Billionaire Kenneth Dart, a reclusive figure known for his strategic investments, has recently redirected his financial focus from the tobacco industry to the burgeoning world of sports betting. Dart, who resides in the Cayman Islands and is the heir to a plastic-cup fortune, made headlines with a $4 billion profit from his previous investments in Big Tobacco. Now, he has set his sights on the gambling sector.
Since April, the 70-year-old investor has divested billions from tobacco stocks, acquiring a significant stake in Flutter Entertainment, a major player in the sportsbook industry. This move complements his existing investment in Swedish online casino company Evolution AB, valued at approximately $2.9 billion.
From Tobacco to Gambling: A Strategic Shift
According to Kenneth Shea, a Bloomberg Intelligence analyst, Dart’s interest in “sin stocks” is a calculated strategy. “Sin stocks — they’re the stocks everyone’s supposed to hate, but they’re also the stocks everyone’s addicted to,” Shea explained. “It’s almost the opposite of the AI trade. They’re recession-proof.”
Dart’s reputation for making bold investment choices is well-documented. His previous bets on British American Tobacco (BAT) and Imperial Brands were particularly shrewd. Between 2020 and 2024, he invested approximately $8.4 billion in BAT through his holding company, Spring Mountain Investments.
“If they outlawed menthol, it would have clobbered the stock,” Shea noted. “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 surged to about $3.6 billion, with the company’s shares reaching their highest levels since 2018. This increase comes after Dart sold $7.7 billion worth of stock, including nearly $5.7 billion since April 30 alone.
Challenges in the Gambling Sector
Despite his past successes, Dart’s recent foray into the gambling sector has encountered challenges. His $2.5 billion investment in Flutter Entertainment, owner of brands like FanDuel and Paddy Power, has not yet paid off. In the two months since Dart disclosed his 5.6 percent stake, Flutter’s shares have plummeted by about 25 percent, partly due to a costly earnings miss in November.
Flutter faces mounting competition from prediction market firms such as Kalshi and Polymarket. In response, FanDuel plans to launch its own prediction market product next month, a move that could potentially stabilize its market position.
Similarly, Evolution AB has seen its shares decline by about 35 percent since Dart first revealed his investment in August 2024. As of September 30, Dart held a 20.5 percent stake in the online casino company.
A History of Unconventional Investments
Dart’s penchant for offbeat investments is nothing new. Over the years, he has amassed wealth by investing in diverse sectors, including sovereign debt, Caribbean real estate, and biotechnology. His family’s legacy in the plastics industry began with the development of foam cup mass-production technology, a business that laid the foundation for Dart’s financial empire.
In 1994, Dart renounced his American citizenship and relocated to Belize. A year later, his proposal to convert his Sarasota, Florida property into a Belizean consulate was rejected by the US State Department, prompting his move to the Cayman Islands. There, he has become one of the largest private landowners, with a real estate portfolio spanning the Caymans and six US states, valued at over $1 billion.
While Dart’s latest investments in the gambling industry face hurdles, his track record suggests he may yet turn these ventures into profitable opportunities. As the gambling sector continues to evolve, Dart’s strategic decisions will be closely watched by industry analysts and investors alike.
