Full Opinion

United States Court of Appeals For the First Circuit No. 21-1232 JULIO ORTIZ-RESTO; CARLOS GUERRA-CRUZ; JOSE FUENTES-RODRIGUEZ; CARMEN PABON-COTTEA; REY ANDINO-PLAZA; RAMON RIVERA-LOPEZ; WILFREDO DIAZ-JIMENEZ; BENYAMIL MORALES-COLON; KELVY SANTIAGO-RODRIGUEZ; ELIZABETH COLON-RODRIGUEZ; ADOLF MORALES-RUIZ; XIOMARA RIVERA-CABRERA; CARLOS CIRINO-ROBLES; HECTOR FIGUEROA-VAZQUEZ; LYNNETTE LOPEZ-OJEDA; PIERRE VEGA-ALAMEDA; EMANUEL CORREA-COLON; HECTOR SANTIAGO-HERNANDEZ; FRANCISCO REYES-NEGRON; HORIDEL PONS-ANAYA; GISELLE OCASIO-MORALES; GAMALIER CARDONA-SANCHEZ; JENNIFER HERNANDEZ-ADORNO; JEAN CARLOS COLON-RIVERA; LUIS OJEDA-RODRIGUEZ; JONATHAN TORRES-OVALLES; NANCY LOPEZ-MORALES; ILEANA PEREZ-MENDEZ; DAVID SILVA-IRIZARRY; LOURDES RUIZ-ANDRINO; JESSICA RIVERA FERRER; NOEL BERRIOS-RODRIGUEZ; JOSE RIVERA-PARILLA; JOSE MELENDEZ-LEBRON; LARRY RONDON-VAZQUEZ; CARLOS KUIDLAND-DIAZ; ANA RODRIGUEZ-SANTANA; RAMPHIS BAEZ-CALDERON; CHRISTOPHER DECENE-GARCIA; FELIX RIVERA-ROLON; DENISE RIVERA-COLON; ELI DIAZ-JIMENEZ; JULIA RODRIGUEZ-LOPEZ; LUIS ANTONIO CHICO RIOS; MIGUEL ALFONSO CHICO RIOS; MANUEL CHICO RIOS; ROBERTO CHICO RIOS, Plaintiffs, Appellees, v. THOMAS RIVERA-SCHATZ, President of the Senate of the Commonwealth of Puerto Rico; ROBERTO MALDONADO-VÉLEZ, Administrative Secretary of the Senate of the Commonwealth of Puerto Rico; GABRIEL HERNÁNDEZ-RODRÍGUEZ, Chief of Staff of the President of the Senate of the Commonwealth of Puerto Rico, Defendants, Appellants. APPEAL FROM THE UNITED STATES DISTRICT COURT FOR THE DISTRICT OF PUERTO RICO [Hon. William G. Young,* U.S. District Judge] Before Barron, Chief Judge Breyer,** Associate Justice and Thompson, Circuit Judge Eduardo A. Vera Ramírez argued, with whom Luis A. Rodríguez Muñoz and Landrón Vera, LLC were on brief for appellee. Omar Andino-Figueroa, Solicitor General of Puerto Rico, with whom Frank A. Rosado Méndez, Deputy Solicitor General, and Mariola Abreu-Acevedo, Assistant Solicitor General were on brief, for appellant. November 3, 2026 * Of the District of Massachusetts, sitting by designation. ** Hon. Stephen G. Breyer, Associate Justice (Ret.) of the Supreme Court of the United States, sitting by designation. BARRON, Chief Judge. This interlocutory appeal comes to us in connection with a suit by three former employees of the Senate of the Commonwealth of Puerto Rico. The defendants are officials in the Senate of the Commonwealth of Puerto Rico. They moved for summary judgment based on qualified immunity as to certain claims that three of those former employees brought. In those claims, the three former employees seek damages from the defendants in their personal capacities under 42 U.S.C. § 1983. They do so on the ground that the defendants violated their rights under the First Amendment to the U.S. Constitution by firing them from their Senate positions based on their partisan political affiliation. The District Court denied the motion. The defendants now appeal from that ruling insofar as it rejected their claim of qualified immunity. We affirm. I. The three former employees who bring the claims before us in this interlocutory appeal were among dozens of former Senate employees who filed the underlying suit in the U.S. District Court for the District of Puerto Rico in December 2017. The named defendants are Thomas Rivera-Schatz, the President of the Senate; Roberto Maldonado-Vélez, the Administrative Secretary of the Senate; and Gabriel Hernández-Rodríguez, the Chief of Staff of the President of the Senate. - 3 - The full set of plaintiffs brought several different equitable and monetary damages claims in the initial suit, including due process and equal protection claims, as well as claims under Puerto Rico law. Many of those claims were dismissed pursuant to Federal Rule of Civil Procedure 12(b)(6) for failure to state a claim upon which relief may be granted. One of the claims was dismissed at the summary judgment stage. Other surviving claims are not at issue in this appeal. The only claims at issue in this appeal were brought by the following three former Senate employees: Elizabeth Colón-Rodriguez ("Colón"), Pierre Vega-Alameda ("Vega"), and Horidel Pons-Anaya ("Pons"). The operative complaint alleges that Colón held the position of Protocol Officer in the Office of Protocol and Activities for the Senate and that Vega and Pons held the position of Liaison Technician in the Office of Governmental Affairs for the Senate. This appeal concerns only their First Amendment-based, personal-capacity damages claims against the defendants. The defendants moved for summary judgment as to those specific claims. They did so in part by asserting that they were entitled to qualified immunity. The District Court denied the motion, and the defendants timely sought interlocutory review of that ruling insofar as it denied them summary judgment based on qualified immunity. - 4 - II. The three former employees contend that we lack appellate jurisdiction to review the District Court's denial of the defendants' motion for summary judgment, even insofar as the defendants are challenging only the District Court's qualified immunity ruling. The three former employees rely on Johnson v. Jones, 515 U.S. 304 (1995), in so arguing. Johnson establishes that "a defendant, entitled to invoke a qualified immunity defense, may not appeal a district court's summary judgment order insofar as that order determines whether or not the pretrial record sets forth a 'genuine' issue of fact for trial." Id. at 319-20. In such circumstances, Johnson explains, the appellate court lacks appellate jurisdiction to hear an interlocutory appeal because "the issue . . . at stake -- the existence, or nonexistence, of a triable issue of fact -- is the kind of issue that trial judges, not appellate judges, confront almost daily. Institutionally speaking, appellate judges enjoy no comparative expertise in such matters." Id. at 316. Johnson contrasted such circumstances, however, with those in which "purely legal matters are at issue," as Johnson allowed the defendant invoking the qualified immunity defense to bring an appeal of the denial of summary judgment based on qualified immunity on an interlocutory basis. Id. The Court explained in Johnson that "'[i]mmunity appeals . . . interfere - 5 - less with the final judgment rule if they [are] limited to cases presenting neat abstract issues of law.'" Id. at 317 (alteration in original)(quoting 15A C. Wright, A. Miller, and E. Cooper, Federal Practice and Procedure § 3914.10 at 664 (1992)). In the interlocutory appeal at hand, the three former employees argue that we lack appellate jurisdiction under Johnson because of what they assert is the fact-dependent nature of the defendants' grounds for challenging the District Court's denial of their motion for summary judgment based on qualified immunity. The defendants disagree with that characterization of their grounds for appeal. Wholly apart from this threshold dispute over our appellate jurisdiction under Johnson, however, the defendants contend that there is no reason for us to reach the merits of their challenge to the District Court's ruling as to qualified immunity. They contend that, even if we were to conclude that we have appellate jurisdiction under Johnson and so would not for that reason be barred from addressing the challenge on the merits, we still would have to remand the plaintiffs' claims at issue on appeal to the District Court with orders to "dismiss or permanently stay the action." The reason, according to the defendants, is that, while their interlocutory appeal was pending, the claims that are at issue in it were discharged in the bankruptcy proceedings involving - 6 - the Commonwealth of Puerto Rico that are being conducted pursuant to the Puerto Rico Oversight, Management, and Economic Stability Act ("PROMESA"). 48 U.S.C. § 2101 et seq. As a result, the defendants contend that, whether or not they are entitled to qualified immunity as to the claims that are at issue in their interlocutory appeal, it is no longer possible for the plaintiffs to obtain the relief that the plaintiffs seek on those claims. Accordingly, the defendants contend, we cannot address the merits of the defendants' challenge on appeal to the denial of their motion for summary judgment based on qualified immunity, as the claims for which the defendants have sought dismissal on summary judgment must be either dismissed or permanently stayed because they have been discharged. The defendants' contention rests on an order that was issued in 2022 by the federal district court that PROMESA vested with jurisdiction over the bankruptcy proceedings involving the Commonwealth. In re Fin. Oversight & Mgmt. Bd. of P.R., 636 B.R. 1 (D.P.R. 2022). That order not only confirmed the Plan of Adjustment for the Commonwealth that had been adopted by the PROMESA-created Financial Oversight and Management Board but also discharged and enjoined the pursuit of certain claims against the Commonwealth. Id. at 38. The defendants contend that the claims before us in this interlocutory appeal were among the claims subject to that order. - 7 - We may easily dispose of the defendants' PROMESA-related contention. And that is so even assuming that it is properly before us in this interlocutory appeal. See Posada v. Cultural Care, Inc., 66 F.4th 348, 356 n.6 (1st Cir. 2023) (quoting Cowels v. Fed. Bureau of Investigation, 936 F.3d 62, 67 (1st Cir. 2019)) ("Where a question of statutory jurisdiction is complex, but the merits of the appeal are easily resolved against the party invoking [] jurisdiction, we can assume jurisdiction for purposes of deciding the appeal." (internal quotation marks omitted)(alteration in original)); cf. Asociación De Subscripción Conjunta Del Seguro De Responsabilidad Obligatorio v. Flores Galarza, 484 F.3d 1, 20 n.22 (1st Cir. 2007) ("[A]ppellate jurisdiction extends to issues of standing on interlocutory appeal of a denial of immunity."); Arizonans for Off. Eng. v. Arizona, 520 U.S. 43, 68 n.22 (1997) ("Mootness has been described as the doctrine of standing set in a time frame[.]" (internal quotation marks omitted)). We recently held in In re Fin. Oversight & Mgmt. Bd. of P.R., 178 F.4th 747, 751 (1st Cir. 2026), that the order on which the defendants' contention rests "does not apply to personal-capacity claims and that such claims are therefore not subject to any injunction impeding their prosecution." Indeed, we explained that "discharging personal-capacity claims would constitute a non-consensual third-party release, thereby running - 8 - afoul of the Plan's plain language and diverging from the Supreme Court's reasoning in [Harrington v. Purdue Pharma L.P., 603 U.S. 204 (2024)]"1 In re Fin. Oversight & Mgmt. Bd. of P.R., 178 F.4th at 759. Thus, the claims at issue in this interlocutory appeal clearly were not discharged. As a result, we must circle back to the parties' dispute about our appellate jurisdiction under Johnson to address the merits of the defendants' challenges to the District Court's denial of their motion for summary judgment based on qualified immunity. We will address the merits of those challenges only insofar as we have appellate jurisdiction to do so. III. We first will describe both the relevant qualified immunity standard and the District Court's ruling denying the defendants' motion for summary judgment based on qualified immunity. We then will address each of the defendants' challenges to that ruling. In each instance, we will first analyze the plaintiffs' threshold contention regarding our appellate 1This decision emphasized that "in the analogous context of corporate bankruptcy, releasing claims against third parties involves exercising a 'radically different power' than releasing claims against the debtor -- a power with which bankruptcy courts are 'not endow[ed].'" In re Fin. Oversight & Mgmt. Bd. of P.R., 178 F.4th at 756 (alterations in original). - 9 - jurisdiction under Johnson to address the merits of the challenge before then resolving the merits of the challenge insofar as we have jurisdiction to do so. A. "In deference to the sensitive discretionary judgments that government officials are obliged to make, qualified immunity safeguards even unconstitutional conduct if a reasonable officer at the time and under the circumstances surrounding the action could have viewed it as lawful." Jordan v. Carter, 428 F.3d 67, 71 (1st Cir. 2005). "[W]e follow a two-prong analysis for determining whether defendants are entitled to qualified immunity, asking '(1) whether the facts alleged or shown by the plaintiff make out a violation of a constitutional right; and (2) if so, whether the right was 'clearly established' at the time of the defendant's alleged violation.'" Díaz-Bigio v. Santini, 652 F.3d 45, 50 (1st Cir. 2011)(citation omitted). The second prong, we have said, "has two parts: (a) whether the legal contours of the right in question were sufficiently clear that a reasonable official would have understood that what he was doing violated that right, and (b) whether the particular factual violation in question would have been clear to a reasonable official." Díaz-Bigio, 652 F.3d at 50. In the political discrimination context, we have articulated that inquiry as follows: whether 1) "defendants were - 10 - entitled to consider [the plaintiffs'] political affiliation as a job qualification" and 2) "even if they were not, whether a reasonable officer at the time would have understood patronage dismissal to be barred." López-Quiñones v. P.R. Nat'l Guard, 526 F.3d 23, 25 (1st Cir. 2008). The three former employees allege in the claims at issue in this interlocutory appeal that, under the First Amendment, the defendants were not entitled to consider the three former employees' political affiliation as a job qualification. The three former employees acknowledge, though, that the First Amendment barred their political affiliation from serving as a job qualification only if the positions that they held in the Senate of the Commonwealth did not "involve government decisionmaking on issues where there is room for political disagreement on goals or their implementation[.]" Jimenez Fuentes v. Torres Gaztambide, 807 F.2d 236, 241–42 (1st Cir. 1986) (en banc). If their positions did involve such government decisionmaking, and if their positions "resemble[] a policymaker, a privy to confidential information, a communicator, or some other office holder whose function is such that party affiliation is an equally appropriate requirement," then the three former employees were not protected under the First Amendment from dismissal based on their partisan political affiliation. See id. at 242. - 11 - In denying the defendants' motion for summary judgment based on qualified immunity, the District Court addressed whether a reasonable officer at the time would have understood the three former employees' dismissal based on their partisan political affiliation to be barred.2 To that end, the District Court held that the defendants were not entitled to a summary judgment grant of qualified immunity on reasonableness grounds for two independent reasons. First, the District Court denied the motion on the ground that "[w]here there are questions of fact as to whether the positions were protected from patronage dismissal, the Court also rules that genuine issues of material fact preclude a determination of objective reasonableness for qualified immunity to attach on this record." The District Court determined that those "genuine issues of material fact" were rooted in a lack of clarity about "exactly what duties these plaintiffs performed." The District Court considered two forms of evidence in making this determination: official job descriptions and testimony from the plaintiffs about the duties they performed. 2 It is not a problem to rest the denial solely on the second question, since we have said that "[a]nalytically, the second question may often be answered without resolving the first." López-Quiñones, 526 F.3d at 25. - 12 - Second, the District Court determined that, "in the alternative," the defendants were not entitled to summary judgment based on qualified immunity because there were genuine issues of material fact as to whether the defendants themselves had considered the nature of the plaintiffs' job duties before taking actions to have them removed from their positions in the Senate. The District Court explained that the question of whether the defendants considered the nature of the plaintiffs' job duties mattered because “a reasonable public official in light of the First Circuit’s developed case law must at least inquire as to the nature of the duties of the position based upon the history of political discrimination cases in Puerto Rico.” Accordingly, the District Court "question[ed] whether qualified immunity should inure to the benefit of defendants in political discrimination cases where there is no evidence that the officials’ actions included examining any of the plaintiffs’ duties at all.” B. We start with the defendants' challenge to the District Court's second ground for denying their summary judgment motion based on qualified immunity, in which the District Court determined that there were genuine issues of material fact about whether the defendants themselves had considered the nature of the plaintiffs' job duties. The defendants argue that the District Court committed legal error by relying on the existence of those issues, because - 13 - the District Court thereby impermissibly "import[ed] a subjective diligence standard into the qualified immunity framework." This challenge does not take issue with any of the District Court's factual premises. It takes issue only with a purely legal judgment that the District Court assertedly wrongly made. Because, under Johnson, we have appellate jurisdiction to assess this "purely legal" issue, see 515 U.S. at 313-16, there is no jurisdictional bar to our addressing this challenge to the District Court's qualified immunity ruling. As to the merits of the defendants' contention that the District Court erred as a matter of law in relying on this ground for denying their motion for summary judgment based on qualified immunity, the District Court relied on the reasoning set forth in a dissent to one of our prior precedents, López-Quiñones, 526 F.3d at 29-30 (Torruella, J., concurring in part, dissenting in part).3 We explained in López-Quiñones, however, that "[l]argely for prudential reasons, the test" for the qualified immunity inquiry, "is not subjective but asks what a reasonable official would have 3Judge Torruella asserted that it is "inconceivable in this day and age that a reasonable public official would by-pass an inquest into whether a position in a government agency requires political affiliation before taking the drastic action of firing an employee based on party affiliation. Considering the state of the law, one who fails to do so can hardly be classified as a reasonable public official." López-Quiñones, 526 F.3d at 29 (Torruella, J., concurring in part, dissenting in part). - 14 - thought." 526 F.3d at 27. Consistent with that objective inquiry, the majority in López-Quiñones assessed for itself the duties and responsibilities of the fired employees in the case and did not assess how the defendants themselves came to their understanding of the fired employees' job duties. Id. at 27-28. We therefore read López-Quiñones to have rejected Judge Torruella's contention in dissent that a reasonable official must "inquest into whether a position in a government agency requires political affiliation before taking the drastic action of firing an employee based on party affiliation," in order to be protected by qualified immunity. 526 F.3d at 29 (Torruella, J., concurring in part, dissenting in part). As a result, we agree with the defendants that the existence of genuine issues of material fact about whether the defendants themselves considered the nature of the plaintiffs' job duties has no bearing on whether the defendants are entitled to qualified immunity. It follows that the District Court erred, as a matter of law, in denying the motion for summary judgment on that particular ground. C. Nonetheless, as we have noted, the District Court also denied the defendants' motion for summary judgment based on qualified immunity on a distinct ground. In doing so, the District Court denied the motion because it determined that "genuine issues - 15 - of material fact preclude a determination of objective reasonableness for qualified immunity to attach on this record." We thus need to address the defendants' challenge to that basis for the District Court's ruling denying their motion for summary judgment based on qualified immunity. In pressing this challenge, the defendants contend that: [E]ven if this Court does not address whether Colón-Rodríguez, Vega-Alameda, and Pons-Anaya’s positions were protected positions, Defendants-Appellants are still entitled to qualified immunity. That is because . . . an objectively reasonable official in Defendants-Appellants’ position, acting at the time of Colón-Rodríguez’ termination, could conclude that the position of Protocol Officer in the [Office of Protocol and Activities] was not constitutionally protected. The same goes for the Liaison Technician [i]n the [Office of Governmental Affairs] position formerly held by Vega-Alameda and Pons-Anaya." (footnote omitted). Insofar as the defendants, in pressing this challenge, mean to be taking issue with the factual premises on which the District Court relied in denying them summary judgment, we are barred from considering the challenge's merits under Johnson. See 515 U.S. at 307 (holding that since "[t]he order in question resolved a fact-related dispute about the pretrial record . . . the defendants cannot immediately appeal this kind of fact-related district court determination" (emphasis in original)). But, - 16 - ultimately, the defendants contend that, "even accepting [the plaintiffs'] version of the facts, [they] are entitled to qualified immunity on the ground that a reasonable official in their position could have believed that the First Amendment permitted the terminations." And we have appellate jurisdiction to address this ground for challenge under Johnson, as it raises a purely legal question -- namely, whether, as a matter of law, the job positions at issue were such that a reasonable official could have understood them to have been unprotected. Even still, an appellant must "develop the argument that, even drawing all the inferences as the district court concluded a jury permissibly could, they are entitled to judgment as a matter of law." Cady v. Walsh, 753 F.3d 348, 359-60 (1st Cir. 2014) (emphasis added); see also McKenney v. Mangino, 873 F.3d 75, 81 (1st Cir. 2017) ("In other words, an appellant must explain why he is entitled to qualified immunity even if one assumes that the district court properly analyzed the facts."). The defendants have not done so here. To that point, the defendants assert as to the position of one of the three former Senate employees in question that: [E]ven assuming that on the spectrum Colón-Rodríguez’s position was closer to a non-policymaker and is, at least on the present record, protected under [Elrod v. Burns, 427 U.S. 347 (1976)] -- an objectively reasonable official in Defendants-Appellants’ position, acting at the time of - 17 - Colón-Rodríguez’ termination, could conclude that the position of Protocol Officer in the [Office of Protocol and Activities] was not constitutionally protected. But this conclusory assertion fails to engage with the District Court's reasoning, which, as noted above, rested in part on testimony about the plaintiffs' job duties and not merely formal job descriptions. It thus fails to explain why the position was one that, as a matter of law, a reasonable official could deem it to be unprotected when the evidence is viewed in the light most favorable to the plaintiffs. A similar problem plagues the defendants' further contention that "when reasonable officials could disagree about whether a position is exempt from political patronage dismissal, qualified immunity must apply." Here, too, the assertion sets forth a conclusion rather than an argument. It is possible that, in making those seemingly conclusory assertions, the defendants mean to be arguing that, as a matter of law, the formal job descriptions of the three former employees are such that, in and of themselves, they compel the conclusion that a reasonable official could deem the positions unprotected. In other words, the defendants may mean to be arguing that, whatever the testimony on which the District Court relied in denying summary judgment might show, that testimony is simply - 18 - irrelevant for purposes of the qualified immunity inquiry because of the nature of the plaintiffs' formal job descriptions. The defendants do gesture at such an argument when they assert in a footnote the following from Colón's official job description -- that she was responsible for coordinating, developing, and participating in the official activities of the Puerto Rico Senate, and that she was "exercis[ing] initiative and personal judgment in the performance of his or her duties." These duties, the defendants suggest, "might have led a reasonable official involved in the termination decision to believe she was subject to patronage dismissal." In that same vein, the defendants also contend that "[t]he formal job descriptions . . . set forth broad duties implicating discretion, initiative, and public-facing responsibilities that support a reasonable inference that political affiliation could be a legitimate employment criterion." And they emphasize at one point (and again in a footnote) that we have held that, with respect to assessing job duties, “what counts are the attributes inherent in the position -- its duties and powers -- as opposed to the work actually performed by a quondam holder of that position.” Galloza v. Foy, 389 F.3d 26, 31 (1st Cir. 2004). The defendants do not develop any argument, however, as to why the determination of "the attributes inherent in the - 19 - position" are a function solely of the formal job descriptions, no matter what other evidence might reveal about the job duties for that position. This variant of the potential argument is therefore waived for lack of development. See United States v. Gonsalves, 859 F.3d 95, 112 n.7 (1st Cir. 2017) ("[W]e don't have to parse [the argument] out any further because the argument is undeveloped, and undeveloped arguments are waived."). IV. For the reasons set forth above, the District Court's order denying summary judgment based on qualified immunity that is at issue in this interlocutory appeal is affirmed. - 20 -