Jane MusgraveWellington pageant operator Robin Fleming says relationship began to unravel after she rejected Straub’s sexual advances.
Fresh from being cleared of criminal charges accusing him of punishing an ex-girlfriend by slapping liens on her houses, Wellington developer Glenn Straub is embroiled in an ongoing multimillion-dollar legal battle over his claimed ownership of the Miss America pageant.
In the legal fight that has played out in state, federal and bankruptcy courts, Straub is accused of stealing the ownership of the iconic century-old contest from a Wellington woman who headed both Miss Florida USA and Miss California USA competitions.
Straub, meanwhile, accuses the woman, Robin Fleming, of using trickery and deceit to parlay her job as someone he hired to run the pageant to falsely claim that she is the rightful owner.
“This case raises extensive allegations of fraud, coercion, and legal manipulation in connection with the ownership of Miss America,” U.S. District Judge Donald Middlebrooks wrote, summing up the claims in the dueling lawsuits.
Attorneys representing Fleming and Straub are less reserved.
“This case involves a fraud monstrous in scope and harm,” Fleming’s team of lawyers wrote in their opening salvo of the 101-page federal lawsuit filed in March. “The perpetrator of the fraud is Glenn F. Straub, a 78-year-old self-proclaimed ‘billionaire’ with a long history of fraud in business dealings and predation upon women.”
Straub’s lawyers bristled at allegations that he mistreats women.
The former Atlantic City casino owner, who built a successful career buying distressed businesses, was trying to do the right thing by saving the financially struggling pageant, his attorneys said in court papers.
“He wanted to see the Miss America organization and its positive message of women’s empowerment continue and perhaps rise to even greater heights,” they wrote.
Instead, they claim, he got stung by an unscrupulous Fleming, who devised a “scheme by which she intended to wrestle control of the Miss America companies from Straub in hostile fashion.”
She is seeking $500 million in damages. He is seeking at least $20 million.
‘A house of cards’
The level of animosity between the two sides was on vivid display on Sept. 8 during a routine hearing before U.S. Magistrate Judge William Matthewman.
Attorney Justin Chretien, who represents Fleming, claimed Straub with the help of his longtime attorney, Craig Galle, created fraudulent documents to make it appear the developer owned the pageant. In the lawsuit, the Washington, D.C., lawyer is accusing Straub and Galle of conspiracy in violation of the Florida Racketeering Influenced and Corrupt Organizations Act.
“It’s a house of cards,” Chretien told Matthewman. “It is a chain of events that began with a decision by Mr. Straub to take control of the Miss America companies from Ms. Fleming when he was supposed to be her banker.”
Despite Straub’s claim of ownership, he has had nothing to do with the pageant, which began in 1921. Since Fleming bought the enterprise nearly three years ago, she has organized the competitions, including the most recent one in Orlando that concluded Sept. 7 with Miss New York Cassie Donegan crowned as 2026 Miss America.
Miami attorney Todd Levine, who began representing Straub and Galle in July after their other lawyers withdrew, agreed with Chretien’s characterization of the case.
“It is a house of cards but it was constructed by Ms. Fleming,” Levine said during last week’s court hearing. “She is not the owner and she knows she is not the owner. … Ms. Fleming is engaging in a fraud upon the court.”
‘Friends with benefits’?
The path that led to such acrimony began simply enough — with a chance meeting in late 2021 at the Stallion restaurant in the Palm Beach Polo & Country Club in Wellington, according to Fleming’s suit.
Fleming had recently moved into the 2,250-acre community that Straub bought in 1993 for $27 million at a government auction. The two hit it off and began meeting at the restaurant regularly, she claims.
Having been involved in the Miss America pageants since 2008 and having organized competitions in California and Florida since 2017, she told Straub about her passion for the contests.
A fashion designer with a marketing degree from DePaul University, she considered herself an entrepreneur. From 2005 to 2015, she operated La Casa Hermosa in Wellington, selling wedding and party dresses and pageant gowns, which were regularly used by contestants.
She and Straub talked about business deals. He offered her a job editing a magazine he owned. She declined. She and her children were invited to events on his 185-foot mega-yacht, the 4 Roses.
She claims their relationship began to sour in September 2022 when she rejected his suggestion that they begin having sex — or “friends with benefits,” as she said he described it.
“I like our relationship exactly as it is, fun business chatter/ambitions with a smattering of humor … I am too conservative for anything else,” she told him in a text that she included in the suit.
Inexplicably, after her rejection, a deal he crafted to loan her $20 million to buy the Miss Universe pageant, fell through, she said.
But, the chance to buy the Miss America competition surfaced soon after. Straub again offered to loan her money to buy a pageant.
To buy the national beauty contest, she needed $4.1 million to cover the pageant’s outstanding debts. Straub agreed to set up a $4.1 million reserve fund and she agreed to repay the money in three years. With the agreement in hand, she pursued the purchase of the competition, she claims.
In January 2023, the board of the Miss America pageant welcomed Fleming as the new owner, voted to dissolve and she took over, she claims.
She spent the next year planning and then overseeing the 2024 Miss America and Miss America Homecoming contests and began planning the 2025 events, she said in her lawsuit. She paid off a $515,000 loan from Straub, who had covered one of the outstanding debts of the former pageant owners.
“There is no evidence — no documents, emails or texts from Straub or Galle (or anyone for that matter) — that challenges her ownership until March 2024,” her attorneys wrote.
That month, Fleming refused Straub’s request to serve as a plaintiff in a lawsuit he filed against the board of the property owners association at the polo club.
For Straub, it was the final blow, attorneys for Fleming claim.
“Straub was enraged by Ms. Fleming’s rejection of his request to have sex in September 2022, her success in paying off the note to Palm Beach Polo in February 2023, and her rejection of his unethical request to serve as his proxy in litigation on March 14, 2024,” her attorneys wrote. “He had no leverage over her.”
So, with the help of Galle, he plotted to destroy her, they claim.
Straub saw himself as pageant owner
Documents were altered. Corporations were formed. Threats were made. Lawsuits ultimately were exchanged.
In lawsuits filed by Straub in both state and federal court, he makes no mention of how he met Fleming. He acknowledges they discussed business deals.
But, he vehemently rejects Fleming’s claims that he ever offered to loan her money, that he wanted to have sex with her or asked her to help him in the lawsuit against the property owners association.
Most importantly, he said, it was always clear that he would be the owner of the Miss America contest and she would run the day-to-day operations as the company CEO, manager and president.
“At no time was there any discussion or agreement that Fleming would have any ownership stake in any of the Miss America companies,” Straub said in the federal lawsuit.
By the end of 2023, Straub, through Palm Beach Polo, had paid at least $862,425 toward Miss America expenses, he said.
When he learned in March 2024 that she was telling people she was the owner, he began to investigate her. He claims he uncovered misdeeds.
She had changed the passwords on company financial records and bank accounts so he couldn’t access them. She had taken at least $200,000 from the company for her personal use.
On April 15, 2024, he fired her. Less than a week later, he sued her in Palm Beach County Circuit Court for $20 million.
Past treatment of women
In response, Fleming launched a campaign to discredit him, Straub claims. She accused Straub of engaging in sex crimes and criminal activities, and of lying about his ownership of the pageant.
The lawsuit she eventually filed against Straub is peppered with allegations other women have made against him.
Prominently mentioned are the criminal charges Straub faced after prosecutors said he filed $77,000 in false liens against homes owned by his 41-year-old ex-girlfriend, Jessica Nicodemo, after she broke up with him.
The felony charges were dismissed in August by a Broward County judge, who was assigned the case after all of the judges in Palm Beach County recused themselves. While they are not required to state a reason, many had ties to a former judge on his defense team.
Broward County Circuit Court Judge Tim Bailey ruled that Straub couldn’t be charged because the liens were filed by his company, not him, Straub said in a statement, celebrating his victory.
Fleming’s attorneys said Straub’s past treatment of women was highlighted to underscore how he operates. Straub insisted it was an effort to embarrass him.
“Fleming hoped that by defaming Straub she would prevail over Straub in the ‘court of public’ opinion and get Straub to back down from asserting his rightful ownership over the Miss America companies,” his attorneys wrote in the federal lawsuit.
For her part, Fleming claims Straub engaged in similar tactics, launching what they labeled “a blitzkrieg of personal attacks.” He held Zoom calls with the organizers of state beauty pageants, accusing her of being dishonest and corrupt and insisting that he, not Fleming, owned the pageant.
In hopes of clearing up the confusion that rocked the pageant world, the former Miss America chair and board members in May 2024 emailed a letter to state directors. In it they said they had voted unanimously to transfer the organization to Fleming because they trusted her abilities, according to her lawsuit.
She remained at the helm, they said in the email.
But the former board’s efforts to calm state directors was short-lived.
Short-lived bankruptcy petition
In November 2024, weeks before the 2025 Miss America pageant was to be held in Orlando, Straub filed a Chapter 11 petition in U.S. Bankruptcy Court, saying that the pageant was $4.1 million in debt.
Fleming responded, saying the petition was a ruse. Straub wasn’t the owner of the pageant and therefore couldn’t file the petition, her attorneys wrote in court filings. Further, she said, the pageant wasn’t operating in the red.
“The purpose of the petition is to sow chaos and confusion so that the competition does not take place in the hopes of bankrupting Miss America, which is otherwise not subject to financial distress,” her attorneys wrote.
Less than two weeks later, Straub withdrew the petition, saying he didn’t know the competition’s debts had been paid because Fleming had concealed the information from him.
But, the lull in the litigation also proved to be temporary.
In April, Fleming sued Straub in federal court. Straub responded by filing a countersuit against her.
The state court lawsuit is now on hold until the federal lawsuit is resolved. A trial is tentatively scheduled for March.
