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A Florida businessman embroiled in a $500 million dispute over ownership of the Miss America pageant urged a federal judge on Monday not to impose sanctions for allegedly filing false documents, claiming the records in question were withdrawn promptly once concerns about their authenticity were raised.

The hearing in the Southern District of Florida focused on whether attorney Craig T. Galle and his client, Glenn Straub, misrepresented operating agreements for Miss America Competition LLC and Miss America IP LLC, two entities tied to the century-old pageant. Straub is contesting ownership claims brought by plaintiff Robin Fleming, who asserts she is the rightful owner of the organization.

Straub’s counsel, Terri Meyers, told U.S. District Judge Donald M. Middlebrooks that the documents were withdrawn after receiving a Rule 11 letter from Fleming’s attorneys. “They demanded we withdraw those documents, which we did,” Meyers said. “They filed the motion for sanctions anyway, which is against the rule.”

Fleming’s attorney, Benjamin Chew, countered that Straub and Galle had a history of submitting misleading documents across multiple jurisdictions, including state courts in Florida and New Jersey and bankruptcy proceedings. He requested financial sanctions between $5 million and $10 million, along with a striking of the counterclaim and an adverse jury instruction regarding the documents’ validity.

The operating agreements in dispute were initially purportedly drafted and signed in December 2022. Fleming contends the documents were actually created in April 2024 when Straub presented them. Galle testified that the originals were lost when his laptop was stolen in Ecuador in January 2023, leading him to retype the agreements in August 2023 when Straub considered adding his daughter to the company.

Straub, who has a fifth-grade education and dyslexia, testified that he relies heavily on advisers to navigate complex legal documents. On the stand, he frequently referred to “whatever the document says” when questioned about the agreements and board meeting minutes. He acknowledged signing the documents but denied wrongdoing, saying, “I don’t think I did something wrong.”

Emails presented during the hearing highlighted discrepancies in dates and signatures. One email from Galle to Straub’s assistant contained unsigned operating agreements dated December 28, 2022, which were later sent to Fleming’s attorneys fully executed. Fleming’s counsel argued that these inconsistencies support claims of fraudulent representation.

The legal fight follows Straub’s Chapter 11 filing for Miss America Competition LLC in November 2024. Straub claims he is the legitimate owner of the debtor entity and the nondebtor Miss America IP LLC, which holds the intellectual property. Fleming maintains that Straub has never had rightful ownership, alleging he manipulated her into buying assets under misleading terms and later altered repayment agreements in 2023.

Fleming’s complaint also recounts a pattern of threats and aggressive behavior, including verbal threats and notices of termination from employment. The case remains active as the court weighs motions regarding sanctions and document authenticity.

The dispute involves multiple parties, including Palm Beach Polo Inc., Galle, and Straub’s assistant Kathleen Fialco. While Galle has since settled, litigation continues against Straub and his entities. The case is being closely watched due to the high-profile nature of the Miss America brand and the complex interplay of bankruptcy and intellectual property claims.

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