Former President Donald Trump is on the verge of a multi-billion dollar windfall at a time when he’s facing immense financial and legal pressure.
Trump Media & Technology Group, the owner of Trump’s struggling social media platform Truth Social, is on the cusp of going public as soon as next week following years of legal and regulatory obstacles.
If shareholders vote on Friday to approve Trump Media’s merger with a blank-check company, Trump will own a dominant stake in a public company, with shares worth more than $3 billion at current market prices.
However, experts tell CNN there are numerous practical, financial and legal reasons why this deal – even if it gets approved – is unlikely to solve Trump’s imminent cash crunch.
“President Trump won’t be able to monetize that stake right away,” said Matthew Kennedy, senior initial public offering market strategist at Renaissance Capital.
Trump faces a Monday deadline to post a $464 million bond in New York’s civil fraud case against him or New York’s attorney general could try to seize his golf course and private estate north of Manhattan – or other assets.
The good news for Trump is that there are strong incentives for shareholders to approve the merger with Digital World Acquisition Corp.
If it gets the green light from shareholders, Trump stands to be the dominant shareholder, with a stake of at least 58.1%, according to filings.
The merger agreement calls for Trump to own roughly 79 million shares of the new public company – and potentially tens of millions more if certain goals are hit.
At Digital World’s current share price of around $43, that massive stake would be worth $3.4 billion – at least on paper.
The merger could close swiftly.
Regulatory filings indicate the companies expect to close the merger on the second business day after the shareholder vote is approved. That sets the stage for trading to begin under the new name and ticker symbol by Tuesday or Wednesday, although it could take longer, according to Kennedy.
The bad news is that this stake is not as liquid as it sounds. Those paper gains would be very difficult for Trump to translate to actual cash.
In fact, Trump’s shares in this company are in many ways even less liquid than his real estate holdings, according to Charles Whitehead, a law professor at Cornell Law School.
First, experts say the market is drastically overvaluing Trump Media based on the company’s fundamentals.
That means Trump would have a hard time dumping the stock or even pledging it as collateral.
“The stock price is clearly a bubble,” Yale law professor Jonathan Macey told CNN. “No rational investor would take the stock at face value, especially if they had to hold it for any length of time.”
SEC filings indicate Trump Media’s revenue amounted to just $1.1 million during the third quarter. The company posted a loss of $26 million that quarter.
Not only that, but Truth Social appears to be shrinking.
The number of Truth Social’s US monthly active users on iOS and Android is down 39% year-over-year, according to Similarweb data shared with CNN earlier this month. Truth Social remains much smaller than X (formerly Twitter), which is also shrinking but at a slower pace.
Jay Ritter, a finance professor at the University of Florida, said the current market price is hard, if not impossible, to justify.
“It is grossly overvalued,” said Ritter. “It qualifies as a meme stock for which the price is divorced from fundamental value…Meme stock investors are usually buying on the basis of the greater fool theory of investing: It is overvalued today, but I hope to make money selling it to an even greater fool tomorrow at an even higher price.”
But even in the unlikely event that Trump found a taker for those shares, experts say he is likely not allowed to sell or pledge that stock – at least not yet.
As is typical in a deal like this, certain shareholders are subject to a lock-up period that prevents insiders from immediately selling.
“No one wants to buy into a company where the largest shareholder – and really the face of the biggest product – is selling,” said Whitehead.
In this case, key shareholders of Trump Media, including its management team, have agreed not to sell their common stock for six months to maintain “important stability to the leadership and governance” of the company, according to SEC filings.
Not only does that lock-up agreement prevent these key shareholders from selling their stock for six months, it says they have agreed not to “lend, offer, pledge…encumber, donate” that stock during the period.
If the share price stays above $12 for a period of time, it’s possible that insiders can sell or pledge their stock 150 days after the deal closes.
Moreover, there are additional lock-up restrictions contained in an amended charter that experts say appear to include Trump. That lock-up also restricts certain shareholders from immediately selling after the deal closes.
“If his shares are covered by the charter’s lockup provisions then, absent an amendment to the charter, President Trump cannot pledge this stock. Full stop,” Whitehead said.
And amending the charter would be tricky – even for Trump and his outsized sway over the company. That’s the kind of thing that would have to be disclosed ahead of time because it would impact potential buyers of the stock.
“He can’t do this quietly. If President Trump today intends to amend the charter and they are not disclosing this intention, that’s a problem,” Whitehead said. “Presumably, they would need to take the position after the vote approving the merger that President Trump woke up and suddenly said, ‘Hey, let’s amend the charter.’”
Now even if Trump overcame these potentially insurmountable obstacles, there is no guarantee any bank would take this stock as collateral in a loan.
“If I’m a bank, I’m going to be troubled by the idea of a significant shareholder pledging his stake,” Whitehead said. “Any bank doing a proper credit analysis must be sensitive to the fact that this stock may very well tank if it turns out that President Trump is looking to sell down the position.”
