Legal Fight Over Trump Media’s Ownership Adds to Its Woes

Twenty years ago, Wes Moss and Andy Litinsky met Donald J. Trump as contestants on his reality TV show, “The Apprentice” — a connection that led them to help launch the former president’s social media platform, Truth Social, with his blessing.

Now, they might as well be starring in an episode of “Family Feud.”

For weeks, Mr. Moss and Mr. Litinsky have been fighting with Trump Media & Technology Group, the parent company of Truth Social, over their roughly 8 percent stake in the company. In February, they sued the company, claiming that Trump Media — which made its trading debut last month at an $8 billion valuation — was trying to deprive them of the full value of their shares. Now they also claim the company is trying to prevent them from selling those shares.

In a separate lawsuit that followed, Trump Media claimed that Mr. Moss and Mr. Litinsky should forfeit their shares because their poor decision-making had contributed to a yearslong delay in its merger with Digital World Acquisition Corporation. Trump Media agreed to merge with Digital World, a cash-rich shell company, in 2021 as a way to go public, but the deal closed only in March.

The pair’s stake is worth more than $220 million based on the current $26 share price of Trump Media, compared with $2 billion for Mr. Trump. Overall, the stock has fallen about 62 percent from where it began trading on March 26.

The litigation provides a portrait of some of the chaos that has bedeviled Trump Media since its inception. The lawsuits are also a distraction for the fledgling company, which is struggling to show that it is a viable business rather than a money-losing entity whose value is derived solely from Mr. Trump’s presence on its flagship platform. On Tuesday, the company announced plans to launch a streaming video service to draw in more users.

Mr. Moss, now an Atlanta financial planner and radio host, and Mr. Litinsky, a conservative media personality, met Mr. Trump during the second season of “The Apprentice,” which ran for 15 episodes in 2004. Mr. Trump “fired” the two men in Weeks 11 and 12. Mr. Litinsky would later take a job as president of Mr. Trump’s television production company.