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

Submitted by Jagajeet Chiba on

Written by :

Jagajeet Chiba

Published on :

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 

Related Content

Arkansas Saracen Casino Dirty Laundry Exposed as Two Execs on Hot Seat

Arkansas Saracen Casino Executive Hospitalized After Being Told He Will Be Terminated

Both men accused of developing gaming software marketed to “third parties within the Arkansas gaming industry.” Chief Market Officer denies allegations.
Seminole Classic Casino Hollywood Florida October 2026 Promotions Includes Reduced Baccarat Commission

Seminole Classic Casino Hollywood Florida October 2026 Promotions Includes Reduced Baccarat Commission

The casino will also feature a Baccarat tournament every Friday of during the month of October as well as a Blackjack tournament and Bingo special event.
ClubWPT Gold Shuts Down in Nevada

ClubWPT Gold Shuts Down in Nevada

The announcement coincided with news that all purchases on the site will cease immediately, postal requests will no longer be accepted and sweepstakes game play will no longer be available effective this coming Monday September 28, 2026.
New York Governor, AG File Lawsuit Against Polymarket

New York Governor, AG File Lawsuit Against Polymarket

Polymarket Chief Legal Officer Neal Kumar called the lawsuit a "media hit" against the company, and said it was open to working with the state rather than fighting in the courts.