Brian CheungTrump's media stock will start trading Tuesday. Here's what to know.

Truth Social's parent company could give the former president a financial lifeline worth billions of dollars, but there are still some big questions.

Former President Donald Trump arrives at 40 Wall Street after his court hearing in New York on Monday.Charly Triballeau / AFP - Getty Images file
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Donald Trump's media company is set to make its debut on the stock market Tuesday, a development that could generate a windfall for the cash-strapped former president.

His stake in the firm — Trump Media and Technology Group, the parent company of Truth Social — is worth billions.

But that is wealth on paper, and a number of things would have to happen to allow him to cash out on that stake and address some of his financial issues, including the mounting legal bills in his criminal cases and a hefty appeal bond stemming from a civil fraud case in New York. An appeals court slashed that bond to $175 million Monday, down significantly from the original amount of $464 million.

Here are some of the big questions surrounding Trump Media's market debut:

How is Trump's company going public?

Shareholders in the shell company Digital World Acquisition Corp. (DWAC) agreed Friday to merge into Trump Media.

The newly combined company will trade on the Nasdaq exchange under the stock symbol DJT.

When was the last time a Trump company went public?

Trump's hotel and casino resort company, which focused on his Atlantic City gambling and entertainment venues, started trading in 1995 — also under the ticker DJT. The company ended up filing for bankruptcy in 2004.

Is Trump Media holding an initial public offering (IPO)?

No. 

DWAC was founded in 2021 as a special purpose acquisition company, or SPAC. This kind of firm raises money before deciding on a company to acquire, which is why they're also commonly referred to as a "blank check company."

DWAC hit the public markets, raised a bunch of money and then announced plans to acquire (or merge with) Trump Media and Technology Group, the formerly private firm that owns his social media platform, Truth Social.

That announcement happened in 2021, but faced delays from legal holdups and investigations, including fraud/insider trading charges from the Securities and Exchange Commission. In the case of the SEC, a settlement last year slapped the company with an $18 million penalty but paved the way forward for the merger.

How much does Trump stand to gain?

It’s hard to say. 

Trump would have almost 80 million shares in Trump Media, or about 58% of the company. As of DWAC’s opening share price Friday, that could value his stake at more than $3 billion.

DWAC shares, which fell Friday but then surged again Monday, have more than doubled this year but are still way off their 2022 high points. Its volatility provoked criticism that it's a "meme stock" driven by a fan following, rather than business or market fundamentals. Trump Media has lost millions while posting under $3.5 million in revenue during the first nine months of 2023, according to the most recent information available.

Can Trump sell his stock instantly?

No.

According to the merger agreement, he cannot sell his shares for six months, part of a “lockup” procedure standard in many merger deals.

But, there's a big caveat. The combined company’s new board of directors could vote to allow Trump to sell his shares earlier than that. And the board is set to include his son Donald Trump Jr., as well as Linda McMahon and Robert Lighthizer, who were members of his administration.

If Trump does get permission and, in turn, sells shares, it may open the company — and him — up to legal challenges from shareholders left holding the bag if a sale tanks the company's stock. Although most of the shareholders are likely Trump supporters, it could only take a few disgruntled shareholders to mount a legal challenge and allege that Trump did not act in the best interest of shareholders by cashing out.

Can Trump put up his shares for a loan?

There could be some financiers willing to take Trump’s shares as collateral for a massive loan that he could use to then cover the money he needs to post in order to appeal the decision in his New York civil fraud case. On Monday, a New York appeals court reduced the amount of the bond and said the former president has 10 days to deliver it.

However, there also may be legal challenges to getting a massive loan by pledging any DJT stock.

That's because the stockholder lockup agreement that currently prevents Trump from selling his shares within six months also states that he cannot: "lend, offer, pledge, hypothecate, encumber, donate, assign, sell, contract to sell, sell any option or contract to purchase, purchase any option or contract to sell, grant any option, right or warrant to purchase, or otherwise transfer or dispose of, directly or indirectly, any restricted securities."

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