Kenneth Dart Nurses $4.27bn Paper Loss On Flutter Entertainment Stake

^{A Paddy Power betting shop in Leeds. Flutter Entertainment, which owns Paddy Power, has seen its US-listed shares fall 66% over the past year. (Photo: Mtaylor848 / Wikimedia Commons)}

Cayman Islands investor Kenneth Dart is sitting on a paper loss of at least $4.27bn on his stake in Flutter Entertainment, according to US Securities and Exchange Commission filings that track his continued build-up of shares in the online casino and sports betting group behind Paddy Power and FanDuel.

Dart, 71, began accumulating Flutter stock in September 2025 and has since amassed an economic interest of close to 29.6%, according to disclosures filed with the SEC and Ireland's Companies Registration Office. Flutter is incorporated in Ireland but has traded on the New York Stock Exchange since moving its primary listing there in 2024.

A Form 4 filed with the SEC on 14 August 2026 shows Dart's investment vehicle Lake Michigan Limited entering a further total return swap covering 51,595 notional Flutter shares at a reference price of $97.1957, taking the aggregate notional position held through LBS Limited and Lake Michigan Limited to 21,767,973 shares. The filing follows two earlier swaps of 885,900 and 817,815 shares reported on 7 August, both entered through the same vehicles.

All of the swaps disclosed by Dart's entities in the past two weeks are scheduled to terminate on 2 March 2028, when they will be cash-settled. Under their terms, Dart is obligated to pay his counterparty any decline in Flutter's share price below the reference price at maturity, and stands to collect any gain above it.

Direct Shares Down More Than $4bn

Roughly 18.8 percentage points of Dart's economic interest is held through directly owned shares in Candle Lake Limited, his primary holding vehicle, with the remainder built through the swaps. Flutter's own regulatory filings, published via the London Stock Exchange's Regulatory News Service, have tracked the build-up in stages: an initial 5% stake disclosed in September 2025, 20% by March 2026, 25% in April and 27% in May.

Flutter shares have fallen 66% over the past 12 months and 21% in the past six months, leaving the company with a market capitalisation of roughly $17bn. Dart spent an estimated $7.62bn acquiring his direct shareholding at the average price paid during his buying periods, a sum now worth about $3.35bn at current prices, producing the $4.27bn paper loss on the shares alone.

The swap positions carry additional exposure. Because they are cash-settled rather than physically backed, any further decline in Flutter's share price before the March 2028 maturity would add to the amount Dart owes his counterparties, on top of the losses already recorded on his direct holding.

Dart's swap filings show he added exposure to Flutter on 5 and 12 August 2026, even as the stock traded well below the reference prices set on his earlier positions.

Leadership Change And Cut Guidance

The stock's slide has coincided with a rocky period for Flutter. Chief executive Peter Jackson is stepping down after almost nine years in the role, with Dan Taylor, head of the group's international division, set to take over as CEO at the start of September. Flutter also cut its full-year guidance, reducing its revenue forecast by $395m to a midpoint of $17.91bn and trimming its adjusted EBITDA guidance by $210m to $2.65bn.

Investors have grown more cautious about Flutter's FanDuel-led US growth story amid intensifying competition and concern that prediction market operators, which offer sports-linked contracts outside traditional gambling licensing, could draw activity away from regulated sportsbooks.

Who Is Kenneth Dart?

Dart built his fortune through the Dart Manufacturing Company, founded by his grandfather in 1937, and decades of investing in distressed sovereign debt, a strategy that earned him the nickname 'vulture investor' in financial circles. His Flutter position adds a large public-markets bet to a portfolio built mostly on private holdings and debt restructurings.

None of Dart's swap positions carry voting rights, and his direct shareholding remains below the 30% threshold that would trigger a mandatory takeover offer for the whole company under Irish takeover rules. Whether he continues adding to the position, or whether Flutter's shares recover before the swaps mature in 2028, will determine how much of the paper loss becomes permanent.