Trump News: Kalshi Ends Trump Jr. Advisory Role
The trump news out of the prediction markets industry on Thursday was a split that had been months in the making: Kalshi has ended Donald Trump Jr.’s advisory contract after his venture capital firm, 1789 Capital, deepened its investment in Kalshi’s biggest rival, Polymarket. The company confirmed the decision to Reuters on November 12, describing it as a mutual business decision and thanking Trump Jr. for his work. But the reason given leaves little room for doubt about what drove it. The president’s eldest son joined Kalshi as a strategic adviser in January 2025, shortly after his father’s return to the White House, and within months his firm was backing the very competitor Kalshi is fighting for dominance of a booming new market.
A Kalshi spokesperson put it plainly in a statement to Reuters: “We have mutually agreed to end Don’s advisory role after his firm’s significant investment in a competitor this past summer. We are grateful for his contributions in helping us market Kalshi to more customers.” The company said the conversations about ending the contract began in August, when 1789 Capital led Polymarket’s most recent funding round. For a firm that has spent the year positioning itself as the largest prediction market in the world, keeping the son of the president on its advisory board while his firm poured hundreds of millions of dollars into its arch-rival had become impossible to defend.
The Breakup
Kalshi’s decision was confirmed on Thursday, November 12, when a company spokesperson told Reuters that the advisory contract had been terminated. The news was first reported by Reuters and quickly picked up across the business press, with the New York Post, CoinDesk, and other outlets confirming the same account: the two sides had agreed to part ways after 1789 Capital increased its stake in Polymarket over the summer. Neither Polymarket nor Trump Jr. immediately responded to Reuters’ requests for comment, and no statement was issued by 1789 Capital about the end of the Kalshi role.
The language from Kalshi was carefully chosen. The company stressed that the decision was mutual, that the talks had been going on since August, and that it was grateful for Trump Jr.’s help in bringing customers to the platform. That is the language of a business divorce conducted without public rancour, and it fits what is known about the timeline: the relationship did not end in a sudden rupture, but in a slow unwinding that began the moment 1789 Capital’s Polymarket investment became public.
What makes the split notable is not just the money involved but the position Trump Jr. occupied. He was not a passive investor. He was a paid strategic adviser to Kalshi, a role the company’s chief executive, Tarek Mansour, had described as focused on market strategy, growth, partnerships, and audience expansion. At the same time, he was a partner at 1789 Capital, the firm that was leading Polymarket’s fundraising, and a member of Polymarket’s own advisory board. In the prediction markets business, where the two companies are fighting over the same users, the same event contracts, and the same regulatory future, advising both sides at once was untenable.
The $300 Million Bet on Polymarket
The investment at the centre of the split is large by any measure. In September, 1789 Capital agreed to contribute approximately $300 million toward a Polymarket funding round that aimed to raise $1 billion and would value the company at around $21 billion, up from close to $15 billion before the deal. The firm had already invested about $200 million in Polymarket earlier, bringing its total commitments toward the round to roughly $500 million, according to figures confirmed by a spokesperson for 1789 Capital at the time. The September figures described planned financing and commitments rather than a final ownership stake, but the scale of the commitment was clear: 1789 Capital was not making a small side bet on Polymarket. It was leading the round.
The size of the bet explains why Kalshi could not look the other way. Polymarket is not a minor rival. It is the company that became famous during the 2024 presidential election, when its markets on the outcome of the race drew enormous trading volume and attention, and it has since become the most recognisable name in prediction markets. Kalshi, by contrast, is the largest prediction market operating under a federal licence in the United States, and it has spent the past year arguing that its regulated status gives it an advantage over its rival. The two companies are now competing directly for the same traders, the same sports and politics contracts, and the same institutional backing, and a $300 million investment from the firm of Kalshi’s own adviser was a vote of confidence in the other side.
The valuations tell the same story. The New York Post reported that Kalshi has been in talks to raise funds and is eyeing a valuation of $40 billion, while Polymarket is aiming for a valuation above $20 billion. Both companies are riding a wave of interest in prediction markets that began with the 2024 election and has only grown since, as traders, sports fans, and political watchers have flocked to platforms that let them put money on the outcome of real-world events.
A Timeline of Two Advisory Roles
The story of Trump Jr.’s twin roles begins in January 2025. Shortly after President Trump was sworn in for his second term, Kalshi named Trump Jr. as a strategic adviser and gave him an equity stake reportedly worth approximately $300,000 at the time, when the platform was valued at under $2 billion. The appointment made sense for Kalshi: the president’s son was one of the most prominent voices in the movement that had just won the election, and prediction markets had gained prominence in the United States in the run-up to that election, particularly after Trump won re-election. Having Trump Jr. on board was a signal that Kalshi was connected to the new administration and to the audience that had made prediction markets famous.
The second role followed seven months later. In August 2025, Trump Jr. joined Polymarket’s advisory board, at the same time as an initial investment in the company from 1789 Capital. For a year, he held both positions: strategic adviser to Kalshi and advisory board member at Polymarket. The arrangement was unusual, but it was not secret. Both companies knew about it, and the market treated it as a curiosity rather than a scandal.
The balance broke in August 2026, when 1789 Capital led Polymarket’s most recent funding round. That was the moment Kalshi’s patience ran out. The company said the discussions about ending Trump Jr.’s contract began that month, and the decision was confirmed on November 12, three months later. The delay suggests the split was negotiated rather than imposed: Kalshi thanked Trump Jr. publicly, stressed that the decision was mutual, and credited him with helping to market the platform. But the underlying fact is simple. A firm cannot keep as its adviser a man whose own investment company is leading a $1 billion funding round for its biggest rival.
The Prediction Market Rivalry
To understand why the split matters, it helps to understand what prediction markets are and why they have become one of the most contested corners of American finance. A prediction market lets users trade contracts tied to real-world outcomes, including politics, sports, and economic events. A trader who believes a candidate will win an election, a team will win a championship, or the Federal Reserve will cut interest rates can buy a contract that pays out if the prediction is right, and sell it if the outlook changes. The prices on these markets are often treated as a live measure of what the crowd believes, and during the 2024 election they became a closely watched alternative to traditional polling.
Kalshi and Polymarket are the two giants of the sector, but they operate in different worlds. Kalshi is a federally regulated exchange, licensed by the Commodity Futures Trading Commission, and it has built its business on the argument that regulation makes its markets safer and more legitimate. Polymarket, by contrast, built its audience outside the American regulatory system, operating from overseas and settling its trades in cryptocurrency, and it became famous precisely because it was willing to offer the election markets that American regulators had long resisted. The two companies now compete directly for the same users, and the rivalry has become personal as well as commercial, with each side arguing that its model is the future of the industry.
The business news around both companies in recent months has been dominated by fundraising. Kalshi’s reported pursuit of a $40 billion valuation and Polymarket’s push past $20 billion reflect a sector that investors believe is still in its early stages, with sports betting, election markets, and economic event contracts all seen as growth areas.
The Regulatory Fight Ahead
The split also comes at a moment when the regulatory future of prediction markets is unresolved. Operators of prediction markets face disputes over state gambling laws and over the federal oversight of event contracts, and both Kalshi and Polymarket have been drawn into legal fights about whether their products are financial instruments or gambling. State regulators have challenged Kalshi’s right to offer sports event contracts, arguing that they amount to sports betting that should be licensed by the states. Kalshi has argued that its federal licence pre-empts state law, and the question is now being litigated in courts across the country.
That fight is one reason the Trump Jr. connection mattered so much to Kalshi in the first place. A prediction market operating under a federal licence needs political allies, and the president’s son was a powerful one. It is also a reason the split may matter beyond the two companies. Trump Jr.’s move to Polymarket’s advisory board, and his firm’s $300 million investment in the company, ties the Trump family’s political network to a platform that has operated outside the American regulatory system, at a moment when the administration is shaping the rules that will govern both companies.
What Happens Next
For Kalshi, the immediate task is to replace the political capital it has just lost. The company is reportedly in talks to raise funds at a $40 billion valuation, and it will need to show investors that it can grow without the Trump connection that helped define its public image. Its argument will be that its federal licence, its regulated status, and its growing volume speak for themselves, and that the loss of one adviser, however prominent, does not change the fundamentals of its business. The company’s public statement was designed to make that point: the split was mutual, the relationship had run its course, and the business goes on.
For Trump Jr. and 1789 Capital, the split clarifies a position that had become contradictory. He remains on Polymarket’s advisory board, and his firm remains one of its largest backers, with roughly $500 million committed to its latest funding round. The question now is whether that bet pays off, and whether Polymarket can convert its fame from the 2024 election into a durable business that justifies a $21 billion valuation. The company has not commented on the Kalshi split, and Trump Jr. has not commented either, but their silence is itself a statement: the choice has been made, and it is Polymarket.
Source: Reuters