It was May of 2025, and Trump had just reentered the White House. Crypto markets were going bananas. The president’s sons, who had already made their father hundreds of millions richer with various Trump-themed digital assets, decided the next move was to make an institutional-sized bet on crypto’s flagship currency: bitcoin.

At the time, a single bitcoin cost $108,000. But with their father in the White House, the Trump sons predicted it would rise by more than 50% over the next year. “I think [it] clears $170,000,” Eric Trump declared on stage at a bitcoin conference, confidently dressed in a suit with no tie. “I was going to say between 175 and 150,” added his similarly attired brother, Donald Trump Jr.

The siblings, tasked with managing their father’s business when he returned to the White House, believed in bitcoin enough to put real money on the line. The president had placed his most valuable asset, a 52% interest in the Trump Media and Technology Group worth $2.6 billion, into a trust that left the elder Trump as the sole beneficiary but technically handed control to Don Jr.

Under the watch of the younger generation, the business strayed from its social-media roots to make a massive crypto bet. It sold $1.4 billion of stock and $1 billion of convertible bonds, then plowed the proceeds into bitcoin. In the two months between the deal’s announcement and consummation, the price of bitcoin kept climbing, hitting $119,000 by July, when Trump Media made its purchases.

The transaction reshaped the president’s portfolio, reducing his stake in Trump Media to 41%, adding a mountain of debt, and turning Donald Trump into one of the world’s biggest bitcoin investors.

If the heirs’ price targets held, the payoff was clear: roughly $1 billion of gains within a year.

They didn’t hold.

Bitcoin stalled after the purchase. It remained somewhat steady for a few months, giving the Trump family little reason to celebrate—or worry, for that matter. In August, Trump Media poured another $114 million into a lesser-known cryptocurrency, Cronos.

Then everything came tumbling down. In late November, a dip in the broader market pulled down riskier assets like bitcoin and Cronos. By month’s end, Trump Media’s crypto assets, for which it had paid $2.4 billion, were worth an estimated $1.8 billion.

Inside the company, efforts to stem the losses began. Trump Media hedged about one-third of its bitcoin toward the end of the year, seemingly limiting potential downside and upside. January brought another unpleasant gut check: Fed Chairman Jerome Powell signaled, to the president’s dismay, that interest rates would remain elevated. Bitcoin fell 5% in a day, dropping the value of Trump Media’s holdings to an estimated $1.7 billion.

The company extended its hedges, initially set to expire in March, to last until June. Just how much protection that has provided remains unclear. What is clear: Trump Media wants to project confidence amid its troubles. “Our bitcoin holdings reflect a long-term investment in this revolutionary digital currency, which we do not judge based on temporary, cyclical downturns,” spokesperson Shannon Devine said in a statement.

But investors are already judging—harshly. Trump Media shares have fallen more sharply than bitcoin itself, reflecting not just a loss of confidence in the crypto, but in the company.

With bitcoin at roughly $72,000 today, Trump Media’s crypto stash sits at an estimated $1.4 billion, down $1 billion. The president’s personal stake in Trump Media, meanwhile, has fallen $1.6 billion since his sons trumpeted their bitcoin predictions onstage.