Former NFL Players Association leader Lloyd Howell Jr. resigned after an outside investigator hired by the union received documents this week showing Howell charged the union for two visits to strip clubs, including a $738.82 car service that took him from the airport to one of the clubs.

The documents are union-approved expense reports and receipts, which ESPN began asking questions about hours before Howell abruptly resigned late Thursday night.

One receipt, obtained by ESPN, shows Howell was picked up in a sedan by a car service at Fort Lauderdale International Airport on Thursday, Nov. 2, 2023, at 10:26 p.m. The car’s first stop was at a nearby Miami Gardens address. The receipt shows only one other stop, nearly eight hours later.

At 6 a.m., the car dropped off Howell at his luxury condominium in Sunny Isles Beach, the receipt shows.

Later, a union finance worker noticed the car service’s exorbitant cost. The employee searched online for the Miami Gardens address, discovering it was Tootsie’s Cabaret.

The 76,000-square-foot venue bills itself as the world’s largest strip club — “full nude No. 1 rated.”

The employee flagged the receipt to the union’s travel department for a higher level of review, two people familiar with union operations told ESPN. The head of union travel then forwarded the documents to compliance for review by union lawyers, the sources said.

More than a year later, Howell and two union employees visited a strip club in Atlanta, according to the expense reports obtained by ESPN.

During this year’s NFLPA summit on Feb. 21, Howell accompanied the employees to the Magic City strip club for an outing that incurred $2,426 in charges including cash withdrawals, ranging from $200 to $525, from a club ATM, sources and documents show. They used two “VIP rooms.”

According to the expense report, the purpose of the strip club outing: “Player Engagement Event to support & grow our Union.”

The NFLPA summit is an annual event to foster leadership among players and young union employees.

One of the employees who accompanied Howell submitted expense reports for this outing, the documents show. Howell instructed the employee to file the expense reports, two sources familiar with the matter told ESPN.

The employee noted on a March 23 expense report: “$736 = This was the final amount I was charged to close the tab for both secluded sections for our Player Members. This included Food, Alcoholic Drinks, fees, taxes, and gratuity.” No players’ names are listed on receipts or the reports.

Documents show four cash withdrawals were flagged with “alerts,” apparently referring to potential reimbursement violations.

Howell could not be immediately reached for comment. A union spokesperson declined to comment.

Ronald C. Machen, a lawyer for Wilmer Hale, was hired by a special committee of players to investigate Howell’s activities. “Our work continues,” a source close to Machen told ESPN.

Federal labor laws are strict when it comes to a union’s expenses and reimbursement actions; the laws aim to protect union members whose dues fund all of the operations, unlike what happens in a corporate environment.

Bob Stropp, a widely respected veteran labor lawyer, told ESPN that the car service reimbursement is “the kind of sexy thing that gets the attention of the [U.S.] Department of Labor.”

“That’s pretty horrible,” said Stropp, 77, the former general counsel of the United Mine Workers of America. “That’s unbelievable. I don’t know how you get around that. It’s hard to believe that anyone would be that stupid.”

The NFLPA has its own set of strict guidelines on reimbursements of all kinds, but particularly for entertainment, former union officials say. A former union employee said that there are no specific exclusions for venues, like a strip club, within the union’s “entertainment” category.

“But I don’t think anyone in their right mind would think that is an optically good scenario,” the former employee said. “In light of this, clearly that aspect of the policy should be revisited.”

Howell was elected union president in 2024 and was paid $3.6 million last year. He has lived in Miami since 2019; records show he paid $6.8 million in September 2019 for a three-bedroom condominium in the Porsche Design Tower in Sunny Isles Beach. The building features “in-unit garages for owners to house their prized vehicles.” Like his neighbors in the 132-unit building, Howell has access to an elevator to deliver his car directly to his residence.

Questions about expense reports submitted for strip clubs have come up in Howell’s career before. His prior employer, Booz Allen, questioned him about a strip club visit on company time, too.

In 2015, Howell and a senior vice president visited a Manhattan, New York, strip club, where they racked up thousands of dollars for the night’s entertainment, a former Booz Allen executive told ESPN. Afterward, Howell’s colleague sought reimbursement on an expense report, which was referred to the firm’s compliance lawyers.

The colleague was fired, and Howell reprimanded, the executive said. At the time, Howell was a defendant in a sexual discrimination and retaliation lawsuit filed by a Booz Allen partner. Booz Allen settled — for an undisclosed sum — the case that had alleged Howell and the company denied female employees leadership roles and excluded them from certain career opportunities provided to men.

Another former Booz Allen executive told ESPN the company was concerned about disciplining Howell while the lawsuit was active. A year later, Booz Allen promoted Howell to be its chief financial officer, with the support of the CEO and executives at the Carlyle Group, the sources said.

In his resignation statement Thursday night, Howell, 59, said: “It’s clear that my leadership has become a distraction to the important work the NFLPA advances every day. For this reason, I have informed the NFLPA Executive Committee that I am stepping down as Executive Director of the NFLPA and Chairman of the Board of NFL Players effective immediately. I hope this will allow the NFLPA to maintain its focus on its player members ahead of the upcoming season.”

Howell’s resignation was made on his own and surprised some members of the NFLPA’s 10-person executive committee, who tried repeatedly to persuade him not to leave the union during a lengthy conference call Thursday night, according to people briefed on the call.

The resignation came after several recent reports from ESPN and the “Pablo Torre Finds Out” podcast:

• Earlier on Thursday, ESPN reported on the Booz Allen sexual discrimination and retaliation lawsuit that involved Howell and whether the players who voted for him to lead the NFLPA were aware of it.

• In May, ESPN reported that the FBI is investigating the financial dealings of the union and the MLB Players Association related to a multibillion-dollar group-licensing firm, OneTeam Partners. According to sources, the report triggered a special committee of players’ union to hire Machen to review Howell’s activities as the executive director.

• Last week, ESPN reported that Howell is working as a paid, part-time consultant for the Carlyle Group, one of the league-approved private equity firms seeking ownership in NFL teams.

• ESPN also reported last week that Howell struck a confidentiality agreement with the NFL six months ago that hid the details of the January arbitration decision from players, including a finding that league executives urged team owners to reduce guaranteed player compensation. The 61-page ruling was published by the “Pablo Torre Finds Out” podcast on June 24.

On Sunday, the union’s executive committee backed Howell in a message sent to membership, saying it had “established a deliberate process to carefully assess the issues that have been raised and will not engage in a rush to judgement.”

As recently as late Wednesday night, two executive committee members gave a strong endorsement to Howell’s leadership and vision for the NFLPA in a joint interview with ESPN. “We felt great about the process,” one of them said. “We are 100 percent behind Lloyd.”