DraftKings and FanDuel compete for U.S. online gamblers, but they also furiously lobby together—and now share one especially large investor you may not have heard of.
That billionaire, Kenneth Dart, has quietly built huge stakes across the sector. Americans lost $27 billion to state-sanctioned online gambling in 2025, and losses this year are on pace to set a new record.
According to The Irish Times, the 71-year-old Dart recently built a 31% economic interest in Flutter, FanDuel’s parent company. August filings reportedly show he has also acquired roughly 6% of DraftKings.
He also owns more than 30% of Evolution AB, a Swedish supplier for both DraftKings and FanDuel. Evolution is best known for its so-called “live online casino” products, in which real humans deal gambling games from studios that are streamed to users’ mobile devices.
The Irish Times reported that Dart has paused acquiring more of Flutter for the first time in nearly a year. He initially held just 5% equity in Flutter.
Other Vice-Related Investments
The report described him as a “reclusive billionaire” who also has large investments in tobacco. It’s a notable component of his wealth, as U.S. public health experts have compared online sports betting marketing to the tactics of “big tobacco” a generation ago.
Another interesting part of his Forbes-estimated $4-billion-plus net worth: His family’s Dart Container also owns Solo Cup Company, maker of the ubiquitous red Solo Cup, a staple of U.S. college drinking culture. Alcohol is another product known to be addictive.
Dart was born in Michigan but is reportedly now based in the Cayman Islands.
Why This Matters
Former U.S. Surgeon General Jerome Adams last month described online sports betting as the “new opioid crisis.” While CEOs of companies in the online gambling sector are often well known, people should know who the most powerful men behind them are. Ken Dart is one of them.
Dart’s recent bullish bets on DraftKings and Flutter, despite huge share-price declines over the past year, could be a bet against the legality of so-called “sports event contracts” on prediction markets such as Kalshi and Polymarket. While DraftKings and FanDuel each launched their own prediction market in the U.S., Kalshi and Polymarket boast much greater sports prediction-style gambling activity.
In fact, Kalshi has been in talks to raise money at a $40 billion valuation, which would value it at more than DraftKings and Flutter’s current market capitalizations combined.
Dart has not publicly explained whether prediction-market regulation factors into his investments. But another prominent investor who bought both DraftKings and Flutter has made that wager explicit.
Michael Burry, famed for his bet against the U.S. housing market before the 2008 crash, recently disclosed purchases of Flutter and DraftKings. Burry described prediction markets as operating through a regulatory “loophole” and said he expects them eventually to face regulation and taxation. Kalshi recently suffered a huge loss at the Ninth Circuit, partly validating Burry’s thesis.
On the flip side, online betting products are reviled by many of their core users, suggesting choppy waters ahead for the U.S. sector. Legal sports betting is unpopular.
Nonetheless, prediction markets are still growing, thanks in part to financial ties to Donald Trump Jr. and endorsements from celebrities such as LeBron James and Sydney Sweeney. Some Silicon Valley elite are also all in, with billionaire Peter Thiel’s Founders Fund also a major Polymarket investor.
Meanwhile, other billionaires have warned about what they see as the great danger of both prediction markets and house-banked sports betting: young people treating it as investing, not gambling.
