A Little-Known Way That Trump Could Raise Money to Pay His Legal Bills

The former president’s social media company is finally set to go public. He could borrow against the value of his stake in the company.

Shares of former President Donald J. Trump’s social media company could start trading on the stock market as early as Monday, immediately raising his net worth by around $3 billion — wealth that Mr. Trump may be able to tap to pay his mounting legal bills as he seeks a second presidential term.

Mr. Trump urgently needs to come up with cash by Monday to cover a $454 million penalty imposed by a New York judge, who found that he had fraudulently inflated the value of his real estate properties in dealings with banks. This week, he asked an appeals court to pause the judgment or accept a much smaller bond. Last year, one of his political action committees spent $50 million on legal bills.

The imminent public debut of Trump Media & Technology Group — the parent company of the Truth Social digital platform — could provide Mr. Trump a way to raise cash, but it won’t be straightforward.

Trump Media is going public by merging with a publicly traded shell company called Digital World Acquisition Corporation. Shareholders of Digital World are expected to approve the merger on Friday after years of delay caused by regulatory and criminal investigations that came close to derailing it.

Under the terms of the merger agreement, major shareholders of Trump Media are barred from selling their shares for six months. The so-called lockup provision, which typically applies to any company going public, is meant to limit the number of shares available for sale and trading, and to avoid the perception that early shareholders don’t have faith in the company’s future.

But because Mr. Trump holds enormous sway over the company with his stake of more than 60 percent, and because his brand is critical to Trump Media’s success, he could try to get around those provisions. Mr. Trump could ask the board of Digital World to waive his restrictions on selling shares before its planned merger with Trump Media goes to a vote.

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