Bitcoin’s wild price swings have dealt an expensive blow to one of the most high-profile political spending vehicles in U.S. crypto politics.
A super-PAC bankrolled by billionaire twins Cameron and Tyler Winklevoss is discovering that fundraising in Bitcoin can backfire when markets turn. A hefty donation made at the height of last year’s bull run has shed millions in value, illustrating how digital-asset volatility can collide with the slow, regimented timelines of American electioneering.
The group, called the Digital Freedom Fund, was created by the Winklevoss brothers to funnel money into races and causes aligned with their vision of a crypto-friendly United States. According to federal disclosures, the super-PAC hauled in more than $22 million in just the final five months of 2025. A sizable slice of that haul arrived not in dollars, but in Bitcoin—an asset the PAC chose to sit on instead of immediately converting into cash. That strategic choice has now become a cautionary tale.
In August, the twins, who co-founded and operate the Gemini cryptocurrency exchange, transferred exactly 188.4547 BTC to the Digital Freedom Fund, filings with the Federal Election Commission show. At the time of the transfer, Bitcoin traded around $114,000 per coin, giving the donation a paper value well above $21 million.
From a fundraising perspective, it looked like a coup. The market was in full bull mode, Bitcoin was marching toward record highs, and political operatives could plausibly imagine even more upside by holding the asset through the campaign season. Instead, the opposite happened.
Bitcoin’s rally stalled after touching nearly $125,000 in early October. By the end of December, the price had slid below $88,000. That retreat translated into a loss of almost $5 million on the value of the Winklevoss donation alone by year-end. As of December 31, disclosures show the super-PAC still held the Bitcoin on its books, meaning the unrealized losses remained locked in rather than crystallized through a sale.
As of the most recent check on Friday referenced in the filings, Bitcoin had slipped further, trading under $82,000. For a committee that opted to treat BTC as a treasury asset rather than transient payment, each leg down cut into its political war chest and its capacity to spend on ads, organizing, and voter outreach.
The original logic for holding the coins looked more compelling in August. At that point, Bitcoin was emboldened by strong market sentiment, institutional inflows, and a broader risk-on environment. In a detailed post on X (formerly Twitter) around the time of the donation, Tyler Winklevoss framed the move as part ideological, part strategic: the contribution was meant to influence midterm races, shore up support for Donald Trump, and push the United States toward becoming “the crypto capital of the world.”
That rhetoric fit neatly with Trump’s own public pledge that the U.S. would lead the world in digital assets and Web3 innovation. Yet, in practice, Washington’s posture remains far from the laissez-faire “crypto capital” vision. The regulatory landscape is fragmented, enforcement actions have unnerved the industry, and even pro-crypto donors are discovering how hard it is to align blockchain-era finance with campaign-law realities.
Under current Federal Election Commission rules, super-PACs may accept contributions in cryptocurrency, and they are not obligated to liquidate those assets immediately. In theory, that flexibility allows committees to hold digital assets as speculative treasuries, mirroring how some corporations park excess cash in Bitcoin. In practice, most politically active groups that take crypto opt to convert it to dollars soon after receipt, precisely to avoid the kind of market risk now confronting the Digital Freedom Fund.
The Winklevoss-backed fund did not rely solely on crypto. Federal filings show it also received a $1 million cash contribution from Payward Inc., the company behind the Kraken exchange. Even so, the PAC reported just over $723,000 in cash on hand at the end of the year, underscoring how much of its financial firepower was tied up in volatile digital holdings rather than liquid U.S. currency.
The Digital Freedom Fund is one of several super-PACs with deep ties to the crypto sector, as the industry experiments with how to translate token wealth into political clout. These groups aim to shape regulation, influence who writes and enforces financial rules, and back candidates who promise a friendlier climate for trading platforms, stablecoins, and decentralized finance.
Yet the Winklevoss case highlights a structural mismatch between markets and politics. Campaigns, ad buys, and ground operations require predictable budgets. Bitcoin, by contrast, can gain or lose double-digit percentages in a matter of days. A donation worth tens of millions at the time it hits the wallet might be significantly more—or significantly less—by the time it is actually deployed in an election.
The episode also unfolds against a softening political backdrop for Trump himself. His approval rating slipped to 37% in the latest Pew survey, a worrying sign for an incumbent projecting strength and inevitability. Reports suggest a growing contingent of Republicans is weary of his administration, frustrated by constant turmoil and inconsistent policy follow-through, including on issues like digital assets where expectations were set sky-high.
For crypto donors, this raises uncomfortable questions. If the core bet is that a particular candidate or party will usher in a boom era for digital assets, what happens when that candidate’s political grip weakens? The combination of a sliding approval rating and sliding Bitcoin price magnifies the perceived risk: money tied to a volatile asset is being deployed in support of a volatile political brand.
From a broader strategic standpoint, the Digital Freedom Fund’s experience may force other crypto-rich donors to reassess how they structure contributions. One option is to treat Bitcoin purely as a funding source—sell into dollars at or near the moment of donation and let campaigns handle only fiat. Another is to hedge exposure, using derivatives or stablecoins to lock in the dollar value of contributions while preserving some alignment with the crypto ethos.
Campaign treasurers, for their part, may begin insisting on stricter internal policies: automatic conversion of crypto contributions above a certain threshold, diversification across assets, or caps on the percentage of the war chest that can be held in digital form. The goal would be to ensure that market turbulence does not suddenly crater the budget weeks before a key primary or general election.
There is also a narrative dimension. Crypto advocates often present Bitcoin as “digital gold” and a long-term store of value. That framing can clash with its role in campaign finance, where the time horizon is short and outcomes are binary: a campaign either has enough money to compete or it does not. Watching millions in potential ad spending evaporate because Bitcoin retraced from its highs weakens the argument that it is a dependable asset for short-term obligations.
Still, the story is not entirely one-sided. If Bitcoin were to rebound ahead of the next election cycle, the Digital Freedom Fund could theoretically regain or even exceed the value it lost. That prospect is precisely why some donors and committees are willing to accept interim pain: they view volatility as a feature of an asset that, over multiple cycles, trends upward. In that sense, the Winklevosses are treating their political giving much like their investments—high conviction, high risk, and highly exposed to market sentiment.
The real test will be whether this high-risk approach translates into policy outcomes. If crypto-backed super-PACs can help elect lawmakers who push for clear, balanced regulation, predictable tax treatment, and room for innovation, donors may decide the volatility is a worthwhile cost of doing business. If not—if hundreds of millions in token wealth are spent and the regulatory environment remains hostile or ambiguous—pressure will grow to rethink the strategy entirely.
For now, the Digital Freedom Fund stands as a vivid case study in what happens when the frontier world of digital assets collides with the slow-grinding machinery of U.S. politics. A single decision—to hold rather than sell 188.4547 BTC—turned a triumphant headline contribution into a painful reminder that in both markets and elections, timing is everything.