Winklevoss brothers increase ties with pro-Trump figures as Gemini posts heavy losses ahead of IPO

The Winklevoss twins are navigating a complex path of political networking and financial maneuvering as their crypto exchange Gemini faces mounting losses ahead of its planned public offering. Despite reporting a net loss of $282.5 million in the first half of 2025—a significant increase from the $41.4 million loss during the same period in 2024—the brothers are strengthening alliances with pro-Trump political groups and institutional partners like Nasdaq in an effort to position Gemini for a successful IPO in a challenging market

Financial performance

Gemini’s financial performance has raised eyebrows, with H1 2025 revenue of $68.6 million failing to keep pace with operational costs. The exchange’s net loss of $282.5 million during this period contrasts sharply with the previous year’s results, highlighting persistent profitability challenges. Despite this, Gemini aims for a valuation between $2.2 billion and $3.1 billion in its IPO, hoping to raise up to $433 million. The scale of these losses, however, could dampen investor confidence and complicate the public listing.

Political strategy and institutional partnerships

The Winklevoss brothers have actively engaged in political spending to foster a favorable regulatory environment. They have donated over $32 million to Republican causes in 2025 alone, including $21 million to the Digital Freedom Fund, a super PAC supporting pro-Trump and pro-crypto candidates. This political strategy aims to push for clearer crypto regulations and reduce legislative hurdles for Gemini’s operations.

Simultaneously, Gemini secured a $50 million investment from Nasdaq, which will also partner with the exchange to provide custody and staking services to institutional clients. This partnership, along with support from lead underwriters Goldman Sachs and Citigroup, lends credibility to Gemini’s IPO efforts despite its financial struggles.

Regulatory and market risks and factors to watch

Gemini continues to face regulatory scrutiny, particularly from the New York State Department of Financial Services (NYDFS), which fined the exchange $37 million in 2024 for compliance failures. The crypto market’s inherent volatility also poses risks, as sudden asset price swings could further impact Gemini’s custody business and revenue streams.

Key factors to monitor include:

• The sustainability of Gemini’s financial model amid ongoing losses.

• The impact of U.S. regulatory changes, including the pro-crypto policies fostered by the Trump administration.

• The effectiveness of Gemini’s partnerships with institutions like Nasdaq in attracting investor interest.

• The outcome of the Winklevoss brothers’ political donations in shaping a favorable regulatory landscape.

The Winklevoss brothers are leveraging political influence and institutional partnerships to offset Gemini’s financial challenges and regulatory risks ahead of its IPO. While the exchange’s valuation target remains optimistic, its ability to achieve long-term growth will depend on improving operational efficiency, navigating regulatory complexities, and capitalizing on the evolving crypto landscape. The outcome of this strategy will determine whether Gemini can transition from a loss-making platform to a publicly-listed industry leader.