One could argue that the road to nationwide online sports betting goes through Donald Trump Jr.
On Tuesday, Trump Jr. announced that his investment firm, 1789 Capital, had acquired a new stake in the gambling platform Polymarket, which is seeking to re-establish itself in the U.S. He also stated that he had joined the unicorn startup as a “strategic advisor.”
Bloomberg reported that the Polymarket investment is worth eight figures ($10 million to $99 million).
In January, Trump Jr. joined Kalshi, Polymarket’s main rival, as a strategic advisor. It’s unclear what financial incentives he has with Kalshi, which already offers nationwide sports gambling under federal jurisdiction. Robinhood offers online sports gambling, which it advertises as investing, via a Kalshi partnership.
Trump Jr.’s involvement in both Polymarket and Kalshi indicates that the public barbs between the two companies will likely come to an end.
Kalshi is reported to be worth $2 billion, while Polymarket, which also has the NFL’s Saquon Barkley as an investor, was worth at least $1 billion before the new Trump Jr. investment.
Another platform offering sports trading across the U.S. is Crypto.com, with which Trump Media & Technology Group has a deep business relationship.
There are other players in the emerging prediction markets sector, such as PredictIt and Railbird Exchange (which DraftKings, a traditional sports betting app, is reportedly in talks to acquire), but neither currently offers sports betting.
Trump Jr.’s Power in Sports Betting Sector
The sitting president’s son has become a powerful figure in U.S. sports betting, a market worth $13.7 billion in 2024, according to the American Gaming Association.
Earlier this year, Trump Jr. criticized Ohio Gov. Mike DeWine for a proposed sports betting industry tax increase. DeWine later dropped the idea.
Critics pointed to Trump Jr.’s potential conflict of interest in advising two rival firms in the prediction gambling space. More importantly, his recent moves give the appearance that his involvement is a crucial component in fighting the legal backlash arising from circumventing state gambling law.
Historically, states have regulated casino-style gambling, not the federal government.
“The fact that the prediction market route to regulatory success seems to be to appoint the president’s son to some vague position is so banana republic coded,” said Zak Akoo, journalist at the gambling industry publication Next.io.
To offer nationwide sports betting under the so-called prediction model, a company must receive a designated contract market (DCM) approval from the Commodity Futures Trading Commission.
Traditional online sports betting, which is player-against-the-house instead of peer-to-peer, is regulated at the state level. The sports betting prediction model has created a backlash from states and the commercial and tribal casino industries.
As of late 2025, online sports betting was still illegal under state law in California and Texas, the two largest untapped markets for the U.S. sports betting industry.
The Trump Jr.-backed prediction-style sports betting platforms will have access to those lucrative markets.
Addiction Just an Afterthought
Sports betting through a website or app, regardless of whether it’s player-versus-sportsbook or peer-to-peer, is highly addictive for many users.
State-regulated sports betting has some safeguards, but they have proven ineffective at preventing widespread problem gambling. For example, more than half of online sports bettors have chased their losses, and nearly 40% have felt ashamed by their betting behavior.
On average, a gambling addiction harms the lives of 8–10 people, including the family and friends of the person with problem gambling.
As lackluster as state regulation is for problem sports gambling, the federal government is and will be even more absent. Prediction-style sports betting platforms will do an even worse job of mitigating addiction than traditional betting apps.
It’s a chaotic and fast-evolving era for online sports betting, and Trump Jr. is taking full advantage. Unfortunately, vulnerable consumers and their families will get the short end of the stick.
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