Hedge Fund Co-Founder Buys $72M Mansion Amid Bitter Divorce Battle

John Overdeck, the 56-year-old co-founder of the hedge fund Two Sigma Investments, has purchased a sprawling $72 million waterfront mansion in Palm Beach, Florida. The acquisition was made through a Delaware LLC as Overdeck navigates one of the most expensive divorce proceedings in U.S. history.

The 16,000-square-foot estate is nearly triple the size of his former marital home and was reportedly renovated before Overdeck moved in. The property features six bedrooms, a large great hall with 26-foot ceilings, a travertine swimming pool, and a dock capable of accommodating a substantial vessel.

Records indicate that the LLC used for the purchase, Avocado Enterprises, was incorporated in Delaware shortly before the transaction. Matthew Siano, identified as the manager of the LLC, previously worked with Overdeck at Two Sigma for two decades, overseeing legal and compliance operations.

Overdeck is reportedly living at the new estate with his girlfriend, 42-year-old financier Kimia Shadrokh, who is a managing director at the investment bank Peakstone. Overdeck's attorney confirmed their relationship and new living situation, stating that Overdeck relocated to Palm Beach and began the relationship after the divorce process commenced.

Shadrokh and Overdeck have been seen together at events, including the American Academy of Achievement Summit, and their names appear on a $100,000 donation to the Palm Beach Police & Fire Foundation. Both Overdeck and Shadrokh listed the Palm Beach property as their home address when registering to vote in the spring.

This recent acquisition adds another layer to Overdeck's contentious divorce from his estranged wife, Laura, 56. The couple, married for nearly 20 years without a prenuptial agreement, is engaged in a legal battle over assets estimated to be worth billions.

Laura Overdeck is seeking approximately $6.2 billion, which represents a 35 percent stake in Two Sigma Investments. John Overdeck, whose net worth is estimated by Forbes at $8 billion, has offered his estranged wife about $723 million in cash. His legal team contends that Two Sigma, founded two years before their 2002 marriage, is not a marital asset, while Laura's lawyers argue it was merely a concept at the time of their wedding.

Laura Overdeck has accused her husband of attempting to hide assets, alleging he moved billions into Wyoming trusts with the help of Two Sigma employees prior to their separation. She has also claimed he withdrew $55 million from a joint account and secreted away a $72 million tax refund check.

Adding to the complexity, Laura Overdeck has been barred from testifying in her own defense after allegedly accessing her husband's emails and confidential communications with his lawyers. She is now limited to cross-examining John Overdeck during the proceedings.

Further legal entanglements include a lawsuit filed by their son's fencing coach against Laura Overdeck in 2024, alleging a smear campaign. That suit was later dismissed.