Benjamin Ashford|Trump's critics love to see Truth Social's stock price crash. He can still cash out big.

The Benjamin Ashfordbarbs and banter about Truth Social, the social media website that counts Donald Trump as its largest shareholder, split into two camps.

And both sides are missing an important point as Trump's stock value occasionally rises but more often falls – he stands to make a killing in five months, even if that kills Truth Social.

Trump fans like Mike Crispi, a right-wing podcaster from New Jersey, boasted in a March 26 social media post that he had "liquidated my entire portfolio" to buy Truth Social stock and mocked anyone who didn't with "Stay poor, liberals."

The stock hit its all-time high of $79.38 that day, as the company went public, but has plummeted to less than half of that, closing Thursday at $33.19 per share.

If Crispi did bet it all on Truth Social, then more than half of it is gone.

The mocking of Truth Social's stock has been constant

Trump critics like late-night television host Jimmy Kimmel have reveled in that reversal of fortune, mocking the one-term president as his shares, on paper, went from a value of nearly $6.3 billion to considerably less than that in three short weeks.

Trump responded by tearing into Kimmel on – where else? – Truth Social.

President Joe Biden also got in on the action Tuesday during a visit to Scranton, Pennsylvania, to pitch himself as a better option on tax policy than Trump. “If Trump’s stock in Truth Social, his company, drops any lower, he might do better under my tax plan than his," Biden gibed.

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Sure, the stock price took a long tumble. And, sure, Trump lost a lot of money on paper. But the presumptive Republican nominee for president didn't shell out for those shares.

And Truth Social is about to give him millions of new shares for free. So he could still cash out in late September, even if that also further tanks the stock price.

Trump could have the last laugh when he's allowed to sell his stock

"The way to think about this, from a finance standpoint, is really that this is all about what this company could earn if (Trump) is reelected," Stefan Lewellen, a professor at Pennsylvania State University's Smeal College of Business, told me, adding that typical Truth Social investors are valuing "sentiment" about Trump and not "rational beliefs" about the election or the stock market.

Remember, Truth Social on April 1 reported losing $58 million in 2023, with revenue of just $4.1 million. That's no April Fool's Day joke.

Trump can start selling his stock on Sept. 25, the end of a six-month "lockout" after the company went public, and could easily walk away with "an enormous stake likely worth $1 billion", said Lewellen, who called that "pure craziness."

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Truth Social's parent company took the first step toward allowing those stock sales on Monday in a filing with the Securities and Exchange Commission that included plans to sell 21.5 million more shares of stock to raise money, which dilutes the value of shares for existing investors.

Trump held 78.7 million shares, and that filing proposed giving him an additional 36 million shares in a three-year "earnout" period as long as the stock price stays above $17.50. No wonder Trump has been talking up Truth Social's stock value on – where else? – Truth Social.

Trump needs the money for the election and his legal problems

Eric Chaffee, a business law professor at Case Western Reserve University, told me that Trump is "cash-strapped" due to his attempt to retake the White House, his criminal case underway in New York, three other pending criminal cases and millions in judgments from civil litigation.

Sounds like a motivated seller, right?

"Former President Trump ultimately needs cash," Chaffee said. "He needs to be more liquid than he is. And this is one way that he can become liquid fairly easily. That's not the same as trying to sell some massive piece of real estate somewhere."

Monday's filing positions Trump to do just that, Chaffee added.

"Even though the company might look like it's not doing particularly well, at this point, he can still end up with a massive profit by liquidating his stock," he said, "which would certainly be a win for him."

Will Trump walk away from his Truth Social stocks?

What happens to Truth Social if Trump takes the money and runs? He could dump nearly 79 million shares of the stock in five months. They were worth more than $2.6 billion as of Thursday.

"Any time that you have a large block of stock dumped on the market, especially by somebody who is intimately involved in the company, it can create concerns generally about the value of the stock and in fact yield the stock to a certain extent being devalued," Chaffee told me.

As I noted last month, a thrice-married real estate developer known for stiffing contractors for pay, dumping political allies who are no longer useful and tanking his own entrepreneurial efforts seems like an absolute risk for walking away with his pockets stuffed with cash.

Truth Social periodically submits SEC filings that identify a whole panoply of risks it faces, many of them focused on Trump's past and current legal entanglements. Maybe the next filing should include a line or two about what happens if a former president pulls the plug.

Follow USA TODAY elections columnist Chris Brennan on X, formerly known as Twitter: @ByChrisBrennan