A crypto-backed political group linked to Cameron and Tyler Winklevoss is finding out the hard way that taking donations in Bitcoin can be risky.
The group, called the Digital Freedom Fund, raised more than $22 million in the final months of 2025. A big part of that money came in Bitcoin, donated during the height of last year’s crypto bull market.
Instead of converting the Bitcoin to cash right away, the group decided to hold onto it. That decision turned out to be costly.
In August, the Winklevoss twins — who run the Gemini crypto exchange — transferred 188.45 Bitcoin to the fund. At the time, Bitcoin was trading around $114,000. By the end of the year, the price had fallen below $88,000, cutting nearly $5 million off the value of the donation. As of December 31, the fund was still holding the Bitcoin.
Back then, holding the crypto seemed like a smart move. Bitcoin was climbing fast, and optimism was high. Tyler Winklevoss even said the donation was meant to support the midterm elections, back Donald Trump, and help turn the U.S. into the “crypto capital of the world.”
But that momentum didn’t last.
Bitcoin peaked near $125,000 in early October, then reversed sharply. By Friday’s latest check, it was trading below $82,000.
Federal election rules don’t require political action committees to sell crypto donations right away, but most choose to do so to avoid exactly this kind of risk. In this case, the price swing wiped out millions.
The Digital Freedom Fund didn’t rely only on crypto. It also received $1 million in cash from Kraken, one of the largest U.S. crypto exchanges, and reported just over $723,000 in cash on hand at the end of the year.
The fund is part of a growing group of crypto-backed political organizations trying to blend digital assets with traditional campaign finance — a process that’s still full of uncertainty.
At the same time, political winds are shifting. Trump’s approval rating recently fell to 37%, and reports suggest growing frustration within his own party.
For now, the lesson is clear: in politics, just like in crypto, volatility cuts both ways.
