Roblox Millionaire’s Widow Thought Her Younger Escort Wanted Love — Then Two Banks Block a $10M Transfer, and What Happens Next Is Even More Shocking
Marianne Flippo lost her husband of 28 years in August 2024. She also lost the only person who had ever managed the fortune he built as an early programmer at Roblox.
Months later, the grieving mother of three paid a stranger to accompany her on a trip overseas. She says it was only supposed to be one trip.
Instead, she claims that stranger ended up living in her Manhattan apartment and sitting on a $10 million payday. By the time anyone stepped in, nearly $6 million of her late husband’s money was gone in what she now calls a horrible scheme.
Flippo, 49, filed suit on Monday, Sept. 14 in New York State Supreme Court in Manhattan against Greggory Blaine Starr, according to the New York Post. Starr is a 38-year-old West Point graduate and Army veteran she met through Cowboys4Angels, an agency that books male escorts for women.
Her late husband, Chad Flippo, was a programmer with multiple patents who joined Roblox, the gaming platform wildly popular with kids, while it was still a startup.
Childhood sweethearts together since age 13, the couple raised three children before Chad died by suicide on Aug. 5, 2024. Marianne inherited his wealth despite, she says, never handling the family’s finances.
She also lives with vascular Ehlers-Danlos syndrome, a rare genetic disorder that leaves blood vessels and organs fragile. One of the few medications she tolerates became scarce in the U.S. after Russia invaded Ukraine. So, in December 2024, she reportedly planned a trip to Italy to stock up.
Nervous about traveling alone, she took a recommendation from one of her husband’s former co-workers and called Cowboys4Angels. The agency sent Starr along for $27,000. She says they kept separate rooms, and she turned down his advances because she was still mourning.
But somewhere in Italy, she told him her husband had left her a lot of money.
Back in New York, she says, she was done with him. But the agency wasn’t.
According to her affidavit, the agency’s owner kept calling to say Starr missed her. A thank-you meeting turned into flattery, and by March 2025 she had paid about $150,000 to keep him exclusive for six months.
By Dec. 1, 2025, Starr had moved into her Upper West Side apartment under an “independent contractor agreement.” It was worth $368,000 for four months, before paying another $90,000 more for April and May, according to The Independent.
Then came the ask that unraveled everything. Starr allegedly said he wanted to be with her alone, but leaving Cowboys4Angels meant buying out his contract for $10 million. Flippo was on gabapentin and codeine after a painful post-surgery infection.
She says she signed his “exit agreement” in February 2026 while drunk and without a lawyer.
JPMorgan Chase flagged the wire as possible fraud and recalled it, and a second bank blocked the transfer too. Instead of stopping, Starr allegedly had her open a joint Charles Schwab account in both their names, where she moved $5.95 million.
He then allegedly pressed for the remaining $4 million. That ended when lawyers she’d hired for unrelated matters confronted him, and she says he grew angry and threatened to leave with her money.
She is now asking the court for the $5.95 million back, legal fees and a restraining order freezing what’s left.
On social media, the report landed somewhere between true crime and prestige TV.
“Wasn’t this an episode of White Lotus?” one person asked under an X post. Another went full daytime courtroom: “People’s Court, voice: after taking $6M dollar from this widow. He is accused of being: a huckster and a fraud: The Widow Taker.”
Others had no sympathy for Flippo. “He dated her for money, and voila, she’s shocked when she finds out he dated her for money,” one person posted. Another pointed to the $4 million that never left her account, writing, “She got off cheap.”
Flippo’s attorney, Larry Hutcher, says Starr has been burning through the money on luxury goods and travel.
Meanwhile, Cowboys4Angels, which isn’t named as a defendant, declined to comment.
The agency has brushed up against headlines before. It reportedly supplied an escort for at least one of Sean “Diddy” Combs’ infamous “freak-offs,” according to PEOPLE.
Flippo’s court papers note that people with her condition have an average life expectancy of 48 to 51. She’s 49, and she’s spending that time trying to get her husband’s money back.
“I now realize I was foolish,” she admits in the filing.
Now a judge will decide whether Starr has to pay for it.