Kenneth Dart has lost more than half the value of his US$7.62 billion Flutter Entertainment shareholding.

The Cayman Islands-based investor built the stake over 12 months at an estimated cost of US$7.62 billion, and by mid-August 2026 the shares were worth about US$3.35 billion, a loss of US$4.27 billion, according to an analysis of filings with the U.S. Securities and Exchange Commission (SEC) published in August by Casinos.com, a gambling industry news site. The Irish Times, which has tracked the stake since it was first disclosed, reported on 15 September 2026 that Flutter's shares had fallen 64% over the previous 12 months.

The loss is unrealised, meaning it is the gap between what Dart paid and what the shares would fetch today, and it becomes permanent only if he sells or if the price is still down when his derivative positions settle on 2 March 2028. It comes on top of a loss of more than US$700 million on a drug company he closed in 2018, and it sits alongside the announcement on 20 October 2026 that Flutter, the owner of Paddy Power, Betfair, Sky Bet and FanDuel, will cut up to 1,400 jobs in its UK and Ireland business after UK gambling tax rises. Dart has not commented publicly on the stake.

Dart owns Compass Media, publisher of the Cayman Compass, a competitor of The Caymanian Journal (TCJ).

How the stake was built

Dart first disclosed a 5% holding in Flutter in September 2025. Flutter's regulatory filings tracked the build-up to 20% by March 2026, 25% in April and 27% in May. By August his economic interest was close to 29.6%, with about 18.8 percentage points held as shares through his vehicle Candle Lake Limited and the rest through derivatives.

Those derivatives are cash-settled total return swaps entered through two further Dart vehicles, LBS Limited and Lake Michigan Limited. A Form 4 filed with the SEC on 14 August 2026 took the notional position under the swaps to 21,767,973 shares. Under their terms Dart must pay his counterparty any fall in Flutter's share price below the reference price at maturity, and collects any gain above it. If the shares are still down in March 2028, that is a second loss, in cash, on top of the fall in value of the shares he owns outright.

He kept buying as the price fell. The swap filings show new exposure added on 5 and 12 August 2026, at reference prices well below those on his earlier positions. The Irish Times reported on 15 September 2026 that his total economic interest had passed 30%, but that because 12.6 percentage points sat in swaps rather than shares he had avoided the mandatory takeover bid Irish rules require above that level. The same report said he had then made no purchases for a month, his longest pause since the stake was first disclosed.

Flutter's shares have fallen by about two thirds over the past year. The company cut its full-year guidance in August, reducing its revenue forecast by US$395 million to a midpoint of US$17.91 billion, and chief executive Peter Jackson was replaced by Dan Taylor on 1 October 2026.

The job cuts

Flutter's statement of 20 October said the redundancies, which remain subject to consultation, would fall on staff in Leeds and Dublin and on UK and Ireland employees at its hubs in Porto, Portugal and Cluj-Napoca, Romania. The 1,400 roles are about one in six of the 9,000 people in the division. Flutter put the cost of the restructuring at US$80 million to US$90 million, to be taken in the fourth quarter of 2026.

The company said the cuts answer the UK Government's 2025 Autumn Budget, which raised the duty on online gaming from 21% to 40% from April 2026 and raises the duty on online sports betting, excluding horseracing, from 15% to 25% from April 2027. Flutter has said the 2027 changes would cost it US$540 million in adjusted earnings before mitigation.

Kevin Harrington, chief executive of Flutter UK and Ireland, said in the statement: "The material increase in betting and gaming duties announced in the UK Budget last year has fundamentally changed the economic model of the regulated betting and gaming industry in the UK while helping to fuel the unlicensed, unregulated market." He added: "As we warned a year ago, we cannot fully absorb a rise of this magnitude without reducing our fixed cost base and therefore must restructure our business so that we can best position ourselves for the future."

A UK Government spokesman, quoted by This Is Money on 20 October, said the cuts were a commercial decision for Flutter and not for the Government.

The earlier loss

Dart NeuroScience, the San Diego drug company Dart founded in 2008, filed notice with the State of California on 7 December 2017 that it would lay off 265 employees and close permanently on 9 February 2018. The company said at the time that it had invested well in excess of US$700 million over a decade without generating adequate signs of human memory improvement. That loss was realised: the company closed and the money was not recovered.

More bets in gaming

Flutter is not Dart's only gambling position, and the others have moved against him too. A Form 13G filed with the SEC on 14 August 2026 showed Candle Lake holding 28.58 million shares, or 5.8%, of DraftKings, Flutter's main U.S. rival. The Irish Times reported on 15 September that DraftKings shares had fallen 42% over 12 months and Flutter's 64%, and put the combined value of the two stakes at US$6.18 billion.

In Sweden, Candle Lake was obliged to make a mandatory offer for online casino software company Evolution AB in August after its stake passed 30%. The offer, at SEK 695 a share, was the minimum Swedish law allows, and Candle Lake said it was not motivated by any intention to acquire all outstanding shares. Evolution's board rejected it. That position has gone the other way: the Irish Times reported Evolution's shares had risen close to 30% since Dart's holding crossed 30%.

The gaming positions were funded in part from an earlier win. Bloomberg reported in December 2025 that Dart had made about US$4 billion on British American Tobacco and Imperial Brands before selling down those holdings from April 2025 and moving into Flutter and Evolution.

What is open

Whether the Flutter loss becomes permanent depends on the share price on 2 March 2028, when the swaps settle, and on whether Dart sells, holds or keeps adding. He has given no public indication of which. Flutter has said it will report third-quarter results in November 2026.