Cruz v. UIA

• Court: Court of Appeals for the First Circuit
• Decided: December 3, 2025
• Docket: 23-2011
• Status: Published

Opinion

United States Court of Appeals For the First Circuit

No. 23-2011

REYNALDO CRUZ,

Plaintiff, Appellant,

v.

UNIÓN INDEPENDIENTE AUTÉNTICA DE LOS EMPLEADOS DE LA AUTORIDAD DE ACUEDUCTOS Y ALCANTARILLADOS; PUERTO RICO AQUEDUCT AND SEWER AUTHORITY; JENNIFFER A. GONZÁLEZ-COLÓN, in her official capacity as Governor of the Commonwealth of Puerto Rico,*

Defendants, Appellees.

APPEAL FROM THE UNITED STATES DISTRICT COURT FOR THE DISTRICT OF PUERTO RICO

[Hon. Pedro A. Delgado-Hernández, U.S. District Judge]

Before

Barron, Chief Judge, Thompson and Gelpí, Circuit Judges.

Matthew B. Gilliam, with whom Milton L. Chappell, Ángel J. Valencia, Veronica Ferraiuoli-Hornedo, National Right to Work Legal Defense Foundation, Inc., and Estudio Legal Ferraiuoli, PSC were on brief, for appellant.

José-Enrico Valenzuela-Alvarado, with whom Mariangeli Mercado-Torres and Valenzuela-Alvarado, LLC were on brief, for appellee Unión Independiente Auténtica de los Empleados de la Autoridad de Acueductos y Alcantarillados.

* Pursuant to Federal Rule of Appellate Procedure 43(c)(2), Governor Jenniffer A. González-Colón is automatically substituted for former Governor Pedro R. Pierluisi-Urrutia. Alberto Tabales-Maldonado, with Erika Berríos Berríos, Lady E. Cumpiano, and Schuster LLC on brief, for appellee Puerto Rico Aqueduct and Sewer Authority.

Francisco J. González-Magaz, with whom Omar Andino Figueroa, Solicitor General of Puerto Rico and Francisco González P.S.C. were on brief, for appellee Jenniffer A. González-Colón, in her official capacity as Governor of the Commonwealth of Puerto Rico.

December 3, 2025 BARRON, Chief Judge. In this appeal, Reynaldo Cruz

("Cruz") seeks review of the dismissal of claims that he brought

in the United States District Court for the District of Puerto

Rico against three defendants: his employer, the Puerto Rico

Aqueduct and Sewer Authority ("PRASA"); Unión Independiente

Auténtica de los Empleados de la Autoridad de Acueductos y

Alcantarillados ("UIA"), of which Cruz was formerly a member; and

Jenniffer A. González-Colón ("Governor"), in her official capacity

as Governor of the Commonwealth of Puerto Rico.1 The District

Court dismissed the claims as moot. We remand for further

proceedings not inconsistent with this opinion, while retaining

jurisdiction over the appeal.

I.

In 2017, Cruz brought suit under 42 U.S.C. § 1983 against

the three defendants. His complaint alleged the following facts.

The Puerto Rico Labor Relations Act ("PRLA"), codified

at P.R. Laws Ann. tit. 29, § 61 et seq., allows public employers

to enter into "all-union" and "maintenance of membership"

bargaining agreements with labor organizations. Id. § 69(1)(c).

As defined in the Act, all-union agreements require all employees

Cruz's complaint named Ricardo Antonio Rosselló Nevares, in 1

his official capacity as the Governor of Puerto Rico, as a defendant. Pursuant to Federal Rule of Appellate Procedure 43(c)(2), Rosselló Nevares was automatically substituted by his successor, Pedro R. Pierluisi-Urrutia, who was later substituted by his successor, Jenniffer A. González-Colón.

- 3 - to be members of a given labor organization as a condition of

employment, id. § 63(7), and maintenance of membership agreements

require employees who are union members at the time a collective

bargaining agreement is executed to maintain membership as a

condition of continued employment, id. § 63(8). PRLA further

allows employers to "deduct[] any sum of money" from employees'

wages "for the payment of dues to a labor organization

when . . . required by the terms of a collective bargaining

contract." Id. § 69(1)(b).

Consistent with those provisions, the 2011 collective

bargaining agreement ("CBA") between PRASA and UIA makes

membership in UIA a condition of employment and details the

initiation fees and membership dues that PRASA must withhold from

each employee's pay and remit to UIA.

Cruz became a member of UIA when he began his employment

with PRASA in about 1992. In 2016, he sent letters to both UIA

and PRASA notifying them of his resignation from UIA and his

objection to continuing to pay union dues that would be used for

"political, ideological, and other nonbargaining expenditures."

As relevant here, in support of the latter, he relied on the

Supreme Court of the United States's decision in Abood v. Detroit

Board of Education, 431 U.S. 209 (1977). In Abood, the Court held

that a public employer may, consistent with the First Amendment,

require employees who are not union members to pay fair-share

- 4 - fees -- that is, fees collected for the purpose of "contribut[ing]

to the cost of collective-bargaining activities," id. at 237, but

not "for the expression of political views," id. at 235.

In response, PRASA and UIA -- acting pursuant to the CBA

and the PRLA -- rejected Cruz's requests to resign and to only pay

dues arising from UIA's collective bargaining expenses.

Accordingly, PRASA continued deducting the full amount of dues

from Cruz's pay and remitting them to UIA.

This suit followed. For relief, Cruz sought: (1) a

declaration that PRASA and UIA violated his federal constitutional

rights; (2) a declaration that the above-described provisions of

the PRLA and related provisions of the CBA violated the First

Amendment of the U.S. Constitution by allowing public employers to

require employees to maintain union membership as a condition of

employment and to impose dues payments on employees following their

resignation from the union; (3) a permanent injunction against

enforcement of those requirements; (4) restitution of and

compensatory damages for dues withheld from Cruz's pay since his

resignation in 2016, plus interest; (5) nominal damages, plus

interest; and (6) costs and attorneys' fees.

In its answer to Cruz's complaint, PRASA asserted a

cross-claim against UIA based on the CBA. In that claim, PRASA

alleged that UIA was liable for any monetary damages pursuant to

- 5 - a "hold-harmless" provision in the CBA.2 The cross-claim is not

at issue in this appeal.

While Cruz's claims were pending, the Supreme Court

overruled Abood in its decision in Janus v. American Federation of

State, County, and Municipal Employees, 585 U.S. 878, 930 (2018).

Shortly thereafter, the District Court entered a show-cause order

regarding Janus's impact on Cruz's pending suit. In response, the

Governor conceded that the PRLA provisions in question were

unconstitutional under Janus and that Cruz was therefore entitled

to his requested relief. For their parts, UIA and PRASA argued

that Janus did not resolve the pending claims. PRASA also went on

to explain that, consistent with an Opinion Letter issued by the

Puerto Rico Secretary of Justice, it had accepted Cruz's

resignation and ceased withholding dues from his pay. It further

stated: "[A]t this time, PRASA has no objection to the entry of a

prospective Declaratory Judgment as the one entered in Janus

regarding the unconstitutionality of the dispositions of [the PRLA

provisions] which, in light of the U.S. Supreme Court's holdings

in Janus, infringe upon plaintiff's freedom of speech rights."

2 That provision states: "The Union agrees to indemnify or exonerate PRASA for any amount of dues that PRASA deducted in compliance with [Article VII of the CBA -- which requires that PRASA deduct union dues from employees --] and that PRASA could be held liable to restitute to any employee or group of employees as a result of a judgment of decision that orders it as a result of a cause attributable to the Union."

- 6 - Cruz later filed a motion for summary judgment in which

he listed his compensatory damages request as $525.00 (the amount

of dues withheld from his pay following his resignation), plus

interest. Shortly thereafter, UIA filed a motion, pursuant to

Federal Rule of Civil Procedure 67,3 seeking leave to deposit with

the court the $525.00 Cruz had requested, plus $94.68 in interest

and $1.00 in nominal damages. That deposit, which UIA described

as a "request and/or deposit of tender payment," was sought to be

made "with a full and explicit reservation of [UIA's] rights and

without prejudice to all" of "UIA's defenses and claims."

Days later, UIA and PRASA each filed a motion in

opposition to Cruz's motion for summary judgment. Each asserted

that Cruz's requests for prospective relief were moot because UIA

and PRASA had recognized Cruz's resignation from UIA and ceased

collecting union dues from his pay following Janus. As to Cruz's

request for monetary relief, UIA alone argued that the request had

become moot following UIA's Rule 67 motion. It stated:

[Cruz] calculates that [post-withdrawal] dues and fees totaled $525 and seeks interest on that amount. UIA does not contest these calculations and has sought leave of the Court to consign with the Clerk's Office through a

3 That Rule permits a party, in a case in which "any part of the relief sought is a money judgment or the disposition of a sum of money," to "deposit with the court all or part of" such funds "by leave of the court." Fed. R. Civ. P. 67(a). Funds deposited with the court pursuant to Rule 67 must be withdrawn "in accordance with 28 U.S.C. §§ 2041 and 2042 and any like statute." Fed. R. Civ. P. 67(b).

- 7 - check for the full amount of damages sought, including nominal damages and interest, without any conditions attached. . . . UIA's unconditional tender of this cashier's check satisfies all of Plaintiff's retrospective claims, and his damages claim is therefore moot . . . .

(Citations omitted.)

The District Court denied UIA's Rule 67 motion because

that motion "d[id] not provide for an unconditional deposit, as it

[wa]s made with a full and explicit reservation of rights, without

prejudice to all of UIA's defenses and claims." The District Court

stated, however, that "UIA . . . may refile an updated check

without conditions by September 19, 2023." When UIA did not timely

respond, the District Court ordered as follows:

UIA requests dismissal on account of mootness. By September 27, 2023, it shall inform whether it unconditionally tendered plaintiff a check corresponding to the union fees deducted from his wages after he resigned from the union plus interest, or intends to unconditionally deposit with the court a check in that amount.

UIA then filed a motion in response to that order requesting the

District Court "to take notice of [UIA's] compliance with" the

order, and it deposited the funds in question with the court.

Shortly thereafter, the District Court issued an opinion

explaining that all the claims must be dismissed as moot. As to

Cruz's claims for prospective declaratory and injunctive relief,

the District Court concluded that they were moot because there was

- 8 - no longer "a substantial controversy of sufficient immediacy and

reality to warrant" such relief and "the challenged measures no

longer adversely affect[ed] the plaintiff's primary conduct." As

to Cruz's claims for monetary relief, the District Court recognized

that "a claim for damages will keep a case from becoming moot."

(Citation modified.) Nonetheless, the District Court noted that

"UIA requested authorization to deposit in court -- and

deposited -- the amount corresponding to union dues and fees

deducted from plaintiff's wages."

Following the District Court's entry of judgment

dismissing the claims as moot, Cruz filed a motion to alter and

amend the judgment under Federal Rule of Civil Procedure 59(e).

In that motion, he requested that the District Court "enter a

declaratory judgment . . . adjudicating his legal claims and

entitlement to the UIA deposit." Absent such a judgment, Cruz

argued, he "c[ould not] seek or obtain the UIA deposit" from the

court. The District Court denied the motion, explaining that UIA

had "deposited the money that plaintiff requested" in response to

the court's order "laying out side-by-side unconditional tendering

of the money to plaintiff and depositing the corresponding amount

in court," and that, under those circumstances, "the money is

[Cruz's] for the asking."

This timely appeal followed.

- 9 - II.

Cruz asks us to vacate the District Court's Rule 67 order

permitting UIA to deposit funds with the court, vacate the court's

dismissal of the case, and direct the District Court to grant

Cruz's motion for summary judgment and enter judgment awarding him

declaratory and monetary relief. There is no dispute that Cruz's

claims are moot insofar as he seeks prospective relief. As to

Cruz's claims for monetary relief or a declaratory judgment

regarding the defendants' past conduct, Cruz argues that they are

not moot because "[n]othing in the District Court's order or

judgment declared or otherwise adjudicated Cruz's legal

entitlement to relief or to the funds deposited in the court

registry." We disagree.

It is settled law that, on appeal, "the ruling on [a]

Rule 59(e) motion merges with the prior determination, so that the

reviewing court takes up only one judgment." Banister v. Davis,

590 U.S. 504, 509 (2020); see Rivers v. Guerrero, 605 U.S. 443,

454 (2025). Here, we cannot read the District Court's

determination in its ruling on the Rule 59(e) motion that the funds

were "[Cruz's] for the asking" other than as a judgment that Cruz

is entitled to the funds. Accordingly, the premise of Cruz's lead

argument for challenging the dismissal of his claims as

moot -- namely, that he cannot obtain his requested monetary relief

- 10 - because no judgment entitles him to it -- is mistaken, as the

judgment in his case does entitle him to it.

Even though, "having secured a favorable judgment"

regarding his entitlement to the funds, Cruz would appear to have

"no reason to contest" on appeal the District Court's "subordinate

findings," Field v. Mans, 157 F.3d 35, 41 (1st Cir. 1998), he

contended otherwise at oral argument. He contended that neither

his claim for monetary relief nor his claim for a declaratory

judgment regarding the defendants' past conduct is moot because,

even if the District Court's judgment entitles him to the funds at

issue, he may be unable to seek "prevailing party" attorneys' fees

pursuant to 42 U.S.C. §§ 1983 and 1988 unless the District Court

also determines that he is entitled to those funds because his

First Amendment rights were violated. At oral argument, an issue

arose regarding whether Cruz waived this argument regarding the

bearing, if any, of attorneys' fees on the mootness analysis.

With respect to appellate waiver, we do not agree that

Cruz waived this ground for arguing that his claims are not moot.

As one basis for challenging the validity of the District Court's

Rule 67 order, Cruz argued that UIA should not have been permitted

to "misuse . . . Rule 67 to evade liability and entry of judgment

for Cruz," thereby "depriving him of the opportunity to seek

attorneys' fees." (First citing Buckhannon Bd. & Care Home, Inc.

v. W. Va. Dep't of Health & Hum Res., 532 U.S. 598, 602-03 (2001);

- 11 - and then quoting Lutter v. JNESO, 86 F.4th 111, 135 (3d Cir. 2023)

("[W]here a live controversy remains, a defendant who would

otherwise be liable for attorney's fees should not be able to

wiggle out on the basis of a spurious claim of mootness.").)

Though admittedly limited, this argument is sufficient to avoid a

finding of waiver. See United States v. Dunbar, 553 F.3d 48, 63

n.4 (1st Cir. 2009) (deeming argument not waived where the

appellant identified relevant facts and cited case law in support

of his position).

Nonetheless, the District Court did not address the

prevailing party issue below or how it might bear on the mootness

issue. Accordingly, we remand to the District Court for

consideration of this ground for challenging its dismissal of the

claims based on their being moot, insofar as it determines that

any such basis for challenging the dismissal has not been waived.

III.

In accordance with the foregoing, we remand for further

proceedings not inconsistent with this opinion, while retaining

- 12 -