Cameron and Tyler Winklevoss, the billionaire twin co-founders of crypto exchange Gemini, have made one of the largest political donations in Bitcoin to date, pledging their support for US President Donald Trump’s pro-crypto agenda.
In a post on X on Wednesday, Tyler Winklevoss said the brothers contributed more than 188 Bitcoin, worth roughly $21 million at the time, to the Digital Freedom Fund, a political action committee (PAC) created to advance policies favorable to digital assets. According to the twins, the donation is aimed at shaping the outcome of the 2026 midterm elections, where Republicans hope to expand their majority in Congress and reinforce Trump’s crypto-friendly legislative priorities.
Goals of the Donation
The Winklevosses said the Digital Freedom Fund will coordinate with other pro-crypto groups to promote issues such as market structure legislation and a de minimis tax exemption for Bitcoin and other crypto transactions, which would make small gains tax-free. The PAC is expected to serve as a hub for lobbying and election spending to ensure continued momentum for Trump’s blockchain agenda.
“The Digital Freedom Fund will work with similarly aligned pro-crypto groups and look to identify and support other issues… that will unleash the potential of these technologies, our industry, and America,” the twins wrote. “And our private position will always be the same as our public position on these matters.”
The $21 million contribution comes just over a year before voters head to the polls in November 2026. The timing highlights the high stakes: after losing the White House and control of both chambers of Congress in 2024, Democrats are aiming for a comeback, while Republicans see an opportunity to consolidate power and cement Trump’s influence over digital asset regulation.
Political Context
Records with the Federal Election Commission show the Digital Freedom Fund PAC was formally established on July 11, with Janna Rutland listed as treasurer. Rutland has been tied to several other PACs and was previously involved with a nonprofit linked to former Republican presidential candidate Vivek Ramaswamy.
This is not the first time the Gemini founders have put Bitcoin behind Trump. In 2024, they donated around $2 million in BTC to his presidential campaign. The symbolic nature of the new $21 million figure is hard to miss: Bitcoin’s maximum supply is capped at 21 million coins.
The twins also contributed $5 million to the Fairshake PAC, which spent over $130 million during the 2024 cycle backing pro-crypto congressional candidates and targeting lawmakers it labeled “anti-crypto.” Fairshake reported raising $141 million by mid-2025 for future races, signaling that industry-backed political money will remain a potent force heading into the next election.
Relationship with the Trump Administration
The Winklevoss brothers have cultivated close ties with the Trump White House. They attended inauguration events after his 2024 victory and later joined a March crypto summit at the White House. In July, Trump personally acknowledged their support at the signing ceremony for the Guiding and Establishing National Innovation for US Stablecoins (GENIUS) Act, a bipartisan bill seen as a landmark step in providing regulatory clarity for stablecoins.
The twins also reportedly deepened financial ties to Trump through an investment in American Bitcoin, a mining firm linked to the president’s family.
A Point of Tension
Despite their alignment, the brothers recently appeared to part ways with the administration on one key issue: the nomination of Brian Quintenz to chair the US Commodity Futures Trading Commission (CFTC). Although they initially signaled support for Quintenz, they later urged Trump to reconsider, reportedly prompting the White House to ask the Senate Agriculture Committee to delay the confirmation hearing. That move has drawn mixed reactions, as several blockchain and crypto advocacy groups voiced strong support for Quintenz in a letter released the same week.
Looking Ahead
The Winklevoss donation underscores how deeply intertwined crypto and US politics have become, with industry leaders betting big on securing regulatory clarity and favorable legislation through direct political spending. With the 2026 midterms looming, their $21 million Bitcoin play signals that crypto’s top players see the ballot box as a key battleground for the future of digital assets in America.
