Trump is about to get the all-clear to cash in on media shares

(Bloomberg) — Donald Trump is a month away from being able to turn his paper social-media fortune into cold, hard cash. The question is, will he?

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The former president will be able to start selling bits and pieces of his $2.6 billion ownership in Trump Media & Technology Group Corp. (DJTWW, DJT), whose share price has fluctuated wildly since going public through a special-purpose acquisition company merger in March.

Trump has not indicated any intention to sell shares in Trump Media, which operates his social-media platform Truth Social. And, doing so could give the impression that Trump is prioritizing personal profits — a criticism pundits often level at him — and alienate loyal followers who poured money into the company’s stock as his presidential campaign surged earlier this year.

However, the Republican nominee is also facing massive legal bills that a sale could help cover.

“It’s complex,” said Michael Ohlrogge, an associate professor at New York University Law School who has researched SPACs. Trump would need to balance the potential profits against any longer-term goals like a return to the White House, he said.

Representatives for Trump Media did not reply to requests for comment. They previously said that reporting on Donald Trump’s path to cashing out of the firm would be “utterly baseless” and partisan, “without any conceivable sign anywhere that he plans to do so.”

Trump, who owns about 60% of Trump Media, is expected to be able to start selling shares as soon as Sept. 20, when a lockup period barring insiders from selling shares is lifted. So will his co-founders, Andy Litinsky and Wes Moss, both former contestants on The Apprentice, as well as Patrick Orlando, whose fund, ARC Global Investments II LLC, sponsored the SPAC that merged with Trump Media.

Since that deal closed on March 25, the company’s shares have fluctuated drastically, trading as high as $79.38 and as low as $22.18. They closed at a fresh low of $22.24 on Monday, giving Trump Media a $4.3 billion market capitalization.

Trump selling a large number of shares could “be perceived as sending a signal about his lack of confidence in the company,” Ohlrogge said. “This could look bad in its own right, and a drop in share price could look bad for him as well.”

The volatility seems to have little to do with the underlying business, which is losing money as third-party trackers show stagnant user metrics. The company lost $344 million in the first six months of the year, mainly because of paper losses on derivatives, and took in just $1.6 million in sales.

Instead, Trump Media has become a way for investors to bet on Trump’s potential return to the White House. Its sharp swings have been mostly driven by retail-trading frenzies fueled on Reddit’s WallStreetBets and StockTwits — which can evaporate just as quickly as they start.

The stock’s latest slide has coincided with a drop in the implied probability that Trump will win in November, according to PredictIt. The betting market shows his odds have slipped to 46% from 69% last month, as Vice President Kamala Harris, the new Democratic nominee for president, has gathered support. The Democratic National Convention is underway in Chicago this week, with officials and celebrities rallying around her.

Whatever the rationale for Trump Media’s valuation, selling shares would help its namesake founder pay for mounting legal bills.

Trump is on the hook for more than half a billion dollars in penalties after losing a pair of lawsuits earlier this year, both of which he has appealed. He also faces an ongoing prosecution over his attempt to overturn the result of the 2020 presidential election he lost to Joe Biden.

The lockup period will likely end just a few days after Trump’s sentencing in his hush money criminal trial, set for Sept. 18 in Manhattan. Trump faces as long as four years behind bars on felony counts of falsifying business records to conceal a payment to a porn star before the 2016 election to keep her quiet about an alleged affair.

The exact day the former president and other insiders will be able to sell depends on the stock price. If shares remain at or above $12 for any 20 trading days starting Aug. 22 then the earliest trading day for insiders to sell shares will commence as soon as Sept. 20. If the stock fails to hold that mark, insiders will be able to sell shares by Sept. 26 regardless of how it’s trading.

“If he goes in and starts selling, that will hammer the stock price,” said Tuttle Capital Management chief executive officer Matthew Tuttle. “It’s going to depend on whether he needs the money.”

—With assistance from Erik Larson, Jef Feeley, Hadriana Lowenkron and Matt Turner.

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