Set your timer, because in 27 days, “The Donald” gets his first shot at turning his social media fortune into an unbelievable amount of money. But whether he’ll dump his shares or not? That’s a mystery even Colter Shaw would struggle to crack.

(Source: IMDb)

Let’s not kid ourselves, $2.6 billion is a massive chunk of change. And for Trump, who’s currently staring down the barrel of more than half a billion dollars in legal bills, cashing out some of that social media fortune probably looks pretty tempting. 

With the lockup period set to expire around September 20, Trump could finally start liquidating some of those 114.75 million shares he’s sitting on. But—and this is a big “but”—things get complicated fast.

If Trump starts unloading his shares, it could will send a message louder than any “mean tweet.” He would 100% be signaling that he’s not as confident in Truth Social as he’d like everyone to believe. And let’s face it, for a guy who’s built his entire persona on unshakable confidence—remember when he hilariously called Rosie O’Donnell a pig on national TV?—that wouldn’t exactly be a strong move.

If you’ve been following along, Trump Media, with its Truth Social platform, isn’t exactly a hit among Wall Street analysts. And let’s be real—it’s not just because they’re probably not fans of the former president. 

If you take all the emotions and political biases out of it, the stock price has been all over the place since it went public via a SPAC merger in March, swinging from a high of $79.38 to a low of just under $22. And while the company is bleeding money faster than a leaky faucet (we’re talking a $344 million loss in just the first six months of the year), Trump’s potential cashout could have some serious repercussions.

If Trump starts selling, it could tank the stock price, leaving investors to wonder if the pilot is jumping out of the airplane mid flight, parachute and all. But holding on might reassure his loyal followers that he’s still all in.

There’s also the political angle to consider. The former President didn’t just create his social media company as a business opportunity; it’s a crucial part of his political strategy. With the next election set for November 5, 2024, if Trump decides to sell, it could appear as though he’s cashing in on his loyal followers’ trust. You don’t need to be a Harvard graduate to realize this won’t help his chances of winning the election.

But let’s be real—Trump is a businessman at heart, and a businessman knows when it’s time to take profits. In the end, it’s a question of money versus message—whether he sells or holds. After all, $2.6 billion can cover a lot of legal bills, and maybe even fund a few more golf courses. But, whether Trump decides to sell or hold, one thing is certain: I’ll be watching closely come September 20. If you have a stake in Truth Social, this is a date you won’t want to miss.

Stock.News does not have positions in companies mentioned.