Donald Trump has built his entire brand around being a winner. But on January 20, 2021, he looked the exact opposite. On every front.
Defeated by voters and facing his second impeachment after the Capitol riot he fomented, Trump returned to Palm Beach, Florida, to an empire in crisis. His commercial properties were largely vacant, his hotel business was losing tens of millions, and his licensing efforts were stalled.
A week later, Trump hosted Wes Moss and Andy Litinsky, former contestants on the American TV show “ The Apprentice ,” at his private club for a business proposal for something that piqued the master’s interest: a Trump-branded media and technology company, including a Twitter-like social media app, a Disney+-like streaming service and a website hosting platform like Amazon.
The most appealing part of the proposal? Trump would get a 90 percent stake — and, according to a person involved in the deal, he wouldn’t have to put up a dime up front.
Thus began a four-year transformation that has seen America’s most famous real estate billionaire become the first American to make billions from his political career. Other wealthy people have run for office, and many politicians — including every living former president — have leveraged their fame and connections to enrich themselves after their careers. But no one has made as much money, or on the scale, as Trump.
Billion dollar portfolio
In early 2021, Forbes estimated that Trump was worth $2.4 billion, with $1.4 billion tied up in traditional commercial properties and $1 billion of that concentrated in New York City.
Now he returns to the Forbes 400 list with an estimated net worth of $4.3 billion, most of it — $2.2 billion — from his social media business, which went public in March. The figures are as of Aug. 30, when we finalized the figures for the list.
Just $600 million is now in commercial real estate in New York. In less than four years, he has completely increased and transformed the fortune he built over 40 years.
Presidential inheritance
The presidency has certainly boosted Trump’s profits at his core businesses, helping to boost his operating income to an estimated $218 million last year, 58 percent more than he typically made while in the White House, according to an analysis of tax returns, financial disclosures, securities filings and internal documents.
Once a minor part of his empire, his golf clubs and courses have become a cash cow, a literal way to sell access to the world’s most famous man in the form of sky-high membership fees. Forbes estimates that this segment of his wealth is now worth $1.1 billion, up from $570 million when he stepped down, with profits tripling.
Also contributing to his income is a random assortment of internet-driven products, ranging from coffee table books to NFTs, Bibles and even pieces of the suit he wore to the debate against Joe Biden in June of this year. What is Trump really selling? Himself.
He’s been doing this for decades, ever since he was a 30-something living the high life in Trump Tower; through the ups and downs, one thing has remained constant: He’s earned the trust of people who don’t scrutinize him too closely, and then he’s cashed in.
Trump-mania
When Trump fails, he doesn’t give up — he simply finds a new proposition and, often, a new audience. In politics, he has developed a huge following, more passionate and loyal than any of his previous clients, eagerly buying whatever the former president offers at whatever price he decides to sell it.
All of this converges, on an unprecedented scale, at Trump Media & Technology Group, the parent company of Truth Social, a copy of Twitter.
From a financial standpoint, it is a failed business. The company generated just $3.4 million in sales in the 12 months through June and posted a net loss of $380 million.
Revenue has fallen nearly 10% in the past year, even as majority owner Trump dominates most of the news. The company lacks a clear business plan, especially now that Elon Musk owns X (formerly Twitter), eliminating the need for a right-wing alternative.
Nor does it have inspiring leadership — CEO Devin Nunes, who previously worked in agriculture and government, sold about a quarter of his shares in August to cover tax payments. Even so, Trump-friendly investors still valued the company at $3.8 billion late last month. If someone other than Trump were running the company, investors would likely value it closer to zero.
Trump Media & Technology Group did not respond to questions for this story.
Just as Trump has changed politics, he has also changed politics, rewriting the rules for how to profit financially from the presidency. Only one person saw it coming. “It’s very possible,” the 45th president predicted in an interview with Fortune 24 years ago, “that I could be the first presidential candidate to run and profit from it.”
The fall of Trump Tower
Linking Trump Tower to politics has come at a cost. By transforming a brand known for luxury into one defined by ideological division, operating profits have fallen from an estimated $184 million in 2015 to $141 million in 2017.
Product licensing partners fled, cutting off deals that put his name on ties, mattresses and shirts. That cost the candidate about $3 million a year. Hotel customers also stopped coming, sending profits at his Chicago location down 74 percent. Just as his income was drying up, his political spending was rising, eroding his cash flow.
He spent $66 million on his 2016 campaign, won the election, and days later agreed to spend another $25 million to settle a fraud lawsuit involving Trump University. When he moved into the Oval Office, his balance sheet was just $76 million in cash, less than half the $192 million he reported at the start of the campaign.
Power did little to help Trump’s finances—at least initially. He certainly tried to monetize the presidency, notably turning Mar-a-Lago into a “winter White House.” In an attempt to funnel millions of campaign dollars into his businesses, he offered to host the G7 conference at his golf resort, among other things. But none of that made up for the damage the policy did to Trump’s brand.
There was no ignoring the problems when the pandemic hit. Trump’s estimated operating profit fell to a low of $110 million. His five hotels reported an estimated loss of $23 million. More troubling: His commercial properties, where long-term tenants had remained amid the political turmoil, began to show signs of distress. The Trump Organization renegotiated its lease with Gucci, Trump Tower’s main tenant, cutting about $7 million off the rent. Occupancy fell to 75 percent from 89 percent as the building neared insolvency.
When Trump left office, he was worth about $2.4 billion, down from $4.5 billion on the day he announced his 2016 campaign in the lobby of Trump Tower. Eight months after the end of his presidency, Trump officially dropped off the Forbes 400 list for the first time in 25 years.
Reconquest of the billions
On October 20, 2021, about two weeks after falling off the Forbes 400 , Trump again hosted his apprentices at Mar-a-Lago. The club has stood out as a bright spot during his presidency as it has become increasingly intertwined with politics.
Some longtime members were unhappy with the change and decided to leave, which actually benefited Trump. The more people who dropped their memberships, the more newcomers he could bring in, charging ever higher membership fees. Freed from the White House, Trump centered his world at Mar-a-Lago and invited those who could write checks, rumored to be as high as $1 million, to join the extravaganza.
Its earnings report showed a jump in membership fees from $3 million in 2020 to $11 million in 2021. Similar trends were seen at its collection of golf courses, which had previously been a minor player in its portfolio but got a boost from the pandemic and is suddenly generating more than $40 million in annual operating profit, up from $17 million in 2020.
Truth Social
Despite all the new money, he still wasn’t eager to invest much in his media startup. That left the former “Apprentice ” contestants looking for other investors. By late October, they had raised more than $6 million with the help of Roy Bailey, a longtime business associate of Rudy Giuliani, and Kenny Troutt, the Dallas-based multi-level marketing billionaire, according to documents obtained by Forbes .
Then, in October 2021, the apprentices returned to Mar-a-Lago with a guest, a wide-eyed financier named Patrick Orlando, who was prepared to hand over nearly $300 million he had accumulated in a special purpose acquisition company , or SPAC.
Under giant chandeliers, Trump and Orlando signed documents to set up a SPAC deal that would merge Orlando’s public money with Trump’s private company, setting up Trump Media & Technology Group to go public even though it had virtually no operating company. They were essentially just taking Trump public.
They signed the papers, issued a press release and waited for the market to react. When the bell rang the next day, the SPAC’s shares soared on the prospect of a merger, jumping from $10 to $175, suggesting a post-merger valuation of about $30 billion. Orlando set to work raising another $1 billion from institutional investors.
The merger became embroiled in a web of investigations. Orlando’s own SPAC fired him, then the Securities and Exchange Commission (SEC) filed fraud charges. A business partner named Eric Swider took over, with considerably smaller ambitions. Eventually, the SPAC resolved its own problems with the SEC, moving forward with the merger while paying an $18 million fine. The stock rose 59% in less than a day, increasing the value of Trump’s stake to $6.3 billion and taking his total wealth to $8.1 billion, the largest ever.
Since then, the stock — and thus Trump’s net worth — has fluctuated wildly, often falling as the realities of the business have set in. At this point, the stock price is so disconnected from the company’s underlying financial fundamentals that the performance of Trump Media & Technology Group is almost irrelevant. He seems to know that his social media business is overvalued. Before the company went public, he himself said in his financial disclosure report that the company was worth at most $25 million.
Trump currently has about $413 million in liquid assets on his balance sheet after selling a Washington, D.C., hotel and a New York golf course. But a New York judge, who found the billionaire oversold his assets by acquiring both properties, has ruled that he must disgorge the proceeds from both deals, charging him $566 million in legal liabilities. The former president is appealing multiple lawsuits.
In the meantime, he’s doing what he can to help the stock price. Selling the stock would be a deceptive move, but it could also be one that could allow Trump to secure the first billion-dollar political profit in U.S. history, potentially securing his long-term place on the Forbes 400 list , a list he’s been a fixture of since its first edition in 1982. “Man is the most cruel of all animals,” he was quoted as saying in the inaugural edition, “and life is a series of battles ending in victory or defeat.”
