• Trump Media, the company majority-owned by former President Donald Trump, fell below $20 per share for the first time since the Truth Social maker started publicly trading.
• Trump's stake of DJT stock is still worth more than $2.2 billion — more than half of his on-paper net worth, according to Forbes.
• A lock-up agreement on Trump selling his stock is soon set to expire.

The monthslong Trump Media stock slide continued Wednesday, as shares of the company majority-owned by former President Donald Trump fell below $20 for the first time since the Truth Social maker went public more than five months ago.

The stock price of DJT touched a low of $19.38 per share around midday, marking a drop of more than 75% from its intraday high on March 26, the day the company debuted on the Nasdaq stock exchange.

Trump Media ended Wednesday's trading session down more than 4% at $20.10 per share.

Trump Media has also lost more than half its value since its recent surge on July 15, the first trading day after the Republican presidential nominee narrowly survived an assassination attempt at a campaign rally in Pennsylvania.

A Trump Media spokesperson did not immediately respond to CNBC's request for comment on the stock's latest dive.

Trump owns nearly 59% of Trump Media's stock. Even after losing much of its value, Trump's stake at Wednesday's stock price is still worth more than $2.2 billion — more than half of his on-paper net worth, according to Forbes.

Trump, and other company executives and insiders, are bound by lock-up agreements that have so far barred them from cashing in on their shares.

But the lock-ups are set to expire as soon as Sept. 20, at which point Trump may choose to start selling his shares.

Trump has given no indication that he plans to cash out once he is able to do so. But speculation has flared that he might, especially as Trump Media's latest earnings reports show it losing millions of dollars and generating little revenue.

If he does sell — or if he even appears likely to — investors could lose confidence in Trump Media, a situation the company's own regulatory filings have acknowledged.

Similar to other meme stocks, investing in Trump Media has come to be seen as a way for Trump's supporters to back him and bet on his chances of beating Democratic Vice President Kamala Harris in the presidential election.

But the company has noted that its fledgling social media platform, Truth Social, depends at least partly on Trump's enduring popularity and reputation. Trump, who holds the most popular Truth Social account, has recently started posting more on X, his former messaging app of choice, and TikTok.

The stock's recent slide has also coincided with Trump's shifting political and legal circumstances. Trump's odds of winning the election appear to have narrowed after President Joe Biden withdrew his reelection bid and endorsed Harris as his successor.

Trump Media also announced last month that it had entered into an agreement with investment firm Yorkville Advisors, which could enable the company to issue up to $2.5 billion in stock to Yorkville.

The deal would "guarantee access to additional capital, if necessary, to pursue big strategic opportunities as we look to build out our portfolio by acquiring assets and technologies in the Patriot economy," Trump Media CEO Devin Nunes said in a July 3 press release.

The company noted in a separate regulatory filing, "The sale and issuance of Shares to Yorkville will cause dilution to our existing shareholders, and the sale of Shares acquired by Yorkville, or the perception that such sales may occur, could cause the price of our Common Stock to fall."