Trump Social Media Firm Co-Founder Allegedly Gambled Away $29m of Company Cash at Hollywood Florida Casino

Submitted by Jagajeet Chiba on

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Jagajeet Chiba

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Trump Social Media Firm Co-Founder Allegedly Gambled Away $29m of Company Cash at Hollywood Florida Casino

OAKLAND PARK, Fla. (Gambling911.com) - Digital firm X Strategies is suing its co-founder Derek Utley for allegedly embezzling at least $5 million from the company.  Utley, who resigned from the company back in April before being fired, denies the allegations. 

The civil lawsuit claims Utley spent $3 million of the stolen funds on slot machines at a single casino in 2025.  The rest, they claim, was spent to support a lavish lifestyle. 

X Strategies manages prominent social media accounts for US President Donald Trump, including Team Trump and the Trump War Room.  X Strategies has no corporate connection to Truth Social, the preferred social media account utilized by the president. 

The casino in question was allegedly the Seminole Hard Rock Hotel & Casino in Hollywood, Florida. According to the lawsuit, Utley allegedly spent 200 days there during 2025 and wagered enormous amounts on slots:

About $29 million lost on slot machines
More than $26 million won
Net loss: roughly $3 million

The lawsuit itself was filed September 18 in federal court in South Florida and the Seminole Hard Rock Hotel & Casino has yet to comment on the matter. 

The suit also names Utley's ex-girlfriend Anna Weisheimer as a co-defendant for allegedly helping launder funds, though she strongly denied any wrongdoing. 

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

Neither X Strategies or The White House have commented on the matter as of Wednesday morning. 


  • Jagajeet Chiba, Gambling911.com 

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