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Trump Social Media Firm Sues Ex-Co-Founder, Claims He Gambled Away Company Cash in Wild Slot Machine Spree

X Strategies, the Florida social media firm that powers some of President Donald Trump's most-followed social media accounts, is taking its former co-founder Derek Utley to federal court, accusing him of quietly draining at least $5 million from the company to fund a jet-set lifestyle and a staggering gambling habit, according to POLITICO.

The company filed a 34-page complaint September 18 in U.S. District Court in West Palm Beach against Utley and his former girlfriend Anna Weisheimer.

Co-founded by Trump adviser Alex Bruesewitz, X Strategies runs the Trump War Room and Team Trump accounts on X and helps manage the president's TikTok presence.

Utley, X Strategies' former chairman and chief financial officer, allegedly had exclusive control over the company's bank accounts after he and Trump adviser Alex Bruesewitz launched the firm in 2017. Starting in 2021, the complaint alleges, Utley began funneling company money into his personal life, splurging on sports cars, designer clothing, jewelry, and luxury condos.

In 2025 alone, Utley spent a whopping 200 days at the Seminole Hard Rock Hotel & Casino in Hollywood, Florida, dropping $29 million in company funds into slot machines, X Strategies alleges. Utley allegedly won back more than $26 million, but kept the winnings for himself while the company was left holding a $3 million loss. The filing further alleges Utley pulled cash from casino ATMs and told banks the withdrawals were for client entertainment.

The alleged shortfall came to light after the firm brought on Michael Seifert, the former CEO of PublicSq, a marketplace that connects conservative consumers with small businesses, as X Strategies' president. Utley departed from the social media company in April and gave up his 50% ownership stake.

The lawsuit brings civil RICO, theft, fraud and breach of fiduciary duty claims, and seeks damages that could be tripled.

"I dispute these allegations in the complaint and will address them through the legal process," Utley told POLITICO. "I have no further comment at this time."

Weisheimer, a social media influencer and Pilates instructor, also denied any wrongdoing.

"I have absolutely nothing to do with the drama between Alex and Derek. I briefly dated Derek, during which time I asked him to purchase a Pilates studio for me. He ultimately decided not to, and our relationship ended shortly thereafter," Weisheimer told The Independent. "I have requested that I be removed from this lawsuit immediately, as I have no involvement in the issues between these two gentlemen."

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