“New York courts were inconsistent in adhering to Earley I’s holding.”
How later courts described this case
- “New York courts were inconsistent in adhering to Earley I’s holding.”
- “Having resolved this issue on statutory grounds, we need not reach petitioner’s constitutional arguments and decline to do so. Neither do we pass on the applicability of Earley.”
- “Neither prior to the entry of his guilty plea nor at his sentencing was [Earley] informed that he 26 was subject to a term of PRS, and his commitment order did not refer to PRS conditions.”
- explaining that a court order may be introduced when “the significance of the Order lies in the fact that it issued”
Written by the judges who cited it.
The opinion
No. 23-814(L)
Santiago v. Fischer
In the
United States Court of Appeals
FOR THE SECOND CIRCUIT
AUGUST TERM 2023
Nos. 23-814(L), 23-855
JESUS SANTIAGO,
Plaintiff-Appellee-Cross-Appellant,
v.
BRIAN FISCHER, individually and as Commissioner of the New
York State Department of Corrections and Community
Supervision, ANTHONY J. ANNUCCI, individually and as Deputy
Commissioner of and Counsel to the New York State Department
of Correctional Services, TERRENCE X. TRACY, individually and as
Chief Counsel to the Division of Parole,
Defendants-Appellants-Cross-Appellees. *
On Appeal from the United States District Court
for the Eastern District of New York
ARGUED: JUNE 18, 2024
DECIDED: OCTOBER 30, 2025
* The Clerk of Court is directed to amend the caption as set forth above.
Before: LYNCH, CARNEY, and MENASHI, Circuit Judges.
Plaintiff Jesus Santiago claimed that state officials violated his
constitutional rights by enforcing terms of his post-release
supervision that our court ruled unconstitutional in Earley v. Murray,
451 F.3d 71 (2d Cir. 2006). At trial, the defendants sought to introduce
evidence that legal and administrative impediments prevented the
resentencing of Santiago and correspondingly reduced the liability of
the defendants for failing to achieve the resentencing. The district
court barred the evidence on the grounds that it would confuse the
jury and had limited probative value. After the jury returned a verdict
awarding Santiago $100,000 in compensatory damages and $750,000
in punitive damages, the defendants moved for a new trial. The
district court denied the motion. We hold that the district court
abused its discretion by barring the evidence of impediments and
therefore erred by denying the motion for a new trial. We reverse the
judgment of the district court insofar as it denied the motion for a new
trial related to Santiago’s incarceration in 2007-08. At the same time,
we conclude that our precedents require the denial of qualified
immunity as to both the 2007-08 period and the period of
incarceration in 2010. We vacate and remand insofar as the district
court dismissed the claims related to the incarceration in 2010 on
summary judgment. We remand for further proceedings consistent
with this opinion.
BLAIR J. GREENWALD, Assistant Solicitor General
(Barbara D. Underwood, Solicitor General, Andrea Oser,
Deputy Solicitor General, on the brief), for Letitia James,
Attorney General of the State of New York, New York,
NY, for Defendants-Appellants-Cross-Appellees.
2
ROB RICKNER, Rickner PLLC, New York, NY, for Plaintiff-
Appellee-Cross-Appellant.
MENASHI, Circuit Judge:
From 2000 to 2001, Jesus Santiago committed several state and
federal felonies in New York and Virginia. After serving his term in
prison, Santiago began to serve his state and federal terms of post-
release supervision. Santiago repeatedly violated the terms of that
supervision and, accordingly, was repeatedly reincarcerated.
In 2006, we held that the rules for post-release supervision in
New York violated the constitutional rights of some criminal
defendants. See Earley v. Murray, 451 F.3d 71, 76 (2d Cir. 2006). 1 We
ordered New York to remedy the constitutional violations but offered
limited guidance about how to do so. In 2008, the state legislature
responded to our ruling by authorizing corrections officials to initiate
resentencing proceedings in order to re-impose terms of post-release
supervision. After those changes were implemented, the defendants
initiated a resentencing proceeding for Santiago in 2010. But from
June 2007 to February 2008, Santiago had been incarcerated for
violating the terms of his post-release supervision. Santiago sued for
compensatory and punitive damages on the ground that he had been
incarcerated in violation of his constitutional rights.
The district court dismissed the complaint insofar as it sought
damages for incarceration from September to December 2010 because
the defendants acted reasonably at that time. But the district court
1 We refer to this decision as Earley or Earley I.
3
allowed the claims for damages related to the incarceration in 2007-
08 to proceed to trial.
At trial, the defendants sought to introduce evidence that legal
and administrative impediments prevented the defendants from
unilaterally initiating a resentencing proceeding for Santiago during
that period. The district court barred the evidence on the ground that
it would confuse and prejudice the jury. After the jury returned a
verdict awarding Santiago $100,000 in compensatory damages and
$750,000 in punitive damages, the defendants moved for a new trial.
The district court denied the motion, and the defendants now appeal.
Santiago cross-appeals the dismissal of his claims related to his
incarceration from September to December 2010.
We hold that the district court abused its discretion by barring
the evidence of impediments and therefore erred by denying the
motion for a new trial. We reverse the judgment of the district court
insofar as it denied the motion for a new trial related to the 2007-08
period. At the same time, we conclude that our precedents require the
denial of qualified immunity as to both the 2007-08 and 2010 periods.
Accordingly, we vacate the judgment of the district court insofar as it
dismissed the claims related to incarceration in 2010 on the basis of
qualified immunity. We remand for further proceedings consistent
with this opinion.
BACKGROUND
In January 2000, Santiago shot someone in the leg with a
handgun in Brooklyn, New York. He was indicted in state court—in
the Kings County Supreme Court in Brooklyn—for two counts of
assault, two counts of criminal possession of a weapon, and one count
of criminal possession of a loaded firearm. After Santiago was
released on bond pending a criminal trial, he fled New York.
4
A year and a half later, Santiago was arrested in Virginia on
separate federal charges and indicted in the U.S. District Court for the
Eastern District of Virginia. In November 2001, he pleaded guilty to
possession of crack cocaine with intent to distribute and was
sentenced to thirty-seven months of imprisonment and four years of
supervised release. The conditions of Santiago’s federal supervised
release required him to report regularly to his federal probation
officer and to submit to drug testing. 2
While incarcerated in December 2001, Santiago sent a letter to
the state court in New York to resolve his pending charges from the
Brooklyn shooting. Santiago was transferred from federal custody in
Virginia to state custody in New York in January 2002.
I
On May 3, 2002, Santiago—while still serving his federal
sentence—pleaded guilty in state court before Justice Sheldon
Greenberg to one count of criminal possession of a weapon. Justice
Greenberg explained during the hearing that Santiago was pleading
guilty “in exchange for” the “promise” of the state court to sentence
Santiago to (1) the minimum determinate term for a Class C violent
felony of three and a half years of imprisonment to run concurrently
with his federal sentence from January 2, 2002, and (2) the “five-year
post-release supervision time that will be imposed on a Class C
felony.” J. App’x 352-53. As part of this arrangement, the terms of
Santiago’s federal supervised release would later be modified to
require that he remain in New York State.
2 See Minute Entry, United States v. Santiago, No. 01-CR-251 (E.D. Va. Nov.
16, 2001) (sentencing hearing).
5
A
Justice Greenberg asked if this arrangement reflected what
Santiago “want[ed] to do,” and Santiago replied “[y]es.” Id. at 353.
Santiago reiterated his understanding of and agreement with the
terms of the plea agreement several times during allocution. See id. at
353-59. The Kings County District Attorney’s Office also agreed to the
plea and to the sentence. See id. at 359-60. After allocution, Santiago
asked Justice Greenberg to impose the sentence immediately. Justice
Greenberg stated that he could not do so until the court received the
presentence report. Justice Greenberg scheduled the sentencing
hearing for two weeks later.
Unfortunately, Justice Greenberg was unavailable on the
scheduled date because of a car accident. So on May 14, 2002, a
sentencing hearing was held before Justice Gustin Reichbach. The
defendants have not been able to locate the minutes or a transcript
from the sentencing hearing, but the parties stipulated at trial that at
the hearing Santiago received a term of imprisonment of three and a
half years but “there was no mention of post-release supervision.” Id.
at 614-15.
After sentencing, a court clerk filled out a form titled “Sentence
and Order of Commitment” reporting the results of the sentencing
hearing. The clerk recorded the term of imprisonment of three and a
half years running concurrently with the federal sentence from
January 2, 2002. The form did not include a section to record a term
of post-release supervision, and the clerk did not separately write a
term of post-release supervision in the margin.
B
In April 2004, Santiago was released from federal custody and
transferred to the custody of the New York State Department of
6
Correctional Services (“DOCS”) to serve the rest of his concurrent
state sentence of imprisonment. 3 The DOCS calculated the remaining
period of imprisonment on his state sentence, set to expire on May 29,
2005. The DOCS assumed that the state court had imposed the post-
release supervision term because that term was required by then-
binding New York law.
The term of post-release supervision had been required since
1998, when the state legislature reformed the sentencing framework
applicable to violent felons. See Ch. 1, §§ 4, 15, 1998 N.Y. Laws 1, 2, 5-
6. Under the reformed rules, violent felons received a determinate
sentence followed by a mandatory period of post-release supervision.
See People v. Catu, 4 N.Y.3d 242, 244 (2005). The 1998 reform eliminated
the prior practice of imposing an indeterminate sentence with a
maximum period of incarceration and a parole-eligibility date. The
legislature instead required courts, in most cases, to impose a fixed
sentence for a definite period established by statute followed by a
fixed period of post-release supervision. See N.Y. Penal L. § 70.00(6).
C
On November 5, 2004, Santiago was conditionally released
from state prison seven months early. Under New York law, when
someone is conditionally released from prison, the remaining portion
of his prison term is “held in abeyance.” N.Y. Penal L. §§ 70.40(2),
70.45(5)(a). If the person then violates the conditions of his
supervision, he receives no credit against the sentence until he is
reincarcerated or restored to supervision. See id. §§ 70.40(3)(b),
3 In 2011, the DOCS and the Division of Parole (“DOP”) merged to form
the Department of Corrections and Community Supervision. See People v.
Brown, 25 N.Y.3d 247, 249 (2015). We refer in this opinion to the entities that
existed at the relevant time.
7
70.45(5)(d). For that reason, seven months of Santiago’s term of
imprisonment was held in abeyance while he served what the DOCS
believed was his mandatory term of post-release supervision.
While Santiago was serving his state-mandated post-release
supervision, he was simultaneously serving a federal term of
supervised release based on his 2001 conviction. Both his state term
of post-release supervision and his federal term of supervised release
required him to report to a probation officer, to submit to drug testing,
and to remain in New York State. But within the next year, Santiago
moved to Virginia in violation of the conditions of both sentences.
D
On October 30, 2005, local authorities in Virginia arrested
Santiago on charges involving the brandishing of a firearm and
possession of marijuana. Santiago was released from local custody in
Virginia on November 17, 2005. It appears that neither federal nor
New York authorities were notified of the arrest or the release.
But almost a year later in October 2006, federal authorities in
Virginia arrested Santiago again. 4 As part of the ensuing
proceedings, the U.S. District Court for the Eastern District of Virginia
determined that Santiago had violated the terms of his federal
supervision and sentenced him to eight months of imprisonment
followed by thirty additional months of supervised release.
After completing the new term of federal incarceration,
Santiago was transferred to New York on June 12, 2007. He was
charged with violating the conditions of his state post-release
supervision by absconding to Virginia and committing new crimes in
4See Marshal’s Return on Warrant for Arrest, United States v. Santiago,
No. 01-CR-251 (E.D. Va. Oct. 25, 2006), ECF No. 42.
8
2005 and 2006. Following a hearing, a state administrative law judge
sustained the charges and ordered that Santiago return to the custody
of the DOCS to be incarcerated until February 2, 2008. See J. App’x
113, 148, 616-17.
E
On February 1, 2008, Santiago was released from state prison. 5
But he remained subject to federal supervised release and to state
post-release supervision. See J. App’x 617. As before, the conditions of
both forms of supervision barred him from leaving New York State.
But by February 6—only a few days after his release from state
prison—Santiago had again left for Virginia in violation of those
conditions.
Two months later, Virginia authorities arrested Santiago for the
2005 offenses involving the brandishing of a firearm and possession
of marijuana. Santiago pleaded guilty to possession of marijuana with
intent to distribute and was sentenced in a Virginia state court to ten
years of imprisonment with eight years suspended on the condition
that he serve one year of supervised probation.
While serving that sentence in June 2008, Santiago appeared
before the U.S. District Court for the Eastern District of Virginia to
address charges regarding his violation of the conditions of the
federal term of supervised release that began when Santiago left New
York state prison in February 2008. The district court determined that
Santiago violated the terms of supervised release and sentenced him
5 Because February 2, 2008, was a Saturday, Santiago was released on
February 1. See N.Y. Corr. L. § 500-l (“When the date of release … falls on
Saturday or Sunday, it shall be deemed to fall on the preceding Friday.”).
9
to seven months of imprisonment and two further years of supervised
release.
II
In September 2010, Santiago was released from federal prison
in Virginia, and he was transferred back to New York on charges of
violating the conditions of his state post-release supervision in
February 2008. But the law applicable to mandatory post-release
supervision in New York had changed while Santiago was
incarcerated.
A
In 2006, this court held that the Due Process Clause of the U.S.
Constitution requires a state court that imposes a determinate
sentence of incarceration on a defendant to make a separate oral
pronouncement of any term of post-release supervision, even if the
term is statutorily required. See Earley, 451 F.3d at 75-76. If the state
court does not orally pronounce the term of post-release supervision,
it “is a nullity.” Id. at 76. Recognizing that this holding could cause
substantial disruption, our court emphasized that “[o]ur ruling is not
intended to preclude the state from moving in the New York courts
to modify” a defendant’s “sentence to include the mandatory PRS
term.” Id. at 77. We explained that when the DOCS has “discovered
the oversight” of a lack of oral pronouncement of the mandatory term
of post-release supervision, “the proper course would [be] to inform
the state of the problem, not to modify the sentence unilaterally. The
state then could [move] to correct the sentence through a judicial
proceeding, in the defendant’s presence, before a court of competent
jurisdiction.” Id. at 76. Based on these instructions, the district court
on remand in Earley stayed the grant of habeas relief “to permit the
sentencing court to exercise its power to conform the sentence to the
10
mandate of New York law.” Earley v. Murray, No. 03-CV-3104,
2007 WL 1288031, at *3 (E.D.N.Y. May 1, 2007).
The Earley decision called into question the sentences of
thousands of defendants whose terms of post-release supervision
may not have been orally pronounced at sentencing. See J. App’x 562-
63. At the time, however, the remedy that Earley identified—a
resentencing that would cure the initial failure to pronounce the
mandatory term of post-release supervision under state law—could
be initiated only by the courts, state prosecutors, and defendants.
State corrections officials had no authority to refer cases to state court
for resentencing.
And state prosecutors were not always willing to make the
referrals. The Earley decision “was ‘met with resistance at the state
level,’ and many officials and offices failed to take action to address
the many offenders subjected to administratively imposed PRS.”
Santiago v. Cuomo, No. 12-CV-2137, 2019 WL 8587292, at *3 (E.D.N.Y.
Sept. 23, 2019) (quoting Betances v. Fischer, 837 F.3d 162, 166 (2d Cir.
2016)). 6 “The Kings County District Attorney remained similarly
resistant to addressing this issue, filing briefs challenging the notion
that individuals … were entitled to have the administrative PRS
component of their sentence stricken.” Id. Claims by individual
defendants in state court often failed because the state courts decided
that the DOP was required to enforce the mandatory term of post-
release supervision despite Earley. 7 State courts also denied requests
6 We refer to the Betances decision as Betances or Betances II.
7 See, e.g., People ex rel. Joyner v. DOP, No. 75045, 2007 WL 1345702, at *5-6
(N.Y. Sup. Ct. May 8, 2007) (“[T]he Division of Parole would itself be in
violation of the law if it did not enforce the statute mandating post-release
supervision and supervise all violent felony offenders following their
release from state prison, as ‘Jenna’s Law’ requires. Every judgment of
11
by the DOCS and the DOP to refer defendants to the relevant
sentencing courts for resentencing. 8 The DOCS and the DOP even
“filed a declaratory judgment action in state court seeking judicial
approval of a plan that would permit state agencies, district attorneys,
and state courts to systematically identify and refer improperly
sentenced inmates back to the sentencing courts to be resentenced.”
Betances, 837 F.3d at 170. “The state court, however, did not grant the
injunctive relief sought by DOCS and DOP.” Id.
In April 2008, the New York Court of Appeals held that state
statutes required the oral pronouncement of a mandatory term of
post-release supervision in the presence of a defendant. See People v.
Sparber, 10 N.Y.3d 457, 469-71 (2008); Garner v. DOCS, 10 N.Y.3d 358,
362 (2008) (“[T]he sentencing judge—and only the sentencing judge—
is authorized to pronounce the PRS component of a defendant’s
conviction for a second violent felony offense includes a discretionary
period of determinate incarceration, within a minimum and maximum
range set by the legislature, and a mandatory five year period of post-
release supervision. In these cases, the judgments of conviction included
both the incarceratory periods actually pronounced, and the five year
period of post-release supervision period mandated by law. Since that is
the law, habeas corpus release is entirely inappropriate.”); Betances, 837 F.3d
at 166 (“New York courts were inconsistent in adhering to Earley I’s
holding.”) (citing cases).
8 See J. App’x 195-96 (“Although DOCS and Parole asked Article 70 and 78
courts to refer PRS matters to the sentencing courts, such courts rarely
granted such applications. Indeed, in the habeas proceeding brought in the
Bronx County Supreme Court by a named plaintiff in the Betances class
action pending in the Southern District of New York, the Bronx County
Supreme Court denied the application of Parole to transfer the matter to the
criminal court, and in declining to refer the proceedings, stated that the
court did not have the authority to transfer petitioner to the criminal court
in order to resolve the PRS issues.”).
12
sentence.”). 9 The Court of Appeals explained that “[t]he sole remedy
for a procedural error such as this is to vacate the sentence and remit
for a resentencing hearing so that the trial judge can make the
required pronouncement.” Sparber, 10 N.Y.3d at 471.
In June 2008, the state legislature authorized the DOCS and
the DOP to refer defendants to state courts for resentencing. See
Ch. 141, § 5, 2008 N.Y. Laws 3168, 3169-70 (codified at N.Y. Corr. L.
§ 601-d). The new statutory procedure allowed the DOCS and the
DOP to notify state courts and defendants about potentially
unpronounced terms of post-release supervision and thereby to
trigger remedial proceedings. If the state court determined that the
term of post-release supervision had been pronounced, the state court
was required to issue a superseding commitment order and
accompanying decision confirming as much. If the state court
determined that the term may not have been pronounced, the state
court would convene a resentencing proceeding with the
prosecutor and the defendant at which the defendant could be
properly sentenced with or without the otherwise mandatory term
of post-release supervision. See N.Y. Corr. L. § 601-d(2)-(5); N.Y. Penal
L. § 70.85.
9 The New York Court of Appeals did not address whether that
pronouncement was constitutionally required. See Sparber, 10 N.Y.3d at
471 n.5 (“Because defendants are entitled to relief under the CPL, we need
not reach their constitutional claims, which rely primarily upon the Second
Circuit’s decision in Earley.”); Garner, 10 N.Y.3d at 363 (“Having resolved
this issue on statutory grounds, we need not reach petitioner’s
constitutional arguments and decline to do so. Neither do we pass on the
applicability of Earley.”) (citations omitted).
13
B
Based on the new legislation, the DOP referred Santiago to the
state court in 2010 to determine whether the term of post-release
supervision should remain in force after he was transferred back to
New York. On December 15, 2010, Santiago and the Kings County
District Attorney’s Office appeared before Judge Reichbach. Santiago
sought resentencing without a term of post-release supervision, and
the District Attorney’s Office consented to that resentencing. See
J. App’x 608. Based on that agreement, Judge Reichbach orally
resentenced Santiago without a term of post-release supervision and
issued a written order to that effect. See id. at 605. Santiago was then
released.
PROCEDURAL HISTORY
This civil case began in May 2012 when Santiago sued state
corrections officers for violating his rights under 42 U.S.C. § 1983.
Santiago sought compensatory and punitive damages for the
purported constitutional violation of enforcing a term of post-release
supervision that was not pronounced by the state court at his
sentencing in 2002.
I
In 2017, the parties cross-moved for summary judgment.10 The
district court denied summary judgment to those defendants whom
10 In May 2012, Santiago was sentenced by the federal district court to nine
months of imprisonment for violating the terms of his federal term of
supervised release. See Minute Entry, United States v. Santiago, No. 01-CR-
251 (E.D. Va. May 17, 2012), ECF No. 71. In November 2012, Santiago was
charged in a Virginia state court with additional crimes. He pleaded guilty
to issuing a bomb threat and to assault. Santiago was incarcerated in
Virginia until May 2015.
14
it determined were personally involved in the alleged constitutional
deprivation: the commissioner of the New York State Department of
Corrections and Community Supervision, the deputy commissioner
of the DOCS, and the chief counsel of the DOP. The district court held
that these defendants were entitled to qualified immunity for the
period preceding the Earley decision in 2006 and before June 12, 2007,
because Santiago “was not in New York State custody, and would not
have been available for a resentencing proceeding.” Santiago v. Cuomo,
No. 12-CV-2137, 2017 WL 11929991, at *10 (E.D.N.Y. Sept. 30, 2017).
The district court decided that these defendants were not
entitled to qualified immunity, however, for the period following
Earley in which Santiago was in New York State custody and his term
of post-release supervision was enforced. That period began on June
12, 2007, and ended when Santiago fled New York on February 6,
2008. And the district court decided that the defendants were entitled
to qualified immunity again for the period that followed Santiago’s
transfer to New York in September 2010 because at that point the
defendants took prompt and objectively reasonable steps to refer him
to state court for resentencing.
A
The district court scheduled a trial on the remaining claims. In
pretrial motions in limine filed in July 2022, the defendants asked the
district court to permit the introduction of evidence of how state law,
state prosecutors, and state courts obstructed the defendants from
releasing Santiago before February 2008. The defendants also moved
to adjourn the trial pending decisions from our court that would
address the propriety of introducing such evidence. See Vincent v.
Annucci (Vincent II), 63 F.4th 145 (2d Cir. 2023); Aponte v. Perez,
75 F.4th 49 (2d Cir. 2023).
15
The district court held a status conference in October 2022 at
which it stated that it would not allow the evidence of impediments
to Santiago’s release to be presented at trial. The district court
believed that the evidence was irrelevant because the jury would not
decide the issue of causation but only the amount of damages to be
awarded. The district court explained that the “jury will hear” that
“nobody sent [Santiago] back for resentencing” after Earley and that
“[t]he people who could have sent him back for resentencing are the
three defendants who had custody of him and should have done it,
and they didn’t. It’s very simple.” J. App’x 474.
B
The district court reiterated its decision in November 2022,
stating that it would reject the defendants’ attempt to introduce
evidence of impediments even if the evidence were proffered solely
to explain the defendants’ subjective understanding that they lacked
the authority to release Santiago without judicial intervention. See id.
at 480-81. The defendants argued that the district court should admit
evidence of their understanding of state law and the practices of state
officials at least in the context of determining whether the defendants
had the requisite intent for an award of punitive damages. The district
court agreed to permit additional briefing on that issue.
With the supplemental briefing, the defendants submitted a
2008 memorandum of the governor explaining that the participation
of state courts was “crucially important” for the DOCS and the DOP
in addressing the need for resentencing. 11 The memorandum
11 Defendants’ Supplemental Memorandum of Law in Response to the
Court’s Request for Further Briefing on the Relevance of Penal Law § 70.45
to Punitive Damages, Exhibit A, at 4, Santiago v. Cuomo, No. 12-CV-2137
(E.D.N.Y. Nov. 21, 2022), ECF No. 198-1.
16
acknowledged that in many cases “the absence of sentencing
minutes” would make it “impossible” for the DOCS and the DOP “to
know whether PRS was properly imposed at the time of sentence”
and that “[s]uch matters are appropriate for judicial resolution.”
J. App’x 493.
The district court decided that the defendants could not
introduce evidence of their understanding that they lacked the legal
authority to release Santiago or to refer him to the state courts.
See Santiago v. Fischer, No. 12-CV-2137, 2022 WL 17227673, at *1
(E.D.N.Y. Nov. 25, 2022). The district court reasoned that the
admission of such evidence could confuse the jury and that the risk of
confusion outweighed any probative value because the “[d]efendants’
liability (including causation) for their unconstitutional conduct has
not only been extensively litigated, but also repeatedly determined by
the Second Circuit.” Id. at *3.
II
The case was tried to a jury in November 2022. The jury did not
hear the proposed evidence regarding the defendants’ understanding
of state law. Nor did the jury hear that state prosecutors, state courts,
or state law might have impeded the defendants from addressing
Santiago’s unpronounced term of post-release supervision. The jury
heard that the defendants imposed an unlawful term of post-release
supervision and did not release Santiago or refer him to a state court
between June 2007 and February 2008 to address his sentence. See, e.g.,
J. App’x 531, 534, 554, 563.
In closing, counsel for Santiago emphasized that the defendants
could have referred Santiago for resentencing or released him
immediately after Earley. See id. at 586-88, 593-94. The defendants
could not respond to the argument with evidence of the impediments
17
to doing so. See id. at 589-93. The jury awarded Santiago $100,000 in
compensatory damages and $750,000 in punitive damages.
III
The defendants filed a renewed motion for judgment as a
matter of law or, alternatively, for a new trial. While that motion was
pending, our court decided Vincent II. In supplemental briefing, the
defendants argued that a new trial was warranted in light of Vincent II
because, just as in that case, the district court here had prohibited the
defendants from testifying about impediments to releasing Santiago
after Earley. As a result, Santiago had been improperly relieved of the
burden of proving causation.
The district court denied the motion. The district court
concluded that Vincent II did not require a new trial because the
defendants had “testified to their understanding, experiences, and
perceived obstacles to complying with Earley I, and the steps they
took specifically with respect to Santiago’s illegal PRS sentence.”
Santiago v. Fischer, No. 12-CV-2137, 2023 WL 2974201, at *6 (E.D.N.Y.
Apr. 16, 2023). The defendants testified, for example, “about the
logistical process and perceived impediments in acting expeditiously
in response to Earley, including that they believed they needed a court
order to excise a sentence, the lack of complete records such as
individuals’ sentencing minutes, their efforts to create a
comprehensive database of the illegal PRS sentences, and their efforts
to organize and disseminate that information to county officials.” Id.
at *21 (citations omitted).
The district court rejected the challenge to the award of
punitive damages because, “[b]ased on evidence at trial, the jury
decided whether Defendants’ unreasonable delay in complying with
Earley I constituted callous and reckless disregard of Plaintiff’s
18
constitutional rights and caused his injuries.” Id. at *10. The district
court emphasized that the testimony the defendants managed to offer
“about Jenna’s Law was of marginal relevance in explaining why they
disregarded the mandates of Earley I, and also risked juror
confusion.” Id. at *19.
DISCUSSION
The defendants argue that the district court abused its
discretion by excluding evidence of impediments and by denying the
motion for a new trial with respect to the 2007-08 period. See
Appellants’ Br. 40-48. The defendants emphasize that the exclusion of
that evidence prejudiced the defense, particularly with respect to the
award of punitive damages. See id. at 49-51. The defendants also
challenge the denial of qualified immunity with respect to the 2007-
08 period. See id. at 52-55. Meanwhile, Santiago argues that the district
court erred in holding that the defendants acted reasonably in 2010
and could not be liable for damages for his incarceration from
September to December 2010. See Appellee’s Br. 47-48.
I
We review for abuse of discretion a district court’s evidentiary
rulings and denial of a motion for a new trial. See United States v.
Miller, 626 F.3d 682, 687-88 (2d Cir. 2010); Kosmynka v. Polaris Indus.,
Inc., 462 F.3d 74, 82 (2d Cir. 2006). A district court abuses its discretion
when “its decision rests on an error of law (such as application of the
wrong legal principle).” United States v. Figueroa, 548 F.3d 222, 226 (2d
Cir. 2008) (quoting Zervos v. Verizon N.Y., Inc., 252 F.3d 163, 169 (2d
Cir. 2001)).
19
A
In Vincent II, we held that the district court erred by awarding
compensatory damages for the enforcement of an unpronounced
term of post-release supervision without holding the plaintiff to the
burden of proving that the defendant state corrections official caused
the harm. See 63 F.4th at 151, 154-55. To meet that burden, it matters
“whether there was any impediment, legal or otherwise,” to the
corrections official “unilaterally releasing” the plaintiff. Id. at 154.
We explained that “[t]he burden is ‘normally on the plaintiff to
prove each element of a § 1983 claim, including those elements
relating to damages.’” Id. at 151 (quoting Miner v. City of Glens Falls,
999 F.2d 655, 660 (2d Cir. 1993)). First, “a plaintiff seeking
compensatory damages in a § 1983 suit must prove more than just a
deprivation of his rights; he must also establish that the ‘deprivation
caused him some actual injury.’” Id. (quoting McCann v. Coughlin,
698 F.2d 112, 126 (2d Cir. 1983)). Second, “when a defendant has
deprived the plaintiff of liberty, but the adverse action would have
been taken even in the absence of the wrongful conduct, the plaintiff
is entitled only to nominal damages.” Id. (alteration omitted) (quoting
Rentas v. Ruffin, 816 F.3d 214, 223 (2d Cir. 2016)). For that reason, the
district court must “reconstruct what would have ‘occurred had
proper procedure been observed.’” Id. (quoting Patterson v. City of
Utica, 370 F.3d 322, 338 (2d Cir. 2004)).
We said that the district court “improperly declined to consider
what steps were feasibly and legally available to [the state corrections
official], did not discuss [the plaintiff’s] burden of proving damages,
and did not determine whether [the plaintiff] had met that burden.”
Id. at 152. That “cursory treatment of damages causation does not
20
comport with our precedent and thus warrants remand and
reconsideration.” Id.
The same reasoning applies here. When it addressed Vincent II
in its decision denying the motion for a new trial, the district court
explained that the “jury weighed the evidence, drew inferences based
on the evidence, made credibility determinations, and reached
findings in reaching their verdict, including the award of damages.”
Santiago, 2023 WL 2974201, at *6. According to the district court, the
jury declined to credit the defendants’ testimony that they believed
they “had no authority to release individuals without a court order.”
Id. at *13 (internal quotation marks omitted). The district court
acknowledged, however, that the jury did not hear testimony
regarding the reasons for the defendants’ belief that “the DOCS and
DOP could not have excised the illegally imposed PRS” or the reasons
why the defendants “did not inform the District Attorneys’ offices or
[otherwise] rectify the situation.” Id. at *11.
The district court criticized the “trial testimony about Jenna’s
Law” that the defendants managed to present as “of marginal
relevance in explaining why they disregarded the mandates of Earley”
and as unpersuasive to the jury, which decided to “reject” the
“testimony regarding the justifications for why Defendants took as
long as they did to initiate compliance with Earley.” Id. at *19, *11. But
the absence of evidence that would explain the defendants’ conduct
resulted from the pretrial decision of the district court to exclude
relevant testimony about “what kind of constant litigation there was
about the meaning of Earley” and “what actions [the defendants] took
after the ruling in the Second Circuit.” J. App’x 534. The defendants
argued that “the jury should be able to hear what, in fact, was done
and why actions weren’t taken rather than leaving them with the
impression that the decision came across their desk and they looked
21
at it and threw it on the side.” Id. at 535. The defendants sought to
explain that “[i]t is not as if they weren’t taking action,” id., and that
“the law and the conduct of other State actors intervened to render
futile any efforts Defendants might have made in seeking
resentencing.” 12 The defendants would have explained, for example,
that they “reached out to the [Office of Court Administration]” and
“the D.A.s who were not going to do anything” because “the district
attorneys were arguing until they were blue in the face … that PRS is
mandatory.” J. App’x 536. 13
12 Defendants’ Memorandum of Law in Support of Their Motions in
Limine at 12, Santiago v. Cuomo, No. 12-CV-2137 (E.D.N.Y. July 29, 2022),
ECF No. 178.
13 Santiago suggests that some of this testimony would have been
inadmissible hearsay. See Appellee’s Br. 11, 29-30, 39. But the defendants’
testimony regarding arguments that district attorneys had made would
have been offered to prove that the district attorneys had made those
arguments, not that the arguments were substantively true. In other words,
statements of district attorneys would have been “introduced not for their
truth but only to show they were uttered.” United States v. Fernandez, 914
F.3d 1105, 1111 (7th Cir. 2019). Such evidence would have served “a
legitimate non-hearsay purpose aimed at providing the jury with the full
context” of the defendants’ actions by describing the impediments the
defendants faced, whether or not the impediments were justified. Id.; see
also United States v. Dupree, 706 F.3d 131, 136-38 (2d Cir. 2013) (explaining
that a court order may be introduced when “the significance of the Order
lies in the fact that it issued”). Moreover, “a statement offered to show its
effect on the listener is not hearsay.” Dupree, 706 F.3d at 136; see also United
States v. Johnson, 117 F.4th 28, 49 (2d Cir. 2024) (explaining that an email was
“admitted not for the truth of the matter asserted but to establish ‘a state of
mind,’ which ‘can be proved circumstantially by statements which are not
intended to assert the truth of the fact being proved’”) (quoting United States
v. Quinones, 511 F.3d 289, 312 (2d Cir. 2007)).
22
The exclusion of such evidence relieved Santiago of the burden
of proving causation and therefore the district court never
determined whether he “carried his burden of proving the extent to
which he is entitled to compensatory damages.” Vincent II, 63 F.4th at
155. Because the exclusion of evidence of impediments did “not
comport with our precedent,” it “warrants remand and
reconsideration.” Id. at 152.
B
Our decision in Vincent II involved compensatory damages, but
its logic applies with all the more force in a case such as this one
involving an award of punitive damages. “Punitive damages are
available in a § 1983 action ‘when the defendant’s conduct is shown
to be motivated by evil motive or intent, or when it involves reckless
or callous indifference to the federally protected rights of others.’” Lee
v. Edwards, 101 F.3d 805, 808 (2d Cir. 1996) (quoting Smith v. Wade, 461
U.S. 30, 56 (1983)). A procedural due process violation will not justify
punitive damages absent “evidence of the sort of egregious behavior
that would warrant such damages.” Kim v. Hurston, 182 F.3d 113, 121
(2d Cir. 1999); see also Earley, 451 F.3d at 76 n.1 (describing the
“procedural requirements in sentencing” as “based in the due process
guarantees of the United States Constitution”).
No direct evidence was presented at trial of malicious intent or
evil motive. The evidence at trial showed only that the defendants did
not promptly release Santiago after Earley or contact other state actors
who had the authority to seek his release. As the district court
recognized, “the jury decided” that the “unreasonable delay in
complying with Earley”—and that delay alone—“constituted callous
and reckless disregard of [Santiago’s] constitutional rights and caused
his injuries.” Santiago, 2023 WL 2974201, at *10.
23
We explained in Aponte that a plaintiff may be able to show
callous indifference based on the “failure to take prompt action to end
the custody of prisoners unconstitutionally detained for violating PRS
terms” despite being “aware of the holding and implications of
Earley.” 75 F.4th at 56. The inference would be possible when an
“unexcused delay” evinces a “deliberate refusal to comply with
Earley” that “shows ‘conscious wrongdoing’ and a ‘reckless or callous
indifference to federally protected rights,’ and hence can serve as a
basis for punitive damages.” Id. (alteration omitted) (quoting New
Windsor Volunteer Ambulance Corps, Inc. v. Meyers, 442 F.3d 101, 121
(2d Cir. 2006)).
But the defendants here sought to establish that the delay was
not “unexcused” and did not establish callous indifference because
the defendants faced “impediment[s], legal or otherwise,” to
“unilaterally releasing” Santiago or persuading the state actors with
authority to resolve the problem of an unpronounced term of post-
release supervision. Vincent II, 63 F.4th at 150, 154. Neither the district
court nor the jury made any determination about the “validity and
effect” of the purported impediments on either “the length of
[Santiago’s] unlawful incarceration” or the defendants’ state of mind
during the period of delay in 2007-08. Id. at 154. The district court
simply put the evidence of those impediments aside. But a delay in
complying with Earley when the corrections official has been
thwarted in seeking to address terms of post-release supervision or
believes he lacks the authority to order release would not establish
conscious wrongdoing or the reckless or callous indifference required
for an award of punitive damages. The district court abused its
discretion by excluding the evidence of impediments that would have
allowed the defendants to present that defense.
24
C
Santiago argues that the exclusion of the defendants’ evidence
of impediments was a harmless error. We disagree.
An evidentiary error may be considered harmless only “if we
can conclude with ‘fair assurance’ that the jury’s ‘judgment was not
substantially swayed by the error.’” United States v. Paulino, 445 F.3d
211, 219 (2d Cir. 2006) (quoting Kotteakos v. United States, 328 U.S. 750,
765 (1946)). In this case, “the burden rests upon [Santiago],” Vincent II,
63 F.4th at 154, to “establish[] that he suffered an injury as a result of
[the defendants’] failure to follow our directive in Earley that would
not have occurred otherwise,” Aponte, 75 F.4th at 57 (emphasis added)
(quoting Vincent II, 63 F.4th at 152). We cannot conclude that the jury
would have found that Santiago would have been released but for the
defendants’ failure to act to release him if it had heard evidence that
the defendants could not accomplish that result. Similarly, Santiago
was required to establish that the defendants acted with at least
“reckless or callous indifference.” Id. at 55. A reasonable jury might
conclude that an unexplained failure to release Santiago showed such
indifference based on the assumption that the defendants were aware
that they could release him. But we cannot conclude that the jury
would have made the same inference after hearing evidence of the
reasons that the defendants believed they could not.
The district court abused its discretion by excluding the
evidence of impediments and therefore erred by denying the motion
for a new trial.
II
We review the denial of qualified immunity de novo. See Vega v.
Semple, 963 F.3d 259, 272 (2d Cir. 2020). “[O]fficers are entitled to
qualified immunity under § 1983 unless (1) they violated a federal
25
statutory or constitutional right, and (2) the unlawfulness of their
conduct was ‘clearly established at the time.’” District of Columbia v.
Wesby, 583 U.S. 48, 62-63 (2018) (quoting Reichle v. Howards, 566 U.S.
658, 664 (2012)). The unlawfulness was not clearly established unless,
“at the time of the officer’s conduct, the law was sufficiently clear that
every reasonable official would understand that what he is doing is
unlawful.” Id. at 63 (internal quotation marks omitted).
With respect to the 2007-08 period, the defendants explain that
they “primarily raise the issue of qualified immunity here to preserve
it for further review,” acknowledging “earlier decisions” of this court
“denying qualified immunity in connection with post-Earley
enforcement of PRS terms not separately pronounced at sentencing.”
Appellants’ Br. 52.
The qualified immunity analysis “focuses on the specific factual
situation the officers confronted, and the defendants will be entitled
to qualified immunity unless existing precedent squarely governs the
specific facts at issue.” McKinney v. City of Middletown, 49 F.4th 730,
739 (2d Cir. 2022) (internal quotation marks and alterations omitted).
The defendants argue that the circumstances of this case are
distinguishable from those in Earley and, as a result, Earley does not
preclude the application of qualified immunity. In Earley, the plaintiff
“was not informed of this mandatory provision [of post-release
supervision] during plea negotiations, the plea allocution, or at the
time his … sentence was imposed.” 451 F.3d at 73; see Vincent v. Yelich
(Vincent I), 718 F.3d 157, 162 (2d Cir. 2013) (“Neither prior to the entry
of his guilty plea nor at his sentencing was [Earley] informed that he
26
was subject to a term of PRS, and his commitment order did not refer
to PRS conditions.”). 14
In this case, however, Santiago was informed during his plea
hearing that he would be subject to a mandatory term of five years of
post-release supervision, and he agreed to that sentence. See J. App’x
353. The record does not suggest that the sentencing court altered the
plea bargain that Santiago accepted.
In addition, the defendants identify evidence explaining why
they believed that they lacked the authority to release Santiago or to
refer him for resentencing. We have previously denied qualified
immunity on the understanding that “immediately after Earley I
and II were decided in 2006 [the corrections officials] could have
undertaken the remedial measures that they later took when
prompted by Smith, Garner and Sparber in the spring of 2008.”
Betances, 837 F.3d at 170. Only later did we “clarify” that a
resentencing was not “a viable avenue” for all defendants and that
the “remaining option” of excising sentences of post-release
supervision might have required “court approval.” Vincent II, 63 F.4th
at 154. The defendants suggest that the new evidence—of “any
impediment, legal or otherwise, to [the DOCS] simply and
unilaterally releasing” an inmate—ought to affect the determination
14 The Vincent I plaintiffs similarly “alleged that each of the plaintiffs
pleaded guilty to a felony under New York law; that none of the plaintiffs
was informed by the sentencing judge that he was subject to a PRS term;
that none of the plaintiffs’ commitment orders mentioned a PRS term; and
that each plaintiff was subjected to a PRS term administratively imposed by
DOCS.” Vincent I, 718 F.3d at 175. Those circumstances led us to conclude
that state corrections officials were not “entitle[d] to qualified immunity.”
Id.
27
of what a reasonable official would have been expected to do under
the circumstances. Id.
As the defendants acknowledge, however, that is not how we
have previously addressed the question of qualified immunity in this
context. We have understood Earley to stand for the proposition that
“[o]nly the judgment of a court, as expressed through the sentence
imposed by a judge, has the power to constrain a person’s liberty.”
Earley, 451 F.3d at 75. Accordingly, we have identified the “precise
conduct” that Earley prohibits as the “administrative imposition of
PRS on a prisoner who has not had that condition imposed on him by
the sentencing court.” Vincent I, 718 F.3d at 168. That prohibition does
not appear to turn on whether the defendant was made aware of the
PRS term during a plea hearing that preceded the sentencing.
We have also categorially held that the state corrections
officials “understood that Earley I required them to change their
practices” but “did not take objectively reasonable steps to comply.”
Betances, 837 F.3d at 172. In Betances, we “determined” that the steps
the defendants eventually took to comply with Earley “were not an
objectively reasonable justification for the defendants’ delay in
seeking resentencing of prisoners with administratively imposed PRS
terms.” Hassell v. Fischer, 879 F.3d 41, 51 (2d Cir. 2018).
Given these precedents, we agree with the district court that the
defendants are not entitled to qualified immunity for conduct during
the 2007-08 period. The defendants offer a reasonable argument that
(1) the evidence of impediments may ultimately show that any
further actions they might have taken would have been futile given
the conduct of state actors with the relevant authority, so (2) “a
reasonable officer” in their position could not have been expected to
act differently. Plumhoff v. Rickard, 572 U.S. 765, 775 (2014) (quoting
28
Graham v. Connor, 490 U.S. 386, 396 (1989)). But while we have held
that such evidence is relevant to the issues of causation and punitive
damages, we have also held that “[t]he efforts made, or not made, by
other parties are beside the point for the purposes of determining
qualified immunity.” Betances, 837 F.3d at 174. That holding controls
the decision here.
III
Santiago argues that the decision of the district court with
respect to his claims for the incarceration from September to
December 2010 conflicts with our statement in Hassell v. Fischer that
“the defendants are foreclosed by Betances II from arguing that their
belated, albeit reasonable, steps to comply with Earley I excuse the
initial unreasonable delay.” 879 F.3d at 51. He contends that the
district court erred in ruling on summary judgment that qualified
immunity bars relief for the time Santiago spent in custody in 2010. In
this appeal, the defendants “do not contest this asserted error.”
Appellants’ Reply Br. 29. Instead, the defendants argue that “an
impediments analysis is nonetheless warranted for this time period.”
Id.
We agree with the parties that our precedents foreclose the
conclusion that qualified immunity prevents Santiago from obtaining
relief for the months he spent in custody in 2010. As a result, we
vacate the judgment insofar as the district court granted summary
judgment on those claims based on qualified immunity. But for the
reasons explained above, the evidence of impediments is relevant to
determining whether the defendants caused Santiago’s detention
during that period. On summary judgment, the district court
determined that in 2008 the defendants “began to take what the
Second Circuit termed ‘reasonable steps toward bringing DOCS and
29
DOP into compliance with Earley I’” but that the defendants could not
have acted before September 2010 with respect to Santiago, who “was
not within New York’s jurisdiction until September 14, 2010.”
Santiago, 2017 WL 11929991, at *10 (quoting Betances, 837 F.3d at 172).
While the defendants cannot obtain qualified immunity, these
arguments may be relevant to any renewed motion for summary
judgment with respect to liability for 2010. We remand to allow the
district court to consider, on any such motion, the effect that evidence
of impediments may have on the defendants’ defense to liability for
that period.
CONCLUSION
We reverse the judgment of the district court insofar as it
denied the motion for a new trial related to the 2007-08 period. We
vacate the judgment insofar as the district court dismissed the claims
related to 2010 on the ground of qualified immunity. We remand for
further proceedings consistent with this opinion.
30