1 hour ago
2
By Dylan Sloan
December 5, 2025 — 6.20am
Billionaire Kenneth Dart, the reclusive, Cayman Islands-based heir to his family’s eponymous plastic-cup fortune, made $US4 billion ($6.1 billion) from a contrarian bet on Big Tobacco. Now, he’s turned his attention to another vice.
Since April, the 70-year-old investor has unloaded billions in tobacco stocks and bought a major stake in sportsbook operator Flutter Entertainment. That complements a position in Swedish online casino firm Evolution AB that he began building last year, currently worth about $US2.9 billion.
Dart, whose father and grandfather first developed the technology to mass-produce foam cups, relinquished his American citizenship in 1994.
“Sin stocks — they’re the stocks everyone’s supposed to hate, but they’re also the stocks everyone’s addicted to,” Bloomberg Intelligence analyst Kenneth Shea said in an interview. “It’s almost the opposite of the AI trade. They’re recession-proof.”
Dart, who’s so seldom seen that there are few photos of him publicly available, made wagers on UK-based cigarette makers British American Tobacco and Imperial Brands that proved to be shrewd. From 2020 to 2024, he spent about $US8.4 billion buying a position in then-laggard BAT through his holding company Spring Mountain Investments, according to a Bloomberg News analysis.
Loading
BAT shares performed poorly during the administration of former US President Joe Biden, who pushed to prohibit the sale of menthol-flavoured cigarettes, Shea said.
“If they outlawed menthol, it would have clobbered the stock,” Shea said. “I can fully understand why he’d take a bet on BAT, particularly after Trump got elected.”
The value of Dart’s remaining stake in BAT has climbed to about $US3.6 billion as the company’s shares have risen to the highest since 2018. And that’s after he already sold $US7.7 billion of stock, including nearly $US5.7 billion since April 30 alone.
Imperial Brands’ shares have risen about 120 per cent since Dart first disclosed a stake in 2021. Those gains helped push his net worth to $US13.7 billion from about $US6.6 billion in May 2024, according to the Bloomberg Billionaires Index.
A spokesperson for Dart didn’t respond to a request for comment.
Poor performers
By contrast, Dart’s investment in Flutter has been ill-timed. In the two months since the billionaire disclosed spending about $US2.5 billion buying a 5.6 per cent stake through another Cayman Islands-based holding company, the owner of brands including FanDuel and Paddy Power has seen its shares fall about 25 per cent, fuelled in part by a costly earnings miss earlier in November.
Making offbeat bets is nothing new for Dart, who has made billions investing in diverse sectors including sovereign debt, Caribbean real estate and biotechnology.Credit: The New York Times
Flutter has faced increased pressure from prediction markets firms including Kalshi and Polymarket. FanDuel is planning to roll out its own prediction market product next month.
Loading
Evolution has also performed poorly, with shares down about 35 per cent since Dart first disclosed a position in the online casino company in August 2024. He owned a 20.5 per cent stake as of September 30, according to a filing.
Making offbeat bets is nothing new for Dart, who has made billions investing in diverse sectors including sovereign debt, Caribbean real estate and biotechnology.
Dart, whose father and grandfather first developed the technology to mass-produce foam cups, relinquished his American citizenship and moved to Belize in 1994. A year later, the US State Department rejected a proposal to turn his property in Sarasota, Florida, into a Belizean consulate, which would have allowed him to continue living there tax-free.
He later relocated to the Cayman Islands, where he’s become one of the island nation’s largest private landowners. Alongside his equity investments, Dart controls a real estate portfolio in the Caymans and six US states valued at more than $US1 billion, according to Bloomberg’s wealth index.
Most Viewed in Business
Loading
