A leveraged bet at the top of a “buy-high” cycle tends to do one thing: deepen the downside. In 2025, Donald Trump’s family did just, wagering billions of dollars on bitcoin.

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........

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