Widow Sues Male Escort Agency, Alleging $6 Million Fraud

Marianne Flippo, the widow of an early Roblox programmer, has filed a lawsuit in Manhattan Supreme Court alleging that a male escort and his agency defrauded her of nearly $6 million by exploiting her grief, a rare genetic disorder, and a compromised mental state to pressure her into signing a fraudulent buyout agreement.

The suit names Gregg Starr, an employee of an agency called Cowboys 4 Angels, and alleges that he and agency employee Bridget Collins built Flippo's trust before convincing her that the only way to make their companionship arrangement permanent was to pay $10 million to buy Starr out of his contract. Flippo, who was newly widowed and managing money alone for the first time, suffers from vascular Ehlers-Danlos syndrome, a rare genetic disorder that makes her blood vessels and organs prone to tearing and leaves her unusually sensitive to alcohol and medication. People with the condition have an average life expectancy of 48 to 51 years; Flippo is 49.

According to court documents, Flippo's husband, Chad, joined Roblox when it was still a startup, earning multiple patents and building substantial wealth before dying by suicide in August 2024 after battling depression. The couple had been married 28 years and had three children. In December 2024, still grieving and needing to travel to Italy for a medication that had become unavailable in the U.S., Flippo asked a former colleague of her husband's for help finding an Italian-speaking companion. She was referred to Cowboys 4 Angels, which she initially believed provided personal assistants but later learned was an escort agency.

Flippo paid the agency $27,000 for Starr's assistance on the Italy trip, split into three $9,000 payments she now believes were structured to avoid IRS reporting requirements. By March 2025, she had agreed to pay roughly $150,000 for Starr to be exclusive with her, but broke up with him that October after learning he was seeing an ex-girlfriend. The agency kept calling, and she eventually agreed to speak with him again. By December 1, 2025, Starr had moved into her Upper West Side apartment, and she signed a formal Independent Contractor Agreement paying $368,000 for his companionship through May. In January 2026, she paid another $90,000 to extend the exclusivity period.

The lawsuit alleges that during a February 2026 trip to visit Starr's mother, who suffered from dementia, two agency employees showed up unannounced and pressed Flippo to drink at lunch despite knowing she was on medication following a recent surgery. After roughly five drinks, they produced an Exit Agreement requiring her to pay $10 million to end Starr's ties to the agency. Flippo said in a sworn affirmation that she was taken to a hotel room and had never seen the document before that day. The agreement states that under no circumstances has physical companionship been purchased for consideration.

Flippo tried twice to wire the $10 million, but both attempts were flagged as suspected fraud, first by JPMorgan Chase and then through Westpac. Starr then directed her to open a joint account at Charles Schwab, which she says let him access funds without triggering a bank's fraud review. She transferred $5.95 million into that account, and bank records filed with the court show Starr moved $5,719,010.37 of it into an account in his name alone within weeks, draining the balance to $12.61 by the end of June.

In her affirmation, Flippo said she was not capable or perceptive enough to know the statements were false but relied on what Starr said because she loved and trusted him. She said she now realizes she was foolish. The lawsuit describes Starr as a sociopath who lacks any conscience. Flippo was already a client of attorney Larry Hutcher for unrelated legal matters when Starr's demand for an additional $4 million came up. Hutcher said he looked into what had happened and concluded she was the victim of a horrific scheme. He added that she was still under the Svengali-like control of Starr. Starr had retained his own attorney to draw up an agreement for the additional funds, and Hutcher arranged a July 7 meeting.

Author

Delaney Sawyer

Society Reporter

Delaney Sawyer covers public affairs, politics, business, culture and daily news for Core Memo. The role focuses on verification, context, and clear explanations for readers.

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