Winning elections the Winklevoss Way

The twins’ new PAC is the latest example of a growing political brand. 08/27/2025

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You Can Go Your Own Way

A week ago today, Gemini co-founders Cameron and Tyler Winklevoss announced their creation of the Digital Freedom Fund PAC, seeding it with a $21 million donation in bitcoin. The announcement came as a surprise to much of the crypto industry not only because it was a secret in the preceding weeks, but also by contrast with nonpartisan crypto super PAC Fairshake, to which they had previously given millions.

“If Republicans lose either the House or Senate in the midterms on November 3, 2026 (only 1 year and 2 months away), then Democrats will have power to slow down and interfere with President Trump’s agenda,” wrote Tyler Winklevoss on the launch. “We don’t want that.”

The Digital Freedom Fund PAC is only the latest in a series of signals from the Winklevoss twins that their power and influence will turn towards narrower political priorities this cycle than the last. The vision they describe, in X posts, media interviews, and, according to sources present, in White House meetings, is one in which MAGA and crypto merge: where uncompromising conservatism blocks liberal sabotage, populism breeds price-boosting enthusiasm, and a unified central government responsive to the executive accelerates change.

Partisan advocacy is inherently a gamble. In a democracy, power eventually changes hands, and industries which align too closely with one party risk becoming a political football. But the twins are betting that the victories possible while Republicans retain power will outweigh the reprisals of an embittered Democratic party when the tides inevitably shift.

A press representative for Cameron and Tyler Winklevoss did not respond to multiple requests for comment.

Pro-MAGA, Anti-Everything Else

To understand the twins’ new strategy, one needs to first understand the dominant forces in crypto lobbying that they oppose.

In the last cycle, it is widely understood that three firms — Ripple, a16z, and Coinbase — dominated both public advocacy and money spent. They did this through massive donations to the PAC Fairshake, but also by backing the grassroots advocacy group Stand With Crypto and through their own lobbying. Their strategy has framed crypto politics as a single-issue, divorced from traditional partisan divides. Democrat or Republican, you’re either pro-crypto or anti-crypto, and thus the industry’s friend or enemy, accordingly.

The Winklevoss twins, meanwhile, frame crypto issues very differently. They describe the debanking of crypto companies as part of a broader story of political insiders weaponizing the federal government against their enemies — a story in which “lawfare” against the President was also a part. Progressive antipathy towards crypto, they say, is rooted in a leftist inclination to strangle American prosperity. Liberal San Francisco is “enemy territory,” and the Bay Area’s conservative tech leaders are taking down that enemy from the inside.

It is not entirely clear what triggered the Winklevosses’ defection, but it’s worth pointing out that they’re not alone. Many in the crypto policy world have actively worried that the forces within the Democratic party that oppose crypto, or view anticrypto sentiment as a convenient wedge, will force their sympathetic colleagues to betray their benefactors in the industry. The Winklevoss twins are far from the only crypto entrepreneurs who feel the industry is wasting its time supporting Democrats. Indeed, in April, Ben Smith reportedon a Signal group where MAGA ideology percolates among tech elites, identifying Tyler Winklevoss as a member.

But the fighting is not just about politics. In its adolescence, crypto in Washington is consumed by internecine bickering that is as much about power as any particular policy. The dominance of Ripple, a16z, and Coinbase, has increasingly frustrated others who feel sidelined, especially when their maneuvers are perceived to be missteps.

In one famous example, Ripple reportedly lost favor with the President after one of their lobbyists drafted a Truth Social post for his account which asserted that XRP would be in a national crypto reserve and startled much of the industry and the president’s own advisors. Coinbase and a16z have lost some influence with the White House as well after advocating for policies that put industry divisions on display. It is not just the Winklevoss twins that smell blood.

And the divisions run deeper than tactics. The so-called “market structure” legislation has become an increasingly salient policy divide within the industry. a16z, Coinbase, and Ripple’s preferred framework, the CLARITY Act, received mixed reviews from many industry thought leaders, including the Winklevoss twins, who believe it is too complex and lends too much discretion to federal regulators.

In their PAC announcement, the twins explicitly advocated for “Skinny Market Structure Bill” (capitalization in original) that codifies self-custody, protections for software developers, prohibits CBDCs, bans discrimination in banking, protects open banking, mandates permanent regulatory rulemaking, advances priorities of the Crypto Working Group report, and keeps costs to enter the regulated market low.

A16z declined to comment.

Partisan Action Committee

During the last cycle, Fairshake’s bipartisan approach was widely seen as successful, propelling 33 of the total 35 Fairshake-backed candidates into office in November. Many candidates who have been quiet on crypto became advocates, incentivized by large campaign donations, while several of those who had been hostile towards the industry toned down their critiques. This dynamic played a significant role in delivering the GENIUS Act last month, and has made market structure legislation a top priority issue moving forward.

Numerous sources who spoke with Brogan Law view the Digital Freedom Fund as a direct response to Fairshake, to which the twins previously gave nearly $5 million.¹ The language in the announcement is explicit in its support of President Trump’s crypto vision specifically, using MAGA-coded language like “the swamp,”²and singling out Haiti, a pet issue for the current administration that will be familiar with the Trump base. The language mirrors that which the twins use to describe their personal politics — rhetoric which has earned them a chummy relationship with the president, who compliments their “male model” appearances and “high iq.”

Despite this broadly held supposition, the twins have never criticized Fairshake publicly, and may ultimately support other PACs. Fairshake has so far raised over $140 million for the midterms, according to its own calculations, dwarfing the $21 million and change that the Digital Freedom Fund has publicly raised (formal disclosures with the FEC won’t be revealed until January). And it is entirely plausible that the turn is meant to complement, rather than compete, with the now-august crypto PAC.

Fairshake declined to comment.

Questions about Quintenz

Yet where there is smoke, you will sometimes find flame, and there is growing evidence of a schism. The CFTC promises to take on outsized importance in future crypto regulation, and the Winklevoss twins have become deeply embroiled in an ongoing conflict over its leadership.

As background, the twins’ Gemini Titan has long had a pending application for a designated contract market (DCM) license with the CFTC. The application was initially filed in 2020, but since then has been withdrawn and resubmitted. DCMs have been fetching nine-figure price tags of late, making this a high stakes process.

During the pendency of that application, though, the CFTC pursued action against Gemini for alleged violations of the Commodity Exchange Act related to bitcoin futures contracts. That suit settledjust seven days before Trump was inaugurated, when the crypto exchange was fined $5 million and received a permanent injunction without admitting fault. Lawyers for Gemini said that the firm had “no choice” but to settle at the time.

Unconfirmed rumors have circulated that Gemini has a close relationship with Acting CFTC Chair Caroline Pham, and were hoping she would be chosen as chair in the Trump administration. The speculation was fanned by the twins’ fervent opposition of Trump’s pick for CFTC chair, Brian Quintenz, in recent months.

Note, however, that Pham has publicly supported Quintenz’ nomination and has said since May that she intended to leave to the private sector. A CFTC spokesperson called the rumors a “silly distraction from the important mission of the CFTC.”

Whether the gossip is true or not, a battle has raged over Quintenz. The campaign first became public in the doldrums of July, when many in the industry were relaxing. Suddenly, according to Politico, the twins were bringing Dustin Gouker’s reporting on Quintenz to the White House in an attempt to spike his nomination. In August, the twins went on a press blitz to make their case, arguing that Quintenz supported prosecuting smart contract developers, faced conflicts of interest, and supported central bank digital currencies (CBDCs). A confirmation hearing had just been taken off the Senate Agriculture Committee’s schedule in late July, and it still has not been rescheduled.

And while murmurs about the origin of the beef still swirl, it is hard to watch this fight and not see a broader battle for control of crypto policy as a whole. On the one hand there are the old guard, like a16z, where Quintenz previously worked, and on the other the new, led by the Winklevoss twins.

Quintenz and a16z declined to comment on the twins’ claims. However, they are notably rebuttable: Quintenz called code a “First Amendment right” on the Bankless podcast in 2021, for example, and opposed a theoretical US CBDC in 2023.

Despite some controversy over emails Mr. Quintenz’ sent while still on the Kalshi board, briefings for incoming agency chairs are both legally protected and typical.

In response to the twins’ power ten, a flurry of industry groups rushed to Quintenz defense last week, urging the President to move forward with the confirmation in a co-signed letter. The outcome, though, remains undecided.

A Looming Democratic Threat

So is the Winklevoss new PAC a paradigm shift or simply a flash in the pan? Only time will tell for sure. Two Democratic party insiders who spoke to Brogan Law were dismissive of the effort saying that they understood the staff, who remain unknown, weren’t strategic enough to do serious damage, but perhaps it serves their interest to frame the growing storm thusly.

The Winklevoss twins, with one tenth the money, have already proven to be major players in the confirmation of one of crypto’s most consequential regulators. They’ve also earned the President’s admiration, while many other industry players have lost footing.

Still, the gambit has clear risk. Partisanship worked for the NRA, which, armed with culture war ammunition, won so many legal battles that it ran out of targets. But it worked less well for marketplace healthcare reform, which was originally pioneered by Republican Mitt Romney before becoming so toxic as a Democratic issue that it remains controversial today.

Only time will tell. But when it comes to the Winklevoss twins, I’m expecting to see more influence, not less.

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1

This perspective has also been shared in news coverage covering the announcement, like that in Politico.

2

Though according to the New York Times, perhaps we all are. Brogan Law Link: https://open.substack.com/pub/broganlaw/p/winning-elections-the-winklevoss?r=8a52v&selection=834531a0-8b22-44f5-a7e5-8e08cf266d4a&utm_campaign=post-share-selection&utm_medium=web&aspectRatio=instagram&textColor=%23ffffff&bgImage=true