UNITED STATES DISTRICT COURT FOR THE DISTRICT OF COLUMBIA

JAMES E. PIETRANGELO, II,

Plaintiff,

v. No. 18-cv-1943 (DLF)

REFRESH CLUB, INC., et al.,

Defendants.

MEMORANDUM OPINION

Plaintiff James E. Pietrangelo, II, proceeding pro se, brought this suit against Refresh Club,

Inc. and The Wing DC, LLC (together, “The Wing”) seeking monetary, injunctive, and declaratory

relief for alleged violations of the D.C. Human Rights Act of 1977,

et seq,

Dkt. 1. On September 29, 2023, the Court granted Pietrangelo summary judgment on his public-

accommodation and advertising claims. The Court then ordered supplemental briefing on the

potential mootness of Pietrangelo’s requests for equitable relief and, on February 27, 2024, held a

bench trial on compensatory and punitive damages. The parties completed their post-trial briefing

on May 25, 2024. For the reasons that follow, the Court concludes that (1) Pietrangelo’s claims

for injunctive and prospective declaratory relief are moot; (2) Pietrangelo’s claim for retrospective

declaratory relief is not moot; and (3) Pietrangelo is entitled to $1,000 in compensatory damages

and $2,000 in punitive damages.

I. BACKGROUND

The Court recapitulated the facts of this case at length in its earlier Memorandum Opinion

and reiterates here only the facts essential to this opinion. See Pietrangelo v. Refresh Club, Inc.,

No. 18-cv-1943,

, at *1–3 (D.D.C. Sept. 29, 2023). On June 4, 2018, Plaintiff James E. Pietrangelo, II, a 53-year-old man, applied for membership at The Wing DC, a workspace

styling itself as “women-only.” Pl.’s Statement of Material Facts as to Which There Is No Genuine

Issue ¶¶ 1, 4–5, 8–9, 27, Dkt. 127-1. At that time, The Wing “did not have a formal, written

membership policy and its practice was to admit as members only women and non-binary

individuals,” Defs.’ Statement of Material Facts ¶ 10 (Defs.’ Counter-Statement of Material Facts),

Dkt. 128-3, so Pietrangelo was not admitted, see

; Helen Dally Dep. at 20:6–7, 17–18, Dkt.

101-6. On August 20, 2018, Pietrangelo, proceeding pro se, filed a complaint against The Wing,

seeking monetary, injunctive, and declaratory relief for alleged violations of the D.C. Human

Rights Act of 1977 (“DCHRA”),

et seq. Compl. at 30–31, Dkt. 1. As

relevant here, Pietrangelo seeks (1) “a declaration or declarations that Defendants’ . . . practices

violated/violate” the DCHRA and “were/are unlawful discriminatory practices”; (2) “temporary,

preliminary, and permanent injunctions enjoining Defendants’ unlawful discriminatory practices

in the future, and remedying Defendants’ unlawful discriminatory practices in the past—including

injunctions requiring Defendants to grant Plaintiff membership in The Wing”; and (3)

compensatory and punitive damages.

.

On August 30, 2018, The Wing adopted a “formal, written membership

policy . . . provid[ing] that all applicants will be evaluated based on their commitment to The

Wing’s mission, regardless of their perceived gender or gender identity.” Defs.’ Counter-

Statement of Material Facts ¶¶ 11–12. The Wing then moved to dismiss Pietrangelo’s claims

under Rule 12(b)(1), arguing in relevant part that The Wing’s new gender-neutral membership

policy rendered his claims for declaratory and injunctive relief moot. See Mem. of L. in Supp. Of

Defs.’ Mot. to Dismiss at 19, Dkt. 11. The Court disagreed, holding that Pietrangelo’s claims for

declaratory and injunctive relief were not moot under the “voluntary cessation” exception: namely,

2 “it [was] not ‘absolutely clear’ that The Wing’s newly inaugurated membership policy w[ould]

prevent further gender discrimination.” Pietrangelo v. Refresh Club, Inc., No. 18-cv-1943,

, at *9 (D.D.C. June 4, 2019).

In March 2020, almost a year after the Court’s denial, The Wing closed its Washington,

D.C. location. Defs.’ Counter-Statement of Material Facts ¶ 16. The Wing later “ceased all

business operations effective August 30, 2022” at all locations.

. On December 8, 2022,

The Wing—under its corporate name Refresh Club, Inc.—dissolved in Delaware. See Decl. of

Geoffrey Raicht Ex. A, at 2, Dkt. 135-2. Both parties subsequently moved for summary judgment,

see Dkts. 127, 129, and the Court granted in part and denied in part both motions on September

29, 2023, see Dkts. 133, 134. Specifically, the Court granted Pietrangelo summary judgment on

his public-accommodation and advertising claims, denied The Wing summary judgment on the

disparate-impact claim, and granted The Wing summary judgment on the aiding-and-abetting

claim. See Pietrangelo,

, at *4–15.

In its opinion, the Court sua sponte raised the potential mootness of Pietrangelo’s claims

for prospective relief, acknowledging that “circumstances ha[d] indisputably changed” since the

denial of The Wing’s 2019 motion to dismiss on mootness grounds. See

. The Court

“thus order[ed] the parties to submit additional briefing and any appropriate affidavits on the issue

of whether Pietrangelo’s claims for prospective relief are now moot.”

The parties subsequently

briefed the issue, see Dkts. 135–136, and the Court heard argument on October 27, 2023.

Also, the Court’s September 29, 2023 opinion denied both parties’ motions for summary

judgment on punitive damages. See

at *15–16. Pietrangelo waived his right to a jury trial, see

Notice of Waiver of Jury Trial, Dkt. 139, and the Court held a bench trial on February 27, 2024 to

determine whether Pietrangelo is entitled to compensatory and/or punitive damages. See Min.

3 Order of Feb. 28, 2024. He seeks $4 million in compensatory damages ($2 million for each

violation) and $8 million in punitive damages ($4 million for each violation). See Mem. in Supp.

of Pl.’s Damages at 1, Dkt. 141.

At the bench trial, the Court limited the evidence to the summary-judgment record and

Pietrangelo’s trial testimony. See Bench Trial Tr. at 75:7–76:2. Although Pietrangelo sought to

introduce evidence of online third-party comments, the Court excluded this evidence because it

was not disclosed in discovery. See

at 75:19–20. Following trial, the parties submitted post-

trial briefs. See Dkts. 143, 144, 145, 146, 148.

II. LEGAL STANDARD

Under Federal Rule of Civil Procedure 12(h)(3), “[i]f the [C]ourt determines at any time

that it lacks subject-matter jurisdiction, [it] must dismiss the action.” “Federal courts lack

jurisdiction to decide moot cases because their constitutional authority extends only to actual cases

or controversies.” Conservation Force, Inc. v. Jewell,

(D.C. Cir. 2013)

(quoting Iron Arrow Honor Soc’y v. Heckler,

(1983)); see also U.S. Const. art.

III, § 2. To ensure an actual controversy remains extant, mootness must be assessed at “all stages

of review, not merely at the time the complaint is filed,” and the Court may raise the issue of

mootness sua sponte. Decker v. Nw. Env’t Def. Ctr.,

(2013) (cleaned up); see

Munn Bey v. Dep’t of Corr.,

, 6 n.5 (D.D.C. 2011). If the court determines that

it lacks jurisdiction because a claim is moot, the court must dismiss the claim. Fed. R. Civ. P.

12(b)(1), 12(h)(3).

A case or claim is moot “when the issues presented are no longer live or the parties lack a

legally cognizable interest in the outcome.” Schmidt v. United States,

(D.C.

Cir. 2014) (quoting Larsen v. U.S. Navy,

(D.C. Cir. 2008)). This occurs when, for

4 example, “intervening events make it impossible to grant the prevailing party effective relief,”

Lemon v. Geren,

(D.C. Cir. 2008) (cleaned up), or when the Court’s decision

“will neither presently affect the parties’ rights nor have a more-than-speculative chance of

affecting them in the future.” Aref v. Lynch,

(D.C. Cir. 2016) (quoting Am. Bar

Ass’n v. FTC,

(D.C. Cir. 2011)).

“The initial ‘heavy burden’ of establishing mootness lies with the party asserting a case is

moot, but the opposing party bears the burden of showing an exception applies.” Honeywell Int’l,

Inc. v. Nuclear Regul. Comm’n,

(D.C. Cir. 2010) (citations omitted). One well-

established exception is based on “a party’s ‘voluntary cessation’ of the challenged activity. As a

general rule, a defendant’s ‘voluntary cessation of allegedly illegal conduct does not deprive [a

court] of power to hear and determine the case.’” ABA,

(quoting County of Los

Angeles v. Davis,

(1979)). “Voluntary cessation will only moot a case if ‘there

is no reasonable expectation . . . that the alleged violation will recur’ and ‘interim relief or events

have completely and irrevocably eradicated the effects of the alleged violation.’”

(quoting

Davis,

). The defendant carries the “heavy” burden of showing “that there is no

reasonable expectation that the wrong will be repeated.” United States v. W.T. Grant Co.,

(1953) (cleaned up).

Further, compensatory damages “are intended to redress the concrete loss that the plaintiff

has suffered by reason of the defendant’s wrongful conduct.” State Farm Mut. Auto. Ins. Co. v.

Campbell,

(2003) (cleaned up). These include “economic damages, which are

a concrete loss, and damages for pain, suffering, and mental anguish for which the amount of

damages is not a sum certain.” Dumpson v. Ade, No. 18-cv-1011,

, at *7

(D.D.C. Aug. 9, 2019) (cleaned up). “[C]ompensatory damages must be proven and cannot be

5 presumed,” Peyton v. DiMario,

(D.C. Cir. 2002) (citing Carey v. Piphus,

, 263–64 (1978)), and the plaintiff bears the burden of proving such relief is warranted,

see Jean-Baptiste v. District of Columbia,

(D.D.C. 2013).

Punitive damages “punish[] unlawful conduct and deter[] its repetition.” BMW of N. Am.,

Inc. v. Gore,

(1996). Punitive damages are “to be awarded only in cases of

outrageous or egregious wrongdoing where the defendant has acted with evil motive, actual

malice, or in willful disregard for the rights of the plaintiff.” Halcomb v. Woods,

(D.D.C. 2011) (quoting Rosenthal v. Sonnenschein Nath & Rosenthal, LLP,

(D.C. 2009)). The plaintiff carries “this high substantive burden” of “prov[ing] egregious

conduct and the requisite mental state by clear and convincing evidence.”

(quoting Rosenthal,

). Any such award is subject to the Due Process Clause of the Fourteenth

Amendment, which prohibits “the imposition of grossly excessive or arbitrary punishments on a

tortfeasor.” State Farm,

.

III. ANALYSIS

A. Equitable Relief

The Court has an “affirmative” and continuing “obligation to ensure that it is acting within

the scope of its jurisdictional authority . . . which includes the obligation to consider the possibility

of mootness.” Lindell v. Landis Corp. 401(k) Plan,

(D.D.C. 2009) (cleaned

up). The Wing argues that Pietrangelo’s claims for injunctive and declaratory relief are moot

“because (1) there is no longer a live controversy between the parties; (2) there is no reasonable

expectation the alleged violations will recur; and (3) interim events have completely and

irrevocably eradicated the effects of the alleged violations.” Defs.’ Supp. Mem. at 1, Dkt. 135.

The Wing thus seeks the dismissal of Pietrangelo’s claims for injunctive and declaratory relief.

6 See id. at 8. Pietrangelo disputes the mootness of his claims, principally arguing under the

voluntary-cessation exception that The Wing could reopen and continue to operate in a

discriminatory manner. See Pl.’s Br. Re Injunctive & Declaratory Relief at 2–9, Dkt. 136. The

Court will dismiss as moot Pietrangelo’s claims for injunctive and prospective declaratory relief,

but it will not dismiss as moot Pietrangelo’s claims for retrospective declaratory relief.

1. Injunctive Relief

Pietrangelo seeks “temporary, preliminary, and permanent injunctions enjoining

Defendants’ unlawful discriminatory practices in the future, and remedying Defendants’ unlawful

discriminatory practices in the past—including injunctions requiring Defendants to grant Plaintiff

membership in The Wing.” 1 Compl. at 30. Based on The Wing’s closure and later dissolution,2

the Court will dismiss as moot Pietrangelo’s claim for injunctive relief.

The Wing has provided sufficient evidence “that there is no reasonable expectation that the

wrong will be repeated,” United States v. W.T. Grant Co.,

(1953) (cleaned up),

1 Although Pietrangelo’s prayer for injunctive relief seeks to “remedy[] . . . practices in the past,” Compl. at 30, the relief sought is entirely prospective: namely, Pietrangelo seeks future membership in The Wing, see

(“including injunctions requiring Defendants to grant Plaintiff membership in The Wing”). “[A]n injunction is a prospective form of relief, designed to prevent future injury,” and Pietrangelo seeks to prevent future discrimination in membership. Nigerians in Diaspora Org. Ams. v. Key, No. 19-cv-3015,

, at *11 (D.D.C. Mar. 3, 2021). 2 The Court rejects The Wing’s principal argument that Pietrangelo’s injunctive-relief claim is moot because of The Wing’s adoption of a new membership policy that evaluates applicants “based on their commitment to The Wing’s mission, regardless of their perceived gender or gender identity.” Defs.’ Supp. Mem. at 5;

at 4–5 (citing White v. Bank of Am., N.A.,

(D.D.C. 2016)). As discussed supra, the Court previously rejected this argument because it went to the heart of the parties’ dispute—i.e., whether The Wing’s written membership policy violated the DCHRA facially or in effect. Pietrangelo,

, at *8. Moreover, adjudicating mootness on this basis would effectively require the Court to enter a declaratory judgment in The Wing’s favor that the written membership policy did not violate the DCHRA. White,

. It would amount to an “advisory opinion[]” years after The Wing’s closure that “cannot affect the rights of the litigants in the case before it.” St. Pierre v. United States,

(1943) (per curiam).

7 and “events have completely and irrevocably eradicated the effects of the alleged violation,” ABA,

(cleaned up). In the Court’s September 29, 2023 decision, it directed the parties

to City of Erie v. Pap’s A.M.,

(2000), in which the Supreme Court held that

“[s]imply closing [a business] is not sufficient to render [a] case moot.” In that case, the City of

Erie, Pennsylvania enacted a law banning public nudity, and Pap’s A.M., the owner of a “nude-

dancing establishment” called “Kandyland,” challenged the law, seeking injunctive and

declaratory relief.

at 282–84. The Pennsylvania Supreme Court “conclud[ed] that the public

nudity provisions of the ordinance violated [Pap’s] rights to freedom of expression.”

.

The City of Erie petitioned for a writ of certiorari, and “[s]hortly thereafter, Pap’s filed a motion

to dismiss the case as moot, noting that Kandyland was no longer operating as a nude dancing

club, and Pap’s was not operating a nude dancing club at any other location.”

. Noting

that “this is not a run of the mill voluntary cessation case,” the Supreme Court rejected Pap’s

mootness argument for several reasons: (1) “Pap’s is still incorporated under Pennsylvania law,”

meaning “it could again decide to operate a nude dancing establishment”; (2) Pap’s failed, “despite

its obligation to the Court, to mention a word about the potential mootness issue in its brief in

opposition to the petition for writ of certiorari . . . even though . . . Kandyland was closed”; (3) the

City of Erie “has an ongoing injury because it is barred from enforcing the public nudity provisions

of its ordinance” under the Pennsylvania Supreme Court decision; and (4) the Court had “an

interest in preventing litigants from attempting to manipulate the Court’s jurisdiction to insulate a

favorable decision from review.”

at 287–88.

This case is distinguishable from City of Erie on each of the bases identified by the Supreme

Court. First, unlike Pap’s, which was “still incorporated under Pennsylvania law” at the time of

its mootness challenge, City of Erie,

, The Wing is dissolved under Delaware law.

8 The Wing provided the Court with a certificate of dissolution from the State of Delaware,

confirming that Refresh Club, Inc., the sole member of The Wing D.C. LLC, was dissolved on

December 8, 2022. See Decl. of Geoffrey Raicht Ex. A. The Wing also offers a declaration from

Geoffrey Raicht, the Chief Restructuring Officer of Refresh Club, Inc., and Raicht states that

“[d]efendants ceased all business operations effective August 30, 2022,” Refresh Club, Inc.’s

“board of directors [and shareholders] voted to dissolve RCI’s corporate existence,” “[d]efendants

have no assets,” and “[t]he wind down and liquidation of [d]efendants is complete.” Decl. of

Geoffrey Raicht ¶¶ 4–8. According to The Wing, “[t]here is no plan or intention to revive The

Wing.” Defs.’ Supp. Mem. at 5 (citing Raicht Decl. ¶ 8). The Court also takes notice that The

Wing has not operated in Washington, D.C. for over four years or globally in the last two or so

years. Second, unlike Pap’s, the Court here finds no evidence that The Wing hid the ball on

dissolution. Indeed, The Wing’s summary-judgment briefing was upfront about ceasing

operations and filing for dissolution, which prompted the Court’s initial mootness inquiry. See

Defs.’ Counter-Statement of Material Facts ¶ 81, Dkt. 128-3; Defs.’ Statement of Material Facts

¶¶ 16–17. Third, Pietrangelo would not suffer “ongoing injury” within the meaning of City of Erie

if the Court finds his injunctive-relief claims moot. In City of Erie, a finding of mootness would

have “insulate[d] a favorable decision [in Pap’s favor] from review,”

, but there is

no such risk here because there is no “unvacated decision below” injuring Pietrangelo,

Pharmachemie B.V. v. Barr Lab’ys, Inc.,

(D.C. Cir. 2002). Fourth, the Court

raised mootness sua sponte, pouring cold water on the theory that The Wing is “manipulat[ing]

the Court’s jurisdiction,” especially given the Court’s summary-judgment grant in Pietrangelo’s

favor. City of Erie,

.

9 Pietrangelo provides a litany of counterarguments, but the Court remains unpersuaded. He

argues (1) The Wing “or their successor(s) . . . have the method and means to easily re-open The

Wing”; (2) Raicht “was curiously described as The Wing’s sole remaining director, and was even

more curiously titled . . . ‘Chief Restructuring Officer’” not “Chief Dissolution Officer”; (3) The

Wing has an “active” incorporation in the State of New York; (4) The Wing’s “obstructive

‘conduct during proceedings’ in this case” should cast doubt on the “veracity of The Wing’s

purported dissolution”; (5) “the timing of The Wing’s announced closure” reflects deception

because The Wing’s “August 30, 2022 announced closure came on the heels of [Pietrangelo’s]

July 27, 2022 motion for sanctions”; and (6) “the larger societal importance of addressing the

injunctive-relief claim at issue . . . counsels not finding that claim moot.” Pl.’s Br. Re Injunctive

& Declaratory Relief at 4–6.

Pietrangelo’s arguments are largely without factual or legal support, and some

arguments—especially (2), (4), and (5)—verge on the frivolous. The Court will briefly address

those arguments that have some weight. See Sun v. District of Columbia,

,

168 n.6 (D.D.C. 2015) (“[I]t is not the Court’s job to canvass the record for documents supporting

a pro se party’s position.”). As to (1), Pietrangelo offers nothing more than speculation that The

Wing’s parent company could reopen “even if in different buildings than before.” Pl.’s Br. Re

Injunctive & Declaratory Relief at 3–4. Even assuming The Wing’s parent company has

significant assets, see

that does not specifically undermine the veracity of the certificate of

dissolution and testimony from Raicht, nor does it counter the observable fact that The Wing’s

Washington D.C. location has remained closed for over four years. Even if the parent company

were to reopen The Wing—albeit under a different banner, the Court would lack jurisdiction over

the new entities, which would be nonparties. Ruling on Pietrangelo’s claim for injunctive relief

10 would amount to “an advisory opinion as to other potential cases, with no effect on the present

parties.” Pharmachemie B.V.,

(emphasis added).

As to (3), Pietrangelo suggests The Wing is not actually dissolved based on Refresh Club,

Inc.’s New York “Entity Information” page. This too lacks merit. True, on the website for the

New York Department of State Division of Corporations, Refresh Club, Inc.’s “Entity Status” is

described as “Active.” Decl. of James E. Pietrangelo, II Ex. 2 at 1, Dkt. 136-2. But upon further

inspection, the New York “Entity Information” page does not cast doubt on The Wing’s evidence

of its corporate dissolution. To start, the “Jurisdiction” listed is “Delaware,” and The Wing’s

corporate-dissolution statement is clear that The Wing is dissolved in that state.

Further, the

New York “Entity Information” page is outdated, as evidenced by the “Statement Status” listed as

“Past Due Date,” the latest filing occurring on January 15, 2020, and the “Chief Executive

Officer’s Name” listed as The Wing’s former CEO Audrey Gelman. See

The Court thus rejects

Pietrangelo’s suggestion that the New York “Entity Information” page “raises doubt[s]” as to the

“certificate of dissolution.” Pl.’s Br. Re Injunctive & Declaratory Relief at 5.

As to (6), the Court disagrees with Pietrangelo’s contention that “as in City of Erie . . . the

larger societal importance of addressing the injunctive-relief claim” counsels against mootness.

Pl.’s Br. Re Injunctive & Declaratory Relief at 6. Pietrangelo mischaracterizes City of Erie’s

reasoning. To the extent the Supreme Court considered factors besides the reasonable likelihood

of Pap’s reopening, the Court raised its “interest in preventing litigants from attempting to

manipulate the Court’s jurisdiction,” not the social importance of the underlying claims. City of

Erie,

. For the reasons stated supra, the Court flatly rejects any suggestion The

Wing seeks to improperly manipulate the Court’s jurisdiction.

11 In sum, The Wing has persuaded the Court that, based on its dissolution and cessation of

global operations, “it can be said with assurance that ‘there is no reasonable expectation’” that The

Wing will reopen and reinstitute its challenged membership policy. Davis,

(quoting United States v. W. T. Grant Co.,

(1953)). Further, now that The Wing

is defunct, the forward-looking “effect[]” of the challenged membership policy has been

“eradicated.”

Given The Wing’s dissolution, the Court lacks jurisdiction to enjoin The Wing

prospectively and will dismiss Pietrangelo’s claim for injunctive relief.

2. Declaratory Relief

Pietrangelo seeks “a declaration or declarations that Defendants’ above-alleged practices

violated/violate” the DCHRA and “were/are unlawful discriminatory practices.” Compl. at 30.

As the Court reads the complaint, Pietrangelo requests two different forms of declaratory relief.

First, he seeks prospective relief that The Wing’s membership policy as it exists (i.e., with the

August 2018 written membership policy in force) violates the DCHRA. Second, he seeks

retrospective relief that The Wing’s membership policy at the time Pietrangelo applied violated

the DCHRA. The Court will dismiss as moot Pietrangelo’s prospective claim but not his

retrospective claim.

i. Prospective Declaratory Relief

For much the same reason the Court will dismiss Pietrangelo’s claim for injunctive relief

as moot, the Court will dismiss his claim for prospective declaratory relief as moot. “In

determining whether a request for declaratory relief has become moot, ‘the question . . . is whether

the facts alleged, under all the circumstances, show that there is a substantial controversy, between

parties having adverse legal interests, of sufficient immediacy and reality to warrant the issuance

of a declaratory judgment.’” Conyers v. Regan,

(D.C. Cir. 1985) (quoting

12 Preiser v. Newkirk,

(1975)). Further, “the D.C. Circuit has indicated that where

a plaintiff seeks both declaratory and injunctive relief pertaining to unlawful agency action, and

where the latter has been mooted, an outstanding request for the former will not operate to bar

mootness.” Chavis v. Garrett,

, 36–37 (D.D.C. 2019) (cleaned up).

Pietrangelo requests a declaration that The Wing’s membership policy as a present and

forward-looking matter violates the DCHRA. But the Court simply cannot afford the requested

relief because the challenged membership policy no longer exists by virtue of The Wing’s

dissolution. See La Botz v. FEC,

(D.D.C. 2012) (“[I]f Article III’s case-

or-controversy requirement is to have any meaning, the court’s opinion must consist of something

more than helpful advice. It must be capable of remedying the plaintiff’s injury.”). A declaration

of present or forward-looking unlawfulness under the DCHRA would amount to an advisory

opinion because there is no “controversy of ‘sufficient immediacy and reality’ to warrant

declaratory relief.” Conyers,

(quoting Preiser v. Newkirk,

(1975)). Moreover, the Court’s mootness analysis under City of Erie applies with equal force here

because City of Erie adjudicated the mootness of both injunctive and prospective declaratory relief.

See City of Erie, 529 U.S. at 287–89. The Court will thus dismiss Pietrangelo’s claim for

prospective declaratory relief as moot.

ii. Retrospective Declaratory Relief

The Court will not, however, dismiss as moot Pietrangelo’s claim for retrospective

declaratory relief—i.e., a declaration that The Wing applied an unlawful membership policy at the

time of his application. “[C]ourts have held that plaintiffs may seek a retrospective declaratory

judgment—that is, declaratory relief premised on past harm—when the request is intertwined with

a claim for monetary damages that requires [the court] to declare whether a past constitutional

13 violation occurred.” Creamer v. District of Columbia, No. 22-cv-1874,

, at *1

(D.D.C. June 15, 2023) (cleaned up). This makes good sense: if a court holds that a plaintiff is

entitled to monetary damages, the court has, in effect, declared that the defendant invaded the

plaintiff’s legal rights. Cf. Uzuegbunam v. Preczewski,

(2021) (“When a right is

violated, that violation imports damage in the nature of it and the party injured is entitled to a

verdict for nominal damages.” (cleaned up)). As such, if a plaintiff’s claim for damages is not

moot, his claim for retrospective declaratory relief as to the same injury is unlikely to be moot.

In Coleman ex rel. Bunn v. District of Columbia, for example, plaintiffs brought a Takings

Clause challenge against a District of Columbia tax-sale law on behalf of “all District property

owners who suffered” under the law, seeking monetary damages and a declaratory judgment.

, 71–72 (D.D.C. 2015). After the filing of the lawsuit, the D.C. Council passed two

temporary amendments to the District’s tax-sale law. See

at 72–73. The plaintiffs moved for

class certification, seeking to certify a “damages class” and “declaratory relief class,” and the

District of Columbia opposed the motion, arguing in relevant part that “the Declaratory Relief

Class lacks standing because it contains members whose claims would be rendered moot by the

enactment of amendments to the District’s tax-sale law.”

at 73–77. The court disagreed

because the plaintiffs “defin[ed] the Declaratory Relief Class” as “identical to the Damages

Class”—i.e., the “Declaratory Relief Class” sought “a retrospective declaratory judgment because

its claims [were] intertwined with a claim for monetary damages.”

at 74–75 (cleaned up).

As in Coleman, Pietrangelo’s claim for retrospective declaratory relief is not moot.

Pietrangelo seeks a backward-looking declaration that The Wing violated the DCHRA when it

evaluated his membership application. In other words, he seeks redress for “a completed violation

of a legal right” under the DCHRA, and The Wing’s subsequent dissolution does not nullify the

14 redressability of this past injury. Uzuegbunam,

. Further, neither party suggests

Pietrangelo’s claim for compensatory damages is moot. Pietrangelo’s retrospective-declaratory-

relief claim is “intertwined with [his] claim for monetary damages,” as evidenced by the Court’s

September 29, 2023 memorandum opinion, which held that Pietrangelo is entitled to, at the very

least, compensatory damages because The Wing violated the DCHRA. Coleman,

(cleaned up). Indeed, the Court’s prior order implicitly granted the retrospective declaratory

relief to which Pietrangelo is lawfully entitled. See Hailu v. Morris-Hughes, No. 22-cv-20,

, at *4 (D.D.C. Feb. 23, 2023) (“Because [the plaintiff] has standing to seek

compensatory damages, and resolving his claims may require this court to declare whether the

[defendant] violated his constitutional rights, [the plaintiff] is entitled to seek declaratory

judgments determining that the [defendant] acted unlawfully.”). The Court thus concludes that the

claim for retrospective relief is not moot. Accordingly, the Court will order the parties to file a

proposed declaration.

B. Damages

On June 26, 2024, the Court held a bench trial to determine whether Pietrangelo is entitled

to any compensatory and/or punitive damages. Pietrangelo contends he is entitled to $12 million

in damages. See Mem. in Supp. of Pl.’s Damages at 1, Dkt. 141. The Wing argues that he is

entitled to, at most, nominal damages, see Defs.’ Post-Trial Br. at 1–2, Dkt. 144. Based on the

evidence in the record and trial testimony, the Court concludes that Pietrangelo is entitled to $1,000

in compensatory damages and $2,000 in punitive damages.

1. Compensatory Damages

The DCHRA authorizes a court to “grant any relief it deems appropriate,”

-

1403.16, including “the payment of compensatory damages,”

§ 2-1403.13. A plaintiff may

15 recover compensatory damages for “humiliation, embarrassment, and emotional pain and

suffering,” even if he suffers “no physical or medical injury.” Sumes v. Andres,

(D.D.C. 1996). And “[a] finding of humiliation and embarrassment flows naturally from a

finding of discrimination.”

In calculating compensatory damages for a DCHRA violation, courts typically assess what

is “appropriate” based on the testimony of the plaintiff and the surrounding context.

Courts

also consider whether aggravating factors warrant enhanced damages. See Joel Truitt Mgmt, Inc.

v. D.C. Comm’n on Hum. Rts.,

, 1010 (D.C. 1994). But “the weight of the evidence

must support the damages given.” Jean-Baptiste,

.

Compensatory damages that are based on non-economic harms, such as humiliation,

embarrassment, and emotional pain, can be difficult to quantify. For assistance in determining the

value of such intangible harms, the Court is guided by the decisions of other courts. In Sumes, for

example, a court in this District awarded $10,000 to a plaintiff based on a doctor’s refusal to give

her prenatal care because she was deaf. Sumes, 938 F. Supp. at 12–13. The award was based in

part on the plaintiff’s testimony that the defendant’s actions made her feel “angry, irritated,

dismissed, and like less of a person.”

. It was also based on the surrounding context:

namely, the plaintiff was pregnant; she was in the defendant’s office for her first visit to an

obstetrician-gynecologist; and she was “in the examining room disrobed, except for a hospital

gown, from the waist down.”

These circumstances bolstered the plaintiff’s claim for

“emotional damages,” but they were not deemed sufficiently “egregious” to warrant any

enhancement.

at 13 n.5.

For a showing of discrimination without any aggravating circumstances, other courts have

awarded similar amounts. Federal courts in New York, for example, follow the lead of the New

16 York City Human Rights Commission and award $1,000 in damages when plaintiffs have not

“establish[ed] any particular damage other than what a decent and reasonable individual would

suffer when faced with such ignorant behavior.” Kreisler v. Second Ave. Diner Corp., No. 10-cv-

7592,

, at *14 (S.D.N.Y. Sept. 11, 2012) (quotation omitted), aff’d,

(2d Cir. 2013); see, e.g., Shariff v. Radamar Meat Corp., No. 11-cv-6369,

,

at *4 (E.D.N.Y. Feb. 14, 2014) (awarding to a disabled plaintiff unable to access a supermarket

$1,000 in compensatory damages for “mental anguish and emotion[al] distress, including . . .

depression, humiliation, [and] embarrassment”), report and recommendation adopted as modified,

(E.D.N.Y. Mar. 31, 2014)); Shalto v. Bay of Bengal Kabob Corp., No. 12-cv-

920,

, at *10 (E.D.N.Y. Feb. 6, 2013) (reducing damages award from $25,000 to

$1,000 for a disabled plaintiff unable to access a restaurant), report and recommendation adopted

as modified,

(E.D.N.Y. Mar. 7, 2013)). Although the New York City Human

Rights Commission occasionally awards damages over $5,000, those cases involve “extreme

circumstances,” such as insults or demeaning conduct toward the plaintiff. Kreisler,

, at *15.

Aggravating circumstances often warrant a higher damages award. One such aggravator

warranted an award of $35,000 in Joel Truitt Management, Inc. 646 A.2d at 1010. In that case, a

landlord discriminated against a tenant who had AIDS, notifying the tenant in a written

memorandum that “trades people” would not come work on his apartment until he provided a

certificate from a “qualified health authority” that it was safe for them to enter. Id. at 1008. A key

driver of the damages award was an aggravating factor: namely, the landlord’s “untrue derogatory

statements.” Id. at 1010. Specifically, the D.C. Human Rights Commission “found no basis for

the [landlord’s] implied assertion” that the tenant “kept hypodermic needles in his apartment” or

17 otherwise permitted unsanitary conditions. Id. at 1010 n.6. The D.C. Court of Appeals affirmed

the damages award, concluding that the judge had not committed an abuse of discretion by

enhancing the award to $35,000, even though the Commission had awarded $20,000 in a factually

similar case. See id. at 1010.

But, as Sumes and Joel Truitt Management reflect, a damages award must be supported by

record evidence. In Jean-Baptiste, a jury awarded $3.5 million to a plaintiff who alleged sexual

harassment and retaliation by District of Columbia employees, in violation of both Title VII and

the DCHRA.

. Reviewing the award, the court granted remittitur because the

plaintiff’s “testimony regarding her injuries simply was not sufficient to support” an award that

large.

. Although the court credited the testimony of the plaintiff about her “stress,

anxiety, and depression,” it also noted that she “offered no testimony from a medical or

psychological professional regarding the impact the harassment and retaliation had on her physical

or mental health.”

Her only corroboration was the testimony of a co-worker that she looked

“stressed, frustrated, and kind of nervous.”

(cleaned up). The court held that the most the

plaintiff’s testimony could support was an award of compensatory damages of $350,000.

; see also Liberatore v. CVS N.Y., Inc.,

, 120–21 (D.D.C. 2001) (reducing a

damages award for emotional distress from $1.1 million to $200,000 because the plaintiff’s

“testimony alone does not provide the substantial evidentiary basis needed to warrant an award of

this amount”).

Here, Pietrangelo has established that The Wing violated the DCHRA’s public-

accommodation and advertising provisions. See Pietrangelo,

, at *7, 13. The

Court credits his testimony that his rejection based on his sex and The Wing’s advertising practices

caused “humiliation,” or a “feeling of being sort of demeaned.” Bench Trial Tr. at 18:12–14; see

18 Sumes,

(crediting the testimony of a plaintiff that suffering discriminatory

conduct made her feel “angry, irritated, dismissed, and like less of a person”). The Court also

credits his “great indignity and outrage” at The Wing for “thumbing [its] nose at the law and at

[his] rights under the [DCHRA] to not be discriminated against based on sex.” 3

at 18:19–20,

19:22–24. Such feelings “flow[] naturally from a finding of discrimination.” Sumes,

.

That said, Pietrangelo has not persuaded the Court that he suffered any additional harms

justifying an enhancement in compensatory damages. First, Pietrangelo offered no evidence that

The Wing’s practices caused acute harm to his mental health. Throughout his testimony,

Pietrangelo testified about his humiliation and embarrassment at a high level of generality, see,

e.g., Bench Trial Tr. at 18:9–23, but he offered no evidence that The Wing’s conduct caused

specific deleterious effects in his life. Without any such concrete details, Pietrangelo’s testimony

about his degree of embarrassment (e.g., facing “the darkest time” in his life) appeared exaggerated

and uncredible.

. When pushed by the Court, he also admitted that his mental health

did not get “to the point where [he] ever sought medical treatment.”

at 20:11–12. Similar to

Jean-Baptiste, the Court is limited in its ability to award enhanced damages when the only

evidence of emotional damages comes from the plaintiff’s “self-serving testimony,” not that of a

medical professional.

(cleaned up).

3 The Court asked the parties to brief whether Pietrangelo’s compensatory damages are time capped based on his limited residency (from 2018 to 2019) in Washington, D.C. See Bench Trial Tr. at 57:22–23. Ultimately, however, there is no need to prorate Pietrangelo’s damages because the Court does not credit his testimony about the economic value of lost opportunities at The Wing. In addition, it would not be reasonable (or even possible) to prorate Pietrangelo’s damages because the evidence he submitted in support of his claim of emotional injury is far too general in nature. See Jean-Baptiste,

.

19 Second, Pietrangelo did not offer any solid evidence about the value of opportunities

available at The Wing. He testified that, as a member of The Wing, he could have rubbed shoulders

with Hollywood A-listers, venture capitalists, and political figures. See

at 30:1–22, 31:2–25.

But this testimony was, at bottom, speculative and lacked a clear tangible benefit to his projects,

including screenwriting, producing, writing books, and pro se litigation. For example, the Court

did not find credible Pietrangelo’s testimony that he expected, as a member of The Wing, to

advance his career by handing a copy of his screenplay to a guest speaker like Reese Witherspoon.

See

at 35:17–36:12. Such speculation is not a proper basis for an award of compensatory

damages. See Zoerb v. Barton Protective Servs.,

, 470–71 (D.C. 2004).

Third, as The Wing effectively elicited on cross-examination, Pietrangelo took no efforts

to mitigate his damages. “Mitigation requires a party to take reasonable steps after it has been

injured to prevent further damage from occurring.” Adenariwo v. Fed. Mar. Comm’n,

(D.C. Cir. 2015). “[C]lassic examples of mitigation” include “procuring a substitute” and

“repairing harm that would otherwise cause consequential losses.”

The “injured party” must

take “beneficial steps to prevent further damages.”

On cross-examination, Pietrangelo more

or less admitted he took no steps to mitigate his damages after The Wing rejected his application.

See Bench Trial Tr. at 49:24–51:23. He testified that he tried to mitigate by bringing suit, see

at 51:9–10, but otherwise admitted that he did not seek to join any other coworking space despite

having toured ten in the area and did not seek mental-health treatment, see

at 20:10–12, 24:10–

18. He further explained that joining another coworking space would have been impracticable

because none could compete with The Wing’s offerings, including its “Danish decor” and “curated

art.” Id. at 25:16, 19. But the duty to mitigate does not require a perfect substitute, only a

“reasonable” one. Adenariwo,

. And the Court did not find credible Pietrangelo’s

20 testimony that The Wing’s superior aesthetics prevented him from joining another coworking

space with lesser features.

Fourth, Pietrangelo’s arguments based on allegedly derogatory comments are

unpersuasive. Specifically, Pietrangelo points to (1) Former CEO Audrey Gelman’s statement that

he is a “garden-variety kook” and (2) The Wing’s representation that he is a “serial litigant.” Mem.

in Supp. of Pl.’s Damages at 12. As to the former, Pietrangelo admits that he learned about the

“garden-variety kook” statement only during discovery. See at Pl.’s Mot. for Partial Summ. J. at

40, Dkt. 127. Pietrangelo offers no concrete evidence that the statement adversely affected him at

or around the time of his rejection from The Wing or at any time thereafter. And in any event,

Gelman made the statement privately to a Daily Beast reporter, and it was apparently not

published. As to the latter statement, the Court disagrees that the characterization of Pietrangelo

as a “serial litigant” is derogatory or untrue. This is not a case like Joel Truitt Management, Inc.

in which the defendant baselessly stated that the plaintiff had hypodermic needles strewn on his

apartment floor. See 646 A.2d at 1010 n.6. Here, in contrast, The Wing effectively elicited on

cross-examination that Pietrangelo has filed numerous pro se lawsuits in various jurisdictions. See

Bench Trial Tr. at 53:22–56:19. Indeed, Pietrangelo stated on direct examination that he wanted

to join The Wing, in part, to have a quiet place to write briefs for one of his other pro se cases. See

id. at 23:9–10, 53:25–54:9. As such, the “serial litigant” comment appears anchored in reality.

Finally, The Wing’s conduct, though illegal, was not aggravated. The conduct alleged here

falls far short of that in cases in which a defendant has placed a plaintiff in a particularly

humiliating or compromising situations. See, e.g., Sumes,

(plaintiff was refused

treatment while she was disrobed from the waist down, covered only by a hospital gown); Jean-

Baptiste, 931 F. Supp. 2d at 4–8 (plaintiff suffered repeated instances of degrading sexual

21 harassment over a period of at least five months). Pietrangelo identifies no such similar

aggravators and readily admitted on cross-examination that his embarrassment was “internal” and

not based on the conduct of a third party besides The Wing. Bench Trial Tr. at 64:10–13.

At bottom, Pietrangelo proved that The Wing’s denial of his application and advertising

practices constituted violations of the DCHRA. Humiliation and embarrassment naturally flow

from such discrimination. For those harms, this Court, following the lead of other courts,

concludes that Pietrangelo is entitled to $1,000 in compensatory damages. But Pietrangelo has

fallen short of proving any aggravating circumstances that warrant enhancing that award—

certainly not to the tune of his requested $4 million.

2. Punitive Damages

Under the DCHRA, “punitive damages are available in all discrimination cases . . . subject

only to the general principles governing any award of punitive damages.” Daka, Inc. v. Breiner,

(D.C. 1998) (cleaned up). A finding of discriminatory action alone is insufficient

to warrant a punitive damages award absent “[a] showing of evil motive or actual malice.” Arthur

Young & Co. v. Sutherland,

(D.C. 1993); see also Rogers v. Ingersoll-Rand

Co.,

(D.D.C. 1997) (“Punitive damages are properly awarded where the act of

the defendant is accompanied by fraud, ill will, recklessness, wantonness, oppressiveness, willful

disregard of the plaintiff's rights, or other circumstances tending to aggravate the injury.”). The

requisite mental state “need not . . . be proven by direct evidence, but may be inferred from all the

facts and circumstances of the case.” Daka,

(cleaned up).

Contrary to The Wing’s assertion, see Defs.’ Post-Trial Br. at 12, Pietrangelo has provided

sufficient mental-state evidence for an award of punitive damages. As the Court previously noted,

The Wing “launched a multiyear advertising campaign promoting itself as a ‘No Man’s Land,’

22 posted jokes about men to its social-media accounts, and did not offer any evidence that a cisgender

man was granted membership.” Pietrangelo,

, at *15. In addition, upon

learning that the New York City Commission on Human Rights opened a sex-discrimination

investigation against The Wing, Former CEO Audrey Gelman tweeted that “the Wing seems like

it’s gonna be O.K.: (Without men.)” and that the investigation has “only gotten [The Wing] more

press.” Pl.’s Statement of Material Facts ¶ 59(6), Dkt. 127-1. In the Court’s view, all this evidence

evinces a “willful disregard of the . . . rights” of men, who are a protected class under the DCHRA.

Rogers,

. Moreover, these statements undermine any defense that The Wing

“lacked awareness of the DCHRA’s prohibitions.” Pietrangelo,

, at *15 (citing

Kolstad v. Am. Dental Ass’n,

(1999)). Indeed, Gelman’s “garden-variety kook”

comment—though not relevant to compensatory damages—evinces The Wing’s continued failure,

even after the start of this litigation, to take seriously the antidiscrimination mandate of the

DCHRA. From this, the Court concludes that an award of punitive damages is appropriate to both

punish and deter The Wing and other would-be offenders for ignoring the DCHRA and mocking

those seeking to vindicate their civil rights.

As to the precise dollar amount, Pietrangelo seeks punitive damages double the value of

compensatory damages—i.e., $8 million for both DCHRA violations. See Mem. in Supp. of Pl.’s

Damages at 1. As a constitutional threshold, “few awards exceeding a single-digit ratio between

punitive and compensatory damages . . . will satisfy due process.” State Farm Mut. Auto. Ins. Co.,

. Given that the Court will award $1,000 in compensatory damages, an $8 million

award in punitive damages would undoubtedly violate the Due Process Clause—approximating a

8,000 multiplier.

23 The Court does, however, agree with Pietrangelo that a multiplier of two is reasonable.

“[A]n award of more than four times the amount of compensatory damages might be close to the

line of constitutional impropriety.”

(citing Pac. Mut. Life Ins. Co. v. Haslip,

, 23–

24 (1991)). As such, courts in other jurisdictions have approved a multiplier of one, or close to

one, in comparable discrimination cases. See, e.g., Roberts v. United Parcel Serv., Inc.,

(E.D.N.Y. 2015) (using 1-to-1 ratio for claim of violation of New York City

Human Rights Law); Bivins v. Wrap it Up, Inc., No. 07-cv-80159,

, at *8 (S.D.

Fla. Oct. 18, 2007) (using 1-to-1 ratio for claims of violations of

and Florida

Civil Rights Act); Rodriguez v. Gattuso,

(N.D. Ill. 1992) (awarding three-

fourths of the amount of compensatory damages for housing-discrimination claims in violation of

and 3604(b)).

On at least one occasion, however, a judge in this District has awarded punitive damages

with a multiplier of five for DCHRA violations. In Dumpson v. Ade, the plaintiff was the “first

female, African-American student government president at American University.”

, at *1. One of the defendants unleashed a maelstrom of racist comments online about the

plaintiff—including, “Racoons Rule, coons drool”; “Chimput!”; and “Waah, waah, Dats

Rayceez!”

. This harassment caused the plaintiff to “fear[] for her life and suffer[] both

physically and mentally.”

Her “academics and preparation for law school also suffered,” and

she missed exams and dropped her minor.

The plaintiff also “receiv[ed] regular psychiatric

counseling” and was diagnosed with and received treatment for Post Traumatic Stress Disorder,

“an eating disorder, depression, and anxiety.”

Given the defendants’ “outrageous conduct”

that “resulted in liability for intentional infliction of emotional distress,” the Court awarded the

plaintiff $101,429.28 in compensatory damages and $500,000 in punitive damages.

at *7–8.

24 That case is distinguishable from Pietrangelo’s. To start, as discussed supra, he presented no

mental-health evidence that could have revealed something about The Wing’s mental state. Nor

did he bring a claim for intentional infliction of emotional distress. And, in any event, the conduct

in Dumpson is far more egregious than that here. As such, a multiplier of five is not appropriate.

Given The Wing’s violations of the DCHRA, aggressive marketing as a non-male space,

and initial mockery of efforts to enforce antidiscrimination laws, the Court concludes that a

multiplier of two is reasonable and no greater than necessary to achieve the goals of retribution

and deterrence. The Court will thus award Pietrangelo $2,000 in punitive damages. 4

3. Reasonable Litigation Expenses

Pietrangelo seeks reasonable litigation costs in connection with this suit, but this request is

premature. See Mem. in Supp. of Pl.’s Damages at 25–26. Pietrangelo, as the “prevailing party[,]

may serve and file a bill of costs” and must do so “within 21 days after entry of judgment

terminating the case.” LCvR 54.1(a). The Court has not entered final judgment. When it does,

Pietrangelo will have twenty-one days to file a bill of costs.

4 The Wing notes that Pietrangelo did not introduce any evidence of The Wing’s net worth and that, in any event, The Wing is not an ongoing concern. See Defs.’ Post-Trial Br. at 12–13. Evidence of a defendant's net worth may be relevant to an award of punitive damages. See Jonathan Woodner Co. v. Breeden,

(D.C. 1995) (“[W]here a plaintiff seeks to recover punitive damages based on the wealth of the defendant, proof of the defendant’s current net worth is required.”). Here, however, Pietrangelo’s request for punitive damages is not based on The Wing’s wealth; rather, he focuses on the award’s traditional deterrence and retribution functions. See, e.g., Mem. in Supp. of Pl.’s Damages at 5. Nor does The Wing present any authority suggesting that lack of net-worth evidence is a bar to recovering punitive damages, and the Court is unaware of any such barrier. Cf. Murphy v. Islamic Republic of Iran,

, 79–83 (D.D.C. 2010) (awarding punitive damages against a defendant in default). And, in any event, the Court’s total damages award would not deplete The Wing’s remaining assets. See Decl. of Geoffrey Raicht ¶ 7, Dkt. 135-1 (“A nominal amount of money (approximately $6,000) remains in [Refresh Club, Inc.’s] bank account but any transfers out of this account have been frozen.”).

25 CONCLUSION

For the foregoing reasons, the Court dismisses as moot Pietrangelo’s claims for injunctive

and prospective declaratory relief but not his claim for retrospective declaratory relief. In addition,

the Court awards Pietrangelo $1,000 in compensatory damages and $2,000 in punitive damages.

A separate order consistent with this decision accompanies this memorandum opinion.

________________________ DABNEY L. FRIEDRICH United States District Judge July 12, 2024

26