Marianne Flippo, widow of Roblox inventor Chad Flippo, has filed a lawsuit accusing male escort Gregg Starr of defrauding her out of nearly $6 million in a complex case involving grief, manipulation, and substantial financial loss. The lawsuit, filed in Manhattan Supreme Court, alleges that Starr convinced Flippo to buy out his $10 million contract with the escort agency Cowboys 4 Angels under the guise of a romantic relationship.
Chad Flippo, a computer programmer credited with creating and patenting critical software for the successful online platform Roblox, died by suicide in August 2024 after battling depression. His death left Marianne Flippo, 49, mourning not only her husband but also coping with vascular Ehlers-Danlos syndrome, a genetic disorder that weakens connective tissues and reduces life expectancy. Shortly after his death, Flippo sought companionship for a necessary trip to Italy to obtain rare medication disrupted by the Russia-Ukraine conflict, which led her to hire Starr through Cowboys 4 Angels.
According to court documents, Flippo was unaware that the agency was an escort service when she initially contracted Starr, paying $27,000 for his company on the trip. Starr, described as an attractive, silver-haired man fluent in Italian, reportedly kept the relationship professional during the trip, but following continued contact initiated by the agency, the pair began an on-and-off relationship. Starr moved into Flippo’s New York apartment in December 2024, during which time she paid him over $450,000 for exclusivity, the suit alleges.
The legal complaint claims the relationship deteriorated during an early 2025 trip to Atlanta, when Flippo, under the influence of medication and alcohol, was pressured into signing a $10 million “Exit Agreement” to buy Starr out of his escort contract. Flippo alleges that when she attempted a wire transfer, her bank flagged the transaction as suspicious. Eventually, she was persuaded to open a joint account with Starr, transferring nearly $6 million into it. The lawsuit states Starr subsequently transferred $5.7 million out of the joint account to one solely under his control and began rapidly spending the funds.
Flippo’s attorney, Larry Hutcher, called the transaction suspicious and described Starr as a “common criminal” after his attempts to negotiate the remaining $4 million allegedly failed and Starr threatened to withhold the money. Starr, when reached, denied accusations of wrongdoing, stating that much of the money was spent on expenses related to Flippo and charitable donations, including $1 million given to churches in Midtown Manhattan and Atlanta.
The financial fallout from the alleged scam coincides with Flippo’s purchase of a landmarked six-story mansion in Manhattan’s Kips Bay neighborhood. Records show she closed on the historic Gilded Age beaux-arts property on April 30, 2025, paying $15.9 million—a significant investment within months of the dispute with Starr unfolding. The 1903 home, known as the Lanier House and previously owned by prominent socialites, features 12 bedrooms, nine-plus bathrooms, a wine cellar, a wellness floor, and an oak-paneled elevator. Despite the acquisition, Flippo continues to maintain a residence in New Hampshire.
This case highlights the intersection of personal vulnerability and high-stakes financial dealings, with Flippo seeking legal recourse to recover her losses and prevent further dissipation of funds. Starr, for his part, characterizes their relationship as tumultuous and resists the fraud allegations through his representatives. The matter remains before the courts as both parties navigate the aftermath of a relationship that has drawn national media attention.