The Financial Tightrope: Donald Trump's $464 Million Challenge

In the next few days, Donald Trump attempted to pull off an extremely delicate financial tightrope.

Long story short: Donald needs to come up with $464 million by MONDAY. Donald Trump does not have $464 million. He does own a bunch of valuable real estate. Unfortunately, NY State does not accept partial real estate assets to pay civil penalties. Donald has not been able to convince a third party to pay the debt on his behalf using his real estate assets as collateral. Typically, that would leave just one option: A real estate asset fire sale that Mr. Trump would really, really, really prefer to avoid.

And because you can apparently never count Trump out, there is an insane twist to this story: If a shareholder vote on FRIDAY goes his way, Donald will instantly own roughly $3 billion worth of equity in the public company that will merge to own his social media platform, Truth Social. But even a successful vote on Friday does not mean this financial tightrope walk is over…

How Did We Get Here?

Well, back in 2009, Hillary and Bill Clinton registered the domain name clintonemail.com. Over the next six years, Hillary sent thousands of personal AND government emails through this private email server instead of her secure @state.gov server. For example, on November 27, 2012, someone sent [email protected] a link to a CelebrityNetWorth article titled "The Richest People Of All Time – Inflation Adjusted," with the message: "Here's the article I told you I would send you and the President! Enjoy!"

Hillary forwarded the email to an aide named Robert Russo, [email protected], with the message:

"Pls print."

This really happened. Here’s a link to the archived email on Wikileaks.

Fast forward a few years… Hillary, after drastically overestimating her overall political appeal and rigging the Democratic primary to make herself the party's candidate over Bernie Sanders, fainting at a 9/11 memorial service, pretending to carry hot sauce in her purse at all times, and deciding to not visit Wisconsin ONCE during her campaign… loses the Presidency to Donald Trump. Yada yada yada… it was a wild four years that culminated in a pandemic and a bunch of riots, which ultimately resulted in Donald getting banned from his favorite form of communication, Twitter. In reaction, Donald started his own version of Twitter, called Truth Social.

The Financial Crisis

Now, let’s jump to last month. Last month, Donald Trump was ordered to pay New York State a $454 million civil penalty after he was convicted of defrauding banks by falsely inflating his net worth to obtain bank loans. It was an objectively stupid case that I bet even a staunch liberal would admit felt clearly politically motivated. With interest, the debt has now risen to $464 million. As we stated previously, Donald Trump does not have $464 million in cash, he hasn’t been able to attract a third party to put the money up on his behalf, and he would really prefer to avoid a real estate fire sale.

Thankfully, Donald is by far the largest shareholder in a company called Trump Media & Technology Group (TMTG), whose primary asset is Donald's Twitter knockoff, Truth Social. In October 2021, TMTG announced it was planning to go public by SPAC merger with a company called Digital World Acquisition Corp (DWAC). Two and a half years after that announcement, the TMTG+DWAC+SPAC merger IPO is about to become real… depending on a vote this Friday.

The Shareholder Vote

On Friday, March 22, DWAC shareholders will finally vote on whether they want the company to merge with Trump Media. They do. The only reason this company exists is to merge with Trump Media. So, if the majority of DWAC shareholders vote YES, Donald will instantly own 78,750,000 shares of the publicly traded DWAC. DWAC's share price closed at $36.42 on Tuesday (as I’m writing this article). At that price per share, Donald's roughly 79 million shares would be worth…

$2.868 billion

Obviously, that’s enough to pay his civil fraud debt more than six times over. Unfortunately for Donald, it’s not that easy. NY State does not accept equity in companies, even those that are publicly listed, to cover civil fraud penalties. They accept cash. Further complicating matters is the fact that the covenants of the potential DWAC SPAC merger restrict Donald from selling OR LENDING his shares for six months. However, that’s just a rule set by DWAC, which could easily be removed. And since it would be very bad if DWAC removed that rule and Donald suddenly dumped a billion dollars (pre-tax) worth of shares on the open market, it’s more likely that a rule change would result in Donald trying to find a third party to loan him $464 million using his shares as collateral.

Risks and Opportunities

Shares in a publicly-listed company are significantly less risky to lend against than Trump’s real estate assets. The only risk is the value of the shares used as collateral goes down during the six-month lockup. If that happened, Donald would likely have to kick in more shares to cover the difference.

But if it all worked out… After six months, Donald could cash out enough shares to pay off his loan. Or… maybe the third party would ask to keep the shares because they believe they’ll increase in value… especially if Donald is elected President again in November, which would be just two months after the six-month lock-up expires. For what it’s worth, shares of DWAC traded at $90 back in March 2022.

Oh! There’s a bonus. According to its SEC filing, if DWAC maintains a share price above $17.50 "for any 20 trading days within a 30-day trading period," Donald will be given 40 million additional shares. At $17.5 per share, that would be a $700 million bonus that could go towards paying down any loans.

The Potential Risks

Either way, a third party could easily charge Trump a 10-20% fee today in exchange for putting up the $464 million before Monday. If you had $464 million and were willing to roll the dice, you’d be looking at a $50-90 million payday for not a lot of work while doing a solid for a guy who has a 50/50 chance of being President again. Would you take that chance?

If DWAC shareholders vote NO on Friday, we’ll likely see a Trump real estate fire sale over the weekend. So that is the delicate financial tightrope that Donald needs to walk over the next few days.