Key Takeaways
- • Stephen Deckoff, founder of Black Diamond Capital Management, acquired Jeffrey Epstein's two Caribbean islands (Little St. James and Great St. James) for $60 million through SD Investments LLC, representing approximately 50% below the initial asking price.
- • Deckoff is seeking a $5.757 million refund from the U.S. Virgin Islands tax authority (VIBIR) for a claim filed in November 2025, citing lack of approval or denial of his petition—a legal dispute distinct from the property acquisition itself.
- • Development plans call for construction of a 25-room luxury resort designed to generate tourism revenue and economic activity in the U.S. Virgin Islands, with targeted opening in 2025.
- • A significant portion of sale proceeds are directed to the U.S. Virgin Islands government under a prior settlement agreement; Epstein's estate agreed in November to pay the territory over $105 million to settle sex trafficking and exploitation claims, with the islands sale generating additional government revenue.
- • Deckoff, a long-term Virgin Islands resident (10+ years), positioned the acquisition as an economic development opportunity while acknowledging the islands' contentious history.
Summary
Stephen Deckoff, the billionaire founder of private equity firm Black Diamond Capital Management, has purchased the two private islands formerly owned by Jeffrey Epstein for $60 million—a transaction representing substantial savings versus the initial asking price. The acquisition, executed through Deckoff's investment vehicle SD Investments LLC, transferred title to Little St. James and Great St. James in the U.S. Virgin Islands. According to multiple sources, Deckoff negotiated the purchase at approximately 50% below the listed asking price, demonstrating favorable terms in what remains a uniquely sensitive real estate transaction.
The property purchase has been complicated by a separate legal matter. Deckoff filed a refund claim with the U.S. Virgin Islands Bureau of Internal Revenue (VIBIR) in November 2025, demanding $5,757,038. According to available reports, the dispute centers on VIBIR's failure to formally approve or deny his petition, creating a procedural impasse that has prompted legal escalation. This refund claim operates independently from the island acquisition itself and reflects post-purchase tax or settlement-related disagreements.
Deckoff's stated development strategy emphasizes economic utility rather than controversy. Plans include construction of a 25-room luxury resort targeting the high-end hospitality market, with anticipated completion in 2025. The project framework positions the islands as engines for regional tourism growth and employment creation. Deckoff, who has maintained residency in the Virgin Islands for over a decade, framed the acquisition as a state-of-the-art hospitality development that would respect environmental preservation standards.
The transaction structure incorporates significant government benefit. A material portion of the $60 million purchase price flows to the U.S. Virgin Islands government under a pre-existing settlement agreement between Epstein's estate and territorial authorities. In November 2024, Epstein's estate entities agreed to pay the Virgin Islands government more than $105 million to settle claims arising from sex trafficking and child exploitation. The settlement agreement explicitly required that 50% of island sale proceeds, plus an additional $450,000 designated for environmental remediation on Great St. James, be paid to the government. This structure ensures that territorial authorities receive direct financial benefit from Deckoff's acquisition, creating aligned interests between the new owner and regional stakeholders.
The property purchase has been complicated by a separate legal matter. Deckoff filed a refund claim with the U.S. Virgin Islands Bureau of Internal Revenue (VIBIR) in November 2025, demanding $5,757,038. According to available reports, the dispute centers on VIBIR's failure to formally approve or deny his petition, creating a procedural impasse that has prompted legal escalation. This refund claim operates independently from the island acquisition itself and reflects post-purchase tax or settlement-related disagreements.
Deckoff's stated development strategy emphasizes economic utility rather than controversy. Plans include construction of a 25-room luxury resort targeting the high-end hospitality market, with anticipated completion in 2025. The project framework positions the islands as engines for regional tourism growth and employment creation. Deckoff, who has maintained residency in the Virgin Islands for over a decade, framed the acquisition as a state-of-the-art hospitality development that would respect environmental preservation standards.
The transaction structure incorporates significant government benefit. A material portion of the $60 million purchase price flows to the U.S. Virgin Islands government under a pre-existing settlement agreement between Epstein's estate and territorial authorities. In November 2024, Epstein's estate entities agreed to pay the Virgin Islands government more than $105 million to settle claims arising from sex trafficking and child exploitation. The settlement agreement explicitly required that 50% of island sale proceeds, plus an additional $450,000 designated for environmental remediation on Great St. James, be paid to the government. This structure ensures that territorial authorities receive direct financial benefit from Deckoff's acquisition, creating aligned interests between the new owner and regional stakeholders.
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