Tyler and Cameron Winklevoss just wrote two checks of over $5 million each to MAGA Inc., the super PAC backing Donald Trump, after liquidating Bitcoin to cover the sum. A Tuesday FEC filing confirmed the transfers, bringing the twins' total political investment in Trump's orbit well past the $12 million mark since 2024.
The timing is hard to miss. The donation landed roughly a month after the U.S. Commodity Futures Trading Commission asked a federal judge to vacate a $5 million penalty it had previously imposed on Gemini, the crypto exchange the twins founded in 2014. No formal link between the two events has been established, but observers in the industry noticed the sequence immediately.
A pattern going back to 2024
This isn't the first time the Winklevoss brothers have converted crypto into political cash. In 2024 they donated 30.94 Bitcoin, worth just over $2 million at the time, to Trump's presidential campaign, framing it as a way to "put an end to the Biden Administration's war on crypto." During that period, Gemini itself was among the exchanges hit by aggressive regulatory action. Since Trump returned to office, several of those enforcement cases have been dropped.
MAGA Inc. has pulled in more than $400 million heading into the November midterms, and the twins' contribution is one of the larger single crypto-sourced donations to enter the fund.
The Winklevoss brothers have been Bitcoin backers since the early days, and industry insiders have long assumed they hold among the largest personal BTC positions in the space. Tyler's public statements leave little ambiguity about where he stands: back in 2024 he called Trump "the pro-Bitcoin, pro-crypto, and pro-business choice" and said anyone who disagreed was "severely misinformed, delusional, or not telling the truth."
Meanwhile, Gemini has had a volatile few months on its own. In May, the company's shares surged more than 20% in after-hours trading after the twins announced a $100 million Bitcoin-funded investment in the firm alongside Q1 results showing 42% year-over-year revenue growth. Net losses narrowed to $109 million, though trading volumes had slipped from a year earlier, reflecting Bitcoin's pullback from its October peak. The stock had already shed more than 89% from its IPO high before the bounce, weighed down by layoffs, executive exits, and shareholder lawsuits. A CFTC derivatives license granted in April gave the company at least one concrete piece of regulatory progress to point to.
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