Reclusive Cayman Islands-based billionaire, Kenneth Dart has solidified his credentials as a contrarian investor in the past three months or so with a growing bet on Paddy Power owner Flutter Entertainment.
The septuagenarian, who first disclosed a 5 per cent stake in the group in late September, has since tripled down – even as the stock has lost almost a quarter of its value in the meantime.
Flutter disclosed this week that two Dart vehicles – Lake Michigan Ltd and LBS Ltd – now have a combined 15 per cent stake in Flutter, worth $5.65 billion (€4.86 billion) making him the biggest shareholder in the group. (About a third of the holding via financial derivatives called equity swaps, giving him economic exposure without owning the shares directly.)
The world’s largest betting company cut its 2025 earnings before interest, taxes, depreciation and amortisation (Ebitda) forecast in November by $380 million to €2.92 billion driven by another long winning streak by gamblers that increased its payouts. Sentiment was further dented by the British government’s move in its budget in November to increase taxes on online betting, which Flutter said would knock hundreds of millions off its annual profits.
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Flutter, which owns FanDuel, the top sports betting company in the US, and rival DraftKings, have also seen their shares dented by being late arrivals to the fast-growing predictions market, where people can place wagers on everything from elections and the weather to whether a new phone will sell a million units.
Dart’s increasing stake in Flutter suggests confidence that Flutter’s own new predictions product – announced late last year in partnership with CME Group – will be able to take on the two existing US prediction market leaders, Polymarket and Kalshi.
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Not all investors would share such optimism. But not all investors are like Dart, whose family wealth stems from his grandfather founding Dart Manufacturing, the world’s largest maker of Styrofoam cups.
Over the course of decades, Dart expanded his wealth by buying distressed sovereign debt from countries including Argentina, Brazil and Greece – often engaging in lawsuits to squeeze more out of debtors seeking to restructure their borrowings.
He is also the largest shareholder in Evolution, a Swedish online casino tech company, and in recent years has amassed big stakes in tobacco giants British American Tobacco and Imperial brands – defying an ethical exodus from such companies.
He’s not one to follow the crowd.
