santiago committed state and federal crimes in New York and Virginia. In 2002, he pled guilty in New York to a weapons count with a promised determinate sentence and a five-year PRS term, but at the May 14, 2002 sentencing (before a different judge and without available minutes), “there was no mention of post-release supervision.” After serving federal time, Santiago entered New York custody in 2004; DOCS assumed PRS applied because New York law (Jenna’s Law) mandated it for violent felonies. He was conditionally released in 2004 but violated supervision by moving to Virginia and committing new offenses. Following federal sanction and transfer back to New York in 2007, an ALJ found he violated PRS conditions; he was incarcerated from June 2007 to February 2008.

In April 2008, the New York Court of Appeals (Sparber and Garner) confirmed PRS must be pronounced by a judge in the defendant’s presence; in June 2008, the Legislature authorized DOCS and the Division of Parole (DOP) to trigger court resentencing via Corrections Law § 601-d and Penal Law § 70.85. After further custody in Virginia, Santiago was returned to New York in September 2010; on December 15, 2010, the state court resentenced him without PRS and released him.

Procedural History

2012: Santiago filed a § 1983 action seeking compensatory and punitive damages for unconstitutional PRS enforcement.
2017: On cross-motions, the district court denied QI for post-Earley detention from June 12, 2007 to February 6, 2008, but granted QI for 2010, deeming defendants’ actions objectively reasonable.
2022: At trial, the court excluded defense evidence of impediments (e.g., DA resistance, absence of statutory authority pre-2008, lack of sentencing minutes, state-court refusals). Jury awarded $100,000 compensatory and $750,000 punitive for 2007–08.
Post-trial: The court denied a new trial notwithstanding Vincent II.
Appeal: Defendants challenged exclusion of impediments evidence, the denial of a new trial, and raised QI to preserve it. Santiago cross-appealed the 2010 QI ruling.

Analysis

Precedents Cited and Their Influence

Earley v. Murray, 451 F.3d 71 (2d Cir. 2006). Established that PRS must be pronounced by a judge; administratively imposed PRS is “a nullity.” Directed state to use judicial proceedings to correct sentences. This is the constitutional fulcrum for all subsequent PRS litigation.
Earley (remand), 2007 WL 1288031 (E.D.N.Y.). Stayed habeas relief to allow state resentencing—recognized judicial—not administrative—remedies.
People v. Sparber, 10 N.Y.3d 457 (2008), and Garner v. DOCS, 10 N.Y.3d 358 (2008). New York Court of Appeals held, on statutory grounds, that only sentencing judges may impose PRS, and the remedy is resentencing; did not reach the federal constitutional question.
N.Y. Corr. Law § 601-d; N.Y. Penal Law § 70.85 (2008). Enabled DOCS/DOP to initiate court review/resentencing for defective PRS sentences—legislative response to Earley/Sparber.
Betances v. Fischer (Betances II), 837 F.3d 162 (2d Cir. 2016). Held no qualified immunity for officials who continued to enforce administratively imposed PRS after Earley; emphasized officials “did not take objectively reasonable steps to comply.”
Hassell v. Fischer, 879 F.3d 41 (2d Cir. 2018). Reiterated that officials’ belated remedial steps do not excuse the earlier unreasonable delay; confirmed no QI defense based on later reasonableness.
Vincent v. Annucci (Vincent II), 63 F.4th 145 (2d Cir. 2023). Required plaintiffs to prove causation of damages by showing that, absent the unlawful conduct, their loss would not have occurred. Explicitly required courts to consider “impediments, legal or otherwise,” to release or correction. Santiago extends Vincent II to jury trials and to punitive damages mental state.
Aponte v. Perez, 75 F.4th 49 (2d Cir. 2023). Recognized punitive damages can be based on unexcused delay evidencing callous indifference; Santiago clarifies that impediments are central to determining whether a delay is “unexcused.”
Qualified immunity standards: District of Columbia v. Wesby, 583 U.S. 48 (2018) (clearly established law must put the question beyond debate); Plumhoff v. Rickard, 572 U.S. 765 (2014) (objective reasonableness); McKinney v. City of Middletown, 49 F.4th 730 (2d Cir. 2022) (specific factual context). Santiago reaffirms Second Circuit’s prior holdings denying QI in Earley PRS cases despite factual nuances.
Damages causation and harmless error: Miner v. City of Glens Falls, 999 F.2d 655 (2d Cir. 1993); McCann v. Coughlin, 698 F.2d 112 (2d Cir. 1983); Rentas v. Ruffin, 816 F.3d 214 (2d Cir. 2016); Patterson v. City of Utica, 370 F.3d 322 (2d Cir. 2004); United States v. Paulino, 445 F.3d 211 (2d Cir. 2006); Kotteakos v. United States, 328 U.S. 750 (1946). Santiago leans on these to insist on a counterfactual reconstruction and to find non-harmless error.
Punitive damages: Smith v. Wade, 461 U.S. 30 (1983) (standard); Lee v. Edwards, 101 F.3d 805 (2d Cir. 1996); Kim v. Hurston, 182 F.3d 113 (2d Cir. 1999). Santiago links impediments evidence to the assessment of “reckless or callous indifference.”
Evidence law and hearsay: United States v. Dupree, 706 F.3d 131 (2d Cir. 2013); United States v. Johnson, 117 F.4th 28 (2d Cir. 2024); United States v. Fernandez, 914 F.3d 1105 (7th Cir. 2019). The panel signals that statements by prosecutors and others are admissible for the non-hearsay purpose of showing effect on the listener (state officials’ understanding), thereby reducing Rule 802 obstacles to impediments evidence.

Legal Reasoning

The court proceeds along three tracks: evidentiary error, punitive damages, and qualified immunity.

1) Evidentiary error and causation (Vincent II applied)

Vincent II holds that a plaintiff must prove damages causation by establishing that the injury would not have occurred had officials behaved lawfully, and that courts must consider whether any “impediment, legal or otherwise,” would have prevented unilateral release or correction. Here, the district court excluded evidence directly probative of impediments—DA resistance to resentencing, lack of statutory authority pre-2008, lack of sentencing minutes, state-court refusals, and a widespread belief among DOCS/DOP leaders that court action was necessary. That exclusion:

Relieved the plaintiff of his burden to prove that his incarceration would have ended but for the defendants’ conduct;
Prevented the jury from “reconstruct[ing] what would have occurred had proper procedure been observed;” and
Prejudiced the defense by allowing the plaintiff to argue a simple narrative (“they could have and should have sent him back or released him”) without permitting a factual rejoinder.

On harmless error, the court explains it cannot say with “fair assurance” the verdict was unaffected. A jury could reasonably have found different compensatory and punitive outcomes if it knew that other state actors refused to act and that DOCS/DOP reasonably believed court orders were required.

2) Punitive damages require consideration of impediments

Punitive damages under Smith v. Wade require “evil motive or intent” or “reckless or callous indifference” to federal rights. Aponte permitted juries to infer callousness from an “unexcused” delay in implementing Earley. Santiago’s major contribution is to specify that whether a delay is “unexcused” turns on exactly the sort of impediments the district court excluded:

If officials lacked authority to excise PRS without a judge,
If DAs refused to seek resentencing or courts rejected referrals, and
If records were missing and legal pathways were unsettled,

then a jury might reasonably find the delay reflected attempted compliance in a complex environment rather than “conscious wrongdoing” or callous indifference. Excluding this evidence skewed the punitive analysis in favor of the plaintiff.

3) Qualified immunity

Although defendants argued that Santiago’s case is factually distinct (he was told about PRS during the plea colloquy; officials faced concrete obstacles; later authority suggested court involvement was needed), the court reaffirms that Second Circuit precedent squarely denies QI for post-Earley PRS enforcement:

Earley clearly established that only a judicially pronounced PRS can constrain liberty.
Betances and Hassell hold that officials “did not take objectively reasonable steps” and cannot rely on later remedial actions to excuse earlier violations.
“Efforts made, or not made, by other parties are beside the point for the purposes of determining qualified immunity.” The impediments matter for damages and punitive assessments, not for the QI entitlement.

Applying these cases, the court holds QI is unavailable both for 2007–08 and for 2010. The district court’s 2010 QI grant is vacated, but on remand defendants may still argue that impediments break the chain of causation and limit (or eliminate) damages for that period.

Impact and Forward-Looking Consequences

Santiago v. Fischer is a consequential clarification in the Earley litigation ecosystem. Its impacts include:

Evidentiary practice at trial. Defendants are entitled to introduce robust contextual evidence—communications with prosecutors and courts, records gaps, internal memoranda (e.g., the Governor’s 2008 memorandum), and legislative timing—to show impediments. Objections premised on relevance or hearsay will be harder to sustain when the evidence is offered to show effect on the listener and state of mind, not the truth of third-party statements.
Damages causation rigor. Plaintiffs must prove, and factfinders must determine, what would have happened “but for” the unconstitutional enforcement, explicitly considering whether unilateral release or immediate resentencing was legally and practically possible. This can lead to nominal damages where the same confinement would have occurred anyway, or to reduced compensatory awards that discount periods of delay attributable to genuine impediments.
Punitive damages recalibration. Unadorned evidence of delay may not suffice; plaintiffs should expect to rebut detailed “impediments” narratives if they seek punitive awards. Conversely, defendants can now frame delay as good-faith navigation of legal uncertainty rather than callous indifference.
Qualified immunity unchanged. Santiago solidifies that, notwithstanding impediments, QI remains unavailable for post-Earley enforcement of unpronounced PRS. The line between liability defenses (causation/punitive mental state) and immunity defenses remains bright.
Remedial scope in 2010-era claims. Even when officials acted “reasonably” in the colloquial sense (e.g., promptly initiating § 601-d processes once the inmate was within jurisdiction), those actions do not restore QI; they may, however, defeat or limit damages through a causation analysis that accounts for impediments.
Evidence law guidance. The opinion’s hearsay analysis invites the admission of third-party statements (e.g., DA positions) to prove context and state of mind. Counsel should craft non-hearsay purposes and request appropriate limiting instructions.

Complex Concepts Simplified

Post-Release Supervision (PRS). A period of supervision following completion of a determinate prison term. After Jenna’s Law, certain violent felonies carried mandatory PRS. Earley held that PRS must be pronounced by a judge at sentencing; otherwise, an administratively imposed PRS is void.
Administratively Imposed PRS. When corrections/parole officials add PRS based on statute without a judge pronouncing it at sentencing. Earley forbids this practice; only a judge may impose PRS in the defendant’s presence.
Qualified Immunity (QI). Shields government officials from damages unless they violated clearly established law. In Second Circuit PRS cases, Earley clearly established that PRS must be judicially pronounced; thus, officials who enforced administrative PRS after 2006 cannot claim QI.
Impediments Evidence. Proof that officials faced legal or practical barriers to release or resentencing (e.g., lack of statutory authority pre-2008, resistant prosecutors, adverse court rulings, missing sentencing minutes). It is admissible to show that a plaintiff’s injury was not caused by defendants’ conduct and to negate the mental state for punitive damages.
Punitive Damages. Awarded to punish and deter egregious conduct; require proof of malicious intent or reckless/callous indifference to federal rights. Delay alone does not equal callousness if reasonable impediments explain the delay.
Counterfactual Reconstruction. The factfinder must determine what would have happened if the defendants acted lawfully—e.g., would a court have resentenced promptly? Would the DA have consented? If the answer is “no” or “not sooner,” damages may be reduced or nominal.
Hearsay vs. Effect on Listener. Out-of-court statements offered not for their truth but to show their effect on the listener (the defendants) are not hearsay. In this context, DA statements or court communications are admissible to show why officials believed they lacked authority or faced resistance.

Practice Notes and Litigation Guidance

For defendants:
- Develop a comprehensive “impediments” record: internal emails, policy memoranda, correspondence with DA offices, efforts to obtain sentencing minutes, docket searches, and any judicial responses or refusals.
- Frame third-party statements as non-hearsay “effect on listener” evidence and request limiting instructions.
- Use impediments evidence to challenge causation (compensatory damages) and to negate “reckless or callous indifference” (punitive damages).
- In 2010-era claims, emphasize jurisdictional constraints and the timeline of § 601-d referrals to show that any confinement would have persisted regardless of your conduct.
For plaintiffs:
- Be prepared to prove a workable release/resentencing pathway at the relevant time: identify the court with jurisdiction, show DA willingness (or reasons a court would have acted even without DA consent), and provide evidence that sentencing minutes could be procured or substituted.
- Counter impediments evidence with proof of available alternatives (e.g., earlier § 601-d referrals, emergency motions, or established county-level practices that did result in resentencings).
- For punitive damages, marshal evidence that delays persisted even after impediments dissipated (e.g., post-2008) to support an inference of callousness.
For district courts:
- Admit impediments evidence with careful instructions on its limited purpose, especially for non-hearsay use and state-of-mind relevance.
- Deliver jury instructions that expressly require counterfactual reconstruction and that separate the qualified immunity question (foreclosed) from causation and punitive mental state.
- On summary judgment for 2010 claims, assess whether, even absent the unconstitutional PRS enforcement, confinement would have continued due to unresolved resentencing or independent custody bases.

Unresolved Issues and Remand Tasks

2007–08 period: Conduct a new trial admitting impediments evidence. The jury must decide:
- What portion of Santiago’s confinement would have ended absent the defendants’ unconstitutional conduct?
- Did defendants act with “reckless or callous indifference” warranting punitive damages once impediments are fully considered?
2010 period: Without qualified immunity, the district court may entertain renewed summary judgment motions limited to causation/liability. The central question is whether the defendants’ conduct, given existing impediments and the procedural posture in late 2010, actually caused Santiago’s confinement from September to December 2010.

Conclusion

Santiago v. Fischer meaningfully refines the law governing damages trials in Earley-derived PRS cases. It establishes that defendants are entitled to present evidence of “impediments, legal or otherwise,” and that juries must hear and weigh that evidence when deciding both compensatory causation and punitive liability. The opinion emphasizes that, while qualified immunity remains unavailable to state corrections and parole officials for post-Earley enforcement of unpronounced PRS, impediments can significantly affect outcomes on damages—sometimes reducing awards to nominal or undercutting punitive claims altogether.

The decision harmonizes Vincent II’s causation mandate with Aponte’s punitive standard and Betances/Hassell’s categorical QI holdings, drawing a clear doctrinal line: impediments do not restore immunity, but they do matter—decisively—for what injuries were caused by whom and with what culpable mental state. Going forward, Earley PRS litigation will turn less on abstract liability and more on concrete, context-rich records showing what state officials could realistically do, when they could do it, and what would have happened if they had.