Miss America is embroiled in legal drama weeks before the 2025 competition

• The Miss America Organization is in a legal battle just weeks before the 2025 competition.
• CEO Robin Fleming sued Glenn F. Straub on November 28, as both say they own the organization.
• Straub filed for bankruptcy for Miss America, complicating the ownership dispute.

Miss America 2025 is just weeks away, and a legal battle over who owns the organization is playing out behind the scenes.

The 103-year-old competition has had several leadership controversies in the last decade, but this matter centers on Robin Fleming and Glenn F. Straub, who both purport to own Miss America.

In a sweeping, 32-cause complaint obtained by Business Insider, Fleming accused Straub, his lawyer, his company, and one of his employees of fraud, defamation, and trademark infringement.

Her lawsuit came days after Straub filed for bankruptcy on November 22. In a letter to Miss America board members, Straub wrote that Fleming was using the organization's scholarship fund to pay her legal fees, which was "putting Miss America in financial and legal jeopardy." He also said that the 2025 competition, scheduled for December 31 to January 3, will continue as planned.

Fleming said in her complaint that Straub's bankruptcy filing was fraudulent because he does not own the organization and Miss America Corporation, LLC, has no debt. She said Straub was attempting to sow "further chaos and confusion" amid their legal battle.

She told BI on Thursday that "Miss America has always been an activist" and believes "justice will prevail" in her case. "I just feel very strongly that this is a case about standing up and having your voice heard," she added.

"Robin Fleming's Miss America competition is going strong and will be fully successful," her attorney Gene Rossi said in a statement to BI. "Mr. Straub's litigation tricks are nothing more than shiny objects. All sound and fury with no meaning."

When asked for comment on this story, a representative for Straub pointed BI to the court's decision on Wednesday to dismiss Fleming's case without prejudice because of its length. The order allows Fleming to refile her complaint before December 20, which she told BI on Thursday that she intends to do.

Here's a timeline of all the legal drama detailed by Fleming and Straub's complaints.

2021: Robin Fleming and Glenn Straub connected

Fleming, who told BI she's in her 50s, and Straub, 78, briefly met at a charity event in 2008. Still, the two formed a professional friendship in 2021 at Palm Beach Polo Country Club, a luxury gated community in Florida that Straub owned and where Fleming was a resident.

Straub "presented as a wealthy and elderly man in his mid-70s keenly interested in her passion for businesses that empowered women and her passion for the pageant industry."

Summer 2022: Fleming tried to buy the Miss Universe Organization

Straub offered to finance the $20 million purchase of the Miss Universe Organization with Fleming "as owner and him as banker."

Fleming agreed to the proposition and made her interest known to the organization, providing Straub's name after it requested a call with her banker. The call never occurred, and it was announced in October 2022 that the Miss Universe Organization had been sold to Anne Jakrajutatip.

Fleming learned in 2024 that the Miss Universe Organization ceased its negotiations with her after learning Straub, according to her suit, had "allegedly choked a 22-year-old young woman in 2012 at a polo match."

Straub was arrested and charged with criminal battery. He filed a civil action against the woman for libel and slander. Both the civil and criminal cases were dismissed and closed.

September 15, 2022: Straub asked Fleming to be "friends with benefits."

During dinner together, Straub asked Fleming if they could become "friends with benefits."

Fleming texted Straub the following day, saying, "I like our relationship exactly as it is, fun business chatter/ambitions with a smattering of humor… I am too conservative for anything else."

Straub replied, "Check," and "never asked the question again."

December 30, 2022: Fleming purchased Miss America.

Fleming said she bought Miss America's assets on behalf of Miss America Competition, LLC and Miss America IP, Inc., using three documents created by Straub's attorney, Craig Galle, who she used at Straub's suggestion.

Shantel Krebs signed one of the agreements on December 30, officially selling the organization's assets to Fleming.

Straub's company paid off a Small Business Administration loan for Miss America to help the purchase proceed, his only official role in the acquisition.

Fleming also said she attended the closing meeting alone.

2022 - March 2024: Fleming appeared to operate Miss America without incident

Following the acquisition, Fleming said that Krebs and the Miss America board formally welcomed her as the organization's "new owner" and publicly referred to her as its CEO at events and in the media.

Fleming said she operated as Miss America's CEO and owner for over a year without complaints from Straub.

In a January 2024 text included in the suit, Straub asked Fleming how he should introduce himself as the Miss America 2024 pageant, suggesting "banker."

That same month, according to the lawsuit, Straub attacked a talent judge at Miss America 2024 because he was a Black man talking to a white woman.

Straub admitted in texts to Fleming that the attack was racially motivated, her suit states.

March 15-16, 2024: Straub told Fleming he was "shutting down Miss America"

Straub's threat came a day after Fleming declined to serve as his proxy in a lawsuit against board members of their gated community.

Straub told Fleming he wanted to end Miss America because she "cannot be controlled" and the organization is a "waste of time." He also said Fleming was a "failure," "over the hill," and that he would bring her children into the "public humiliation" and send letters to all the Miss America state directors saying she was mentally ill.

The following day, Straub sent Fleming a letter notifying her of her "Temporary Suspension and Investigation" by the "Miss America Competitions, LLC." Fleming said the letterhead featured typos in both the company name and the spelling of Fleming's name.

Fleming said Straub also threatened to tie her up in "three years of civil litigation" unless she gave him "total control of Miss America" and promised to "always be subservient" to him.

April 12, 2024: Straub gave Fleming what she says is a fraudulent Operating Agreement for Miss America Competition, LLC.

Fleming said Straub presented three different versions of the document created by Galle and dated December 28, 2022, between April and August.

Her legal team said metadata for one of the documents indicated it was created on August 25, 2023.

April 15, 2024: Straub tried to fire Fleming.

Fleming's suit said Straub texted her on April 12 to tell her she was fired as Miss America's CEO.

It added that he intended to email the Miss America state directors and tell them she was stealing money from the organization, which Fleming said was defamatory.

Her suit also states that he sent her a "Termination Notice" on April 15, which Fleming rejected in a written statement on April 16.

April 25, 2024: Straub filed a lawsuit against Fleming in Palm Beach, Florida.

Straub's complaint said Fleming had never been an "owner" of any Miss America entity and sued her for breach of fiduciary duties and obligations, "at will" employment agreement, temporary and permanent injunctive relief, and trademark infringement.

His complaint sought $20 million in damages.

April 29, 2024: Straub said he was Miss America's owner in a letter to staffers.

Straub sent a letter to Miss America directors and licensees in late December 2022 stating that he had "purchased all the assets of the former Miss America Organization."

He also said he hired Fleming to run Miss America and terminated her "after we received damaging information and conducted an extensive audit of her conduct while working with the organization."

In response to the letter, Krebs and other former Miss America board members told licensees and directors via email they had "voted unanimously to transfer the assets to Robin Fleming."

Straub also hosted Zoom meetings with Miss America licensees and contractual partners in May, during which he said he was Miss America's owner and had fired Fleming as CEO.

July 29, 2024: Straub said he planned to file for bankruptcy on Miss America's behalf.

According to a court docket reviewed by BI, Straub and Fleming were ordered to hold a "conciliation conference" to discuss his state-level lawsuit against her.

In her lawsuit, Fleming said Straub used the meeting to "directly threaten, intimidate and extort" her. She said Straub told her he wanted to "shut down Miss America," called himself "Hamas" and Fleming "Israel," and said he was Hitler.

Her complaint also said that Straub said he "intended to file for bankruptcy on behalf of her Miss America" during the meeting.

Fall of 2024: Fleming said Straub made defamatory statements about her

Fleming said Straub sent additional letters to state executive directors in September saying he had fired her, and, in November 2024, he publicly said she was funding her legal defense through Miss America's scholarship fund.

Her suit described his statements as defamatory and led to potential business deals to fall through.

Notably, the complaint said the "organizers of the iconic Macy's Thanksgiving parade withdrew their invitation to have Miss America participate in the parade, which has been a yearly tradition since the 1940s."

November 22, 2024: Straub filed a bankruptcy petition on behalf of Miss America.

Straub filed for Chapter 11 bankruptcy in the Southern District of Florida on behalf of Miss America Competition, LLC.

Fleming filed an emergency response to the bankruptcy filing on November 25, saying the bankruptcy was "a 'scorched earth' litigation strategy to attempt to sabotage the upcoming Miss America Competition and cause reputational harm to Ms. Fleming."

In the response, Fleming said Straub could not file for bankruptcy for Miss America Corporation because she is its sole member, manager, and owner.

November 28, 2024: Fleming filed a complaint against Straub, Galle, Kathleen A. Fialco, and Palm Beach Polo, Inc. in the Southern District of Florida.

Fleming's suit lists 32 causes of action, including fraud, defamation, and more. She is seeking $500 million in damages for herself and Miss America.

In her complaint, she said she was the rightful owner of Miss America and provided a timeline for its purchase, details of Straub's involvement, and evidence that Straub and his attorney created false documentation to show he owned it.

Fleming's case was dismissed on December 4, 2024, without prejudice, with the court requesting Fleming's lawyers condense their complaint.

Fleming told BI on Thursday that she would file a new version of the suit before the new December 20 deadline.