Billionaire Kenneth Dart Now Holds Major Stakes in Both FanDuel's and DraftKings' Parent Companies
Billionaire investor Kenneth Dart has built simultaneous, sizable positions in both companies that own the two largest U.S. sportsbook brands — Flutter Entertainment, the parent of FanDuel, and DraftKings itself — a combined bet worth roughly $6.18 billion, according to reporting confirmed this week. Dart's Flutter stake reached approximately 31.4% by mid-September, while a 5.8% DraftKings position first surfaced in mid-August, putting the reclusive investor on both sides of the industry's biggest rivalry at once.
How the stake is structured
More than a third of Dart's Flutter position is held through cash-settled equity swaps and other derivatives rather than direct share ownership, a structure that keeps his direct equity below the 30% threshold that would trigger a mandatory takeover bid under Irish law, where Flutter is incorporated. Dart crossed 30% total economic interest in Flutter in late July or August, according to the reports, and has reportedly held roughly a monthlong pause in further Flutter purchases — his longest inactive stretch since his position first became public about a year ago.
Both stocks have struggled over the past year: Flutter shares are down roughly 64%, and DraftKings shares are down about 42%, over the trailing twelve months cited in the reporting, meaning Dart's Flutter position alone carries a substantial unrealized paper loss even as its size has grown.
Why it matters to bettors
Flutter has also cut its full-year profit forecast and seen the departure of longtime chief executive Peter Jackson in the past month, while both Flutter and DraftKings face growing competitive pressure from prediction-market platforms like Kalshi and Polymarket, which have expanded rapidly into sports-outcome contracts this year. A major shareholder holding meaningful positions in both leading legacy sportsbook operators simultaneously — rather than backing one against the other — is an unusual dynamic that could factor into how each company approaches capital allocation, leadership decisions, and its competitive response to the prediction-market threat, though neither company has commented publicly on Dart's specific intentions.
For everyday bettors, ownership changes at the corporate level don't directly move the odds or promotions on either app, but shifts in shareholder pressure can eventually influence pricing strategy, marketing spend, or M&A activity at operators this large — dynamics this site's news section will continue to track as they develop.