Villalobos-Santana v. PR Police Department

U.S. Court of Appeals for the First Circuit Filed 2026-04-02 No. 24-1776
Jimmy Villalobos-Santana and Jimmy Colón-Rodríguez sued the Puerto Rico Police Department in July 2021 under 42 U.S.C. § 2000 et seq., alleging retaliation after they complained to the EEOC about age discrimination. They litigated in federal district court for nearly three years — through discovery, summary judgment (which they survived in part), and into pretrial preparation. Then in May 2024, days before trial, the Department filed a 'Notice of Injunction' asserting that Puerto Rico's PROMESA Plan of Adjustment had discharged the claims. The district court granted a permanent stay and injunction on the ground that the claims had arisen before the Effective Date. The First Circuit affirmed, but on a different rationale: under Reading v. Brown and its progeny (including Ellis and Charlesbank Laundry), claims arising from the debtor's continued operations during reorganization — including employment discrimination and retaliation claims — qualify as 'administrative expenses' under 11 U.S.C. § 503(b), which PROMESA incorporates. Because the plaintiffs did not timely file proof of their claims before the administrative-expense bar date, their claims were discharged. The panel rejected the plaintiffs' judicial-estoppel argument, finding the Department had consistently preserved PROMESA defenses in its filings. Judge Thompson concurred dubitante, agreeing the result is likely correct but expressing serious concern about the late invocation of discharge, the loss of Seventh Amendment jury-trial rights, and the implications for civil-rights plaintiffs in post-PROMESA Puerto Rico. She noted plaintiffs may still petition the Title III court to accept a late administrative-expense claim 'for cause' under § 503(a).

Summary

Jimmy Villalobos-Santana and Jimmy Colón-Rodríguez sued the Puerto Rico Police Department in July 2021 under 42 U.S.C. § 2000 et seq., alleging retaliation after they complained to the EEOC about age discrimination. They litigated in federal district court for nearly three years — through discovery, summary judgment (which they survived in part), and into pretrial preparation. Then in May 2024, days before trial, the Department filed a 'Notice of Injunction' asserting that Puerto Rico's PROMESA Plan of Adjustment had discharged the claims. The district court granted a permanent stay and injunction on the ground that the claims had arisen before the Effective Date. The First Circuit affirmed, but on a different rationale: under Reading v. Brown and its progeny (including Ellis and Charlesbank Laundry), claims arising from the debtor's continued operations during reorganization — including employment discrimination and retaliation claims — qualify as 'administrative expenses' under 11 U.S.C. § 503(b), which PROMESA incorporates. Because the plaintiffs did not timely file proof of their claims before the administrative-expense bar date, their claims were discharged. The panel rejected the plaintiffs' judicial-estoppel argument, finding the Department had consistently preserved PROMESA defenses in its filings. Judge Thompson concurred dubitante, agreeing the result is likely correct but expressing serious concern about the late invocation of discharge, the loss of Seventh Amendment jury-trial rights, and the implications for civil-rights plaintiffs in post-PROMESA Puerto Rico. She noted plaintiffs may still petition the Title III court to accept a late administrative-expense claim 'for cause' under § 503(a).

Structured facts

Parties
Petitioner/Appellant: Jimmy Villalobos-Santana and Jimmy Colón-Rodríguez (plaintiffs-appellants)
Respondent/Appellee: Puerto Rico Police Department (defendant-appellee)
Jurisdiction
federal — First Circuit on appeal from the District of Puerto Rico
Statutes cited
42 U.S.C. § 2000 et seq. (Title VII), 48 U.S.C. §§ 2101-2241 (PROMESA), 48 U.S.C. § 2161(a) (incorporating Bankruptcy Code into PROMESA), 11 U.S.C. §§ 503(a), 503(b), 507(a)(2), 524(a)(2), 944, U.S. Const. amend. VII (jury trial)
Issue
Whether retaliation claims against a Puerto Rico government instrumentality that arose mostly post-petition but before the PROMESA Plan's Effective Date qualify as administrative-expense claims under § 503(b), and thus are discharged if not timely filed.
Holding
Yes. Under Reading's expansive definition — as extended to employment-based claims by Ellis (3d Cir.) and Sanchez (8th Cir.), and embraced by First Circuit precedent (Charlesbank Laundry, Munce's) — retaliation claims arising from the debtor's continued operations are administrative expenses. Because the plaintiffs did not timely file, the claims are discharged. Judicial estoppel does not apply because the Department preserved its PROMESA defenses from its first answer.
Outcome
affirmed on alternative grounds
Vote
Barron (majority, joined by Aframe); Thompson concurring dubitante
Majority author
Chief Judge Barron

Key facts

Reasoning

Administrative expenses under § 503(b) are 'actual, necessary costs and expenses of preserving the estate' — a term Reading interpreted broadly to include tort and other claims arising from the debtor's ongoing operations. Circuits including the Third (Ellis) and Eighth (Sanchez) have applied that broad reading to employment-discrimination claims, and the First Circuit sees no reason PROMESA should be read more narrowly than the Bankruptcy Code it incorporates. The Department's litigation conduct did not support judicial estoppel because it repeatedly recited that it appeared 'without waiving any right, objection or defense arising from the Title III of PROMESA.' The panel did not decide whether plaintiffs could obtain relief by filing late 'for cause' in the Title III court.

Implications

The decision is the First Circuit's most consequential statement on how PROMESA interacts with ongoing civil-rights and employment litigation. Four implications. First, post-petition but pre-Effective-Date civil-rights claims against Commonwealth instrumentalities — Title VII, § 1983, age-discrimination, disability-discrimination — are likely administrative expenses, not ordinary claims. Claimants must file with the Title III court by the administrative-expense bar date or risk discharge. Second, the broad Reading-based reading of administrative expenses may raise collateral questions that Judge Thompson flagged in her concurrence: what happens to the Seventh Amendment jury-trial right for an administrative-expense claim that must be adjudicated in the bankruptcy court? See In re Highcrest Mgmt., where relief-from-stay allowed jury trial. Third, Judge Thompson's concurrence is a roadmap for late filings: § 503(a)'s 'for cause' exception remains available and should be invoked aggressively, particularly where the defendant's litigation conduct created the timing problem. Fourth, defense counsel representing Puerto Rico instrumentalities can now confidently rely on the Plan's discharge effect even where they raised PROMESA only generically at the outset — but doing so late in litigation carries reputational risk and the possibility of Title III court sympathy for late claimants on remand.

Related cases

Practical guide

For Puerto Rico civil-rights plaintiffs' counsel: (1) in any suit against a Commonwealth instrumentality, treat PROMESA timelines as mission-critical — file parallel administrative-expense claims in the Title III court immediately; (2) if a discharge defense is raised late, pivot to § 503(a) 'for cause' late-filing in the Title III court, citing Villalobos-Santana Footnotes 2 and 4 and Judge Thompson's concurrence; (3) preserve Seventh Amendment jury-trial arguments for potential relief-from-stay motions. For Department counsel and Puerto Rico defense attorneys: raise PROMESA discharge early and clearly — not just via boilerplate reservations — to avoid the reputational and potential Title III 'for cause' exposure that late invocation creates. For federal district judges in Puerto Rico: at early case-management conferences, raise PROMESA implications and require parties to address administrative-expense filing status on the record. For the Title III court: Villalobos-Santana opens the door to a wave of 'for cause' late filings from previously active civil-rights cases; a clear standard for evaluating them would be helpful. For labor-and-employment practitioners outside Puerto Rico: Ellis and Villalobos-Santana together indicate that state-agency bankruptcies (e.g., Detroit-style municipal reorganizations) may increasingly sweep employment claims into administrative-expense discharge.

FAQ

Does this ruling mean plaintiffs lose their civil-rights claims automatically?

Not necessarily. The ruling only affects forum and timing: plaintiffs must go through the Title III bankruptcy court rather than the district court. Judge Thompson's concurrence emphasizes that § 503(a) permits 'for cause' late filings, which the Title III court may accept — especially where the defendant's late invocation contributed to the missed deadline.

Why didn't judicial estoppel prevent the Police Department from waiting to raise the discharge defense?

The majority held the Department consistently preserved PROMESA defenses in its filings by reciting it appeared 'without waiving any right' under PROMESA. Judge Thompson's concurrence disagreed on the judicial-estoppel merits, but agreed the result is likely compelled by 11 U.S.C. § 524(a)(2), which makes discharge effective regardless of waiver.

What about the Seventh Amendment right to a jury trial?

Judge Thompson flagged this concern explicitly. Administrative-expense claims are typically resolved by the bankruptcy court without juries, raising serious constitutional questions. In at least one prior case (Highcrest Management), courts have lifted the stay to allow jury trials — plaintiffs in similar cases should consider seeking such relief.

This is not legal advice. This is analysis of publicly published court opinions. Source: CourtListener. Consult a licensed attorney for advice about your specific situation.