Newly public companies often implement lockup agreements to show investors that their top executives and financiers are committed and won’t race to cash out. But Trump’s lockup has proven unusually costly, at least on paper, given the size of his stake and the extent of the drop. Trump Media’s market debut in March propelled Trump into the rankings of the world’s 500 richest people. By last week, according to Forbes, he had slipped to no. 851. (Trump has previously said the Forbes ranking underestimates his fortune.)

Trump’s lockup period is expected to end around September 20, based on calculations established in financial filings and tied to the stock’s performance. Other executives and early investors in the company granted millions of dollars’ worth of salaries and stock will also be released from the lockup and be allowed to sell some or all of their shares around the same time.

But a selloff of shares among the company’s leadership could undermine the stock, driving new investors away. Trump Media has called Trump’s possible selling of shares one of many “risk factors” in securities filings and said the company would be “materially adversely affected” if he chose to divest his interest after the lockup period ends.

“You don’t want to be left holding a bag of possibility that once was overflowing,” Rekenthaler said. “But if you rush the process, that pushes down the stock price. It also doesn’t look good to shareholders, or generally to your belief in the company and its prospects.”

Trump’s shares in the company represent one of his biggest economic assets and could provide a major infusion of cash as he and his campaign are facing financial strain. Trump has been ordered to pay at least $US454 million in a civil fraud case in New York and $US83 million in a defamation case brought by the writer E. Jean Carroll. Trump, who is appealing both judgments, listed both liabilities as still in excess of $US50 million in a financial disclosure last month.

‘There’s no conceivable upside from the business aspect. … This is a personality stock and a celebrity stock.’

John Rekenthaler, a vice president for research at the financial services firm Morningstar.

Trump received 78.7 million shares when the company went public in March and an additional 36 million shares through an “earnout” provision one month later tied to the stock’s performance, securities filings show. If he had been able to sell all the shares at market prices immediately upon receiving them, his proceeds would have totalled more than $US6 billion, a trading analysis shows.

Trump Media’s stock price has roughly paralleled Trump’s performance in presidential election polls. Both surged after the assassination attempt but have declined in the weeks since President Joe Biden withdrew from the race and Vice President Kamala Harris began overtaking Trump in national polls. The company has warned in filings that its value could “diminish if [Trump’s popularity] were to suffer.”

Though Trump has continued to use Truth Social as his main online megaphone, he has in recent months also expanded his internet footprint to include other larger platforms that could erode a significant selling point: access to Trump.

His campaign now routinely posts videos of him on TikTok, where he has millions more followers. He has also resumed frequently posting to X, formerly Twitter, and last month sat for an exclusive interview there with its billionaire owner Elon Musk. Trump Media shares have lost about a third of their value since that interview.

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Trump Media shares are currently selling at the same price that its merger partner, Digital World Acquisition, was trading for at the beginning of the year, when the merger deal was in doubt. When Digital World announced the merger deal in October 2021, some investors bought shares for as much as $US175.

Trump Media has said its stock is owned by hundreds of thousands of retail shareholders, many of whom are amateur investors who support Trump and have seen its falling price as a test of faith.

Chad Nedohin, a longtime Trump Media supporter in Canada who posts video blogs about the company on the streaming site Rumble, wrote on Truth Social that the stock price was “a hoax to get people to sell.”