A super-PAC backed by crypto billionaires Cameron and Tyler Winklevoss is learning the hard way that political fundraising in Bitcoin can be a risky bet. A large cryptocurrency donation made during last year’s bull market has since lost millions in value, Bloomberg reported. The plummet underscores how volatility can complicate both campaign finance strategies and promises. After all, President Trump pledged that the U.S. would be a “crypto capital” — today, it’s anything but. Summary Winklevoss-backed super-PAC, Digital Freedom Fund, raised over $22 million in late 2025, including a major Bitcoin donation. Holding 188.4547 Bitcoin instead of converting it to cash caused a $5 million loss as the cryptocurrency fell from ~$114,000 to under $88,000. The super-PAC continues to hold crypto while also receiving $1 million in cash from Kraken, highlighting the risks and challenges of using digital assets in political fundraising. The Digital Freedom Fund, a political fundraising group launched by the Winklevoss twins, raised more than $22 million in the final five months of 2025, according to federal filings. A significant portion of that came in the form of Bitcoin (BTC), which the super-PAC chose to hold rather than immediately convert to cash—a decision that proved costly as prices fell sharply. In August, the twins, who run the crypto exchange Gemini, transferred 188.4547 Bitcoin to the Digital Freedom Fund, filings with the Federal Election Commission show. At the time, Bitcoin was trading at roughly $114,000. By the end of the year, however, the price had dropped to under $88,000, reducing the value of the contribution by nearly $5 million. As of Dec. 31, the super-PAC was still holding the digital asset. Holding onto Bitcoin may have seemed prudent when the donation was made, as the cryptocurrency was riding a strong bull run. In a lengthy post on X at the time, Tyler Winklevoss said the contribution was aimed at influencing midterm elections, backing Trump, and helping make the U.S. “the crypto capital of the world.” But Bitcoin’s momentum reversed after peaking near $125,000 in early October. As of Friday’s last check, it was trading below $82,000. Source: CoinGecko Federal rules do not require super-PACs to immediately liquidate cryptocurrency donations, though most convert them to cash relatively quickly. In addition to crypto, Digital Freedom Fund also received $1 million in cash from Payward Inc., operator of the Kraken exchange, and reported just over $723,000 in cash on hand at year’s end. The fund is one of several crypto-backed super-PACs active in U.S. politics, as the industry continues to test how digital assets fit into traditional campaign finance. Meanwhile, Trump’s approval rating dropped to 37% in the latest Pew poll, and a growing number of Republicans are reportedly fed up with his administration.
