Marianne Flippo paid a male escort roughly $635,000 for eight months of exclusive companionship. Then, according to a lawsuit filed this week in Manhattan Supreme Court, he and his agency allegedly told her the only way to make the arrangement permanent was to pay $10 million to buy him out of his contract.
“I now recognize that I was the victim of a horrendous scheme by Starr who is a sociopath who lacks any conscience,” Flippo said in a sworn affirmation filed with the court.
The suit names the escort as Gregg Starr, an employee of an agency called Cowboys 4 Angels, and describes Marianne as newly widowed, managing money alone for the first time, and living with a rare genetic disorder that heightened her vulnerability to drugs and alcohol. Court documents allege Starr built her trust before defrauding her of nearly $6 million.
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 for a recent surgery. The two ordered shots for the table, and after roughly five drinks, they produced an “Exit Agreement” requiring her to pay $10 million to end Starr’s ties to the agency.
“While I was drunk and confused (all of which was exacerbated by my medications and medical condition), Starr and Collins began to press me to sign the Exit Agreement,” Flippo said in her affirmation. She says 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 independently 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.
A circumstantial meeting
Flippo 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. In December 2024, still grieving the loss of her husband, Chad, and needing to travel to Italy for a medication that had become unavailable in the U.S. because of the war in Ukraine, she asked a former colleague of Chad’s for help finding an Italian-speaking companion.
Chad joined Roblox when it was still a startup—years before it became the multibillion-dollar gaming platform used by tens of millions of children worldwide—earning multiple patents and building what Flippo describes as “a substantial amount of wealth.” Battling with depression, Chad died by suicide in August 2024. The two had been married 28 years, had three children, and were together since they met at 13.
Flippo was referred to Cowboys 4 Angels, which paired her with Starr. At first, she believed the company provided personal assistants but now says she learned it is an escort agency. Despite staying in separate rooms, Starr made advances toward her on the trip, which she turned down, and she paid the agency $27,000 for his assistance, split into three $9,000 payments she now believes were structured to avoid IRS reporting requirements. The agency kept calling afterward and told her Starr missed her. An employee named Bridget Collins became, in Flippo’s account, a trusted confidante who encouraged her to reconnect with him.
By March 2025, Flippo 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. But the agency kept calling, and she eventually agreed to speak with him again. By December 1, 2025, Starr moved into her Upper West Side apartment, and she signed a formal “Independent Contractor Agreement,” paying $368,000 for his companionship through May. The contract states Starr would serve as her “male companion” for an average of 16 days a month; that the arrangement “do[es] not include sexual acts of any kind;” and includes a clause requiring the money be returned if Starr cheated on her with that same ex-girlfriend. In January 2026, she paid another $90,000 to extend the exclusivity period.
Her illness runs through nearly every filing. People with vascular Ehlers-Danlos syndrome have an average life expectancy of 48 to 51 years; Flippo is 49. After surgery in early 2026, she was prescribed gabapentin and codeine, which she says left her “in a compromised mental state” for months, worsened by a severe infection in both arms. It was during this period, her complaint alleges, that Starr and Collins began telling her he needed $10 million to buy his way out of his contract.
“Unfortunately, I was not capable or perceptive enough to know these statements were false but, since I loved and trusted Starr, I relied on what he said. I now realize I was foolish,” Flippo said in her affirmation. And so the $5.95 million was transferred.
Flippo was already a client of Larry Hutcher for unrelated legal matters when Starr’s demand for an additional $4 million came up, according to her affirmation. Hutcher says he looked into what had happened and concluded she “was the victim of a horrific scheme.” She didn’t see it that way, and Hutcher said she was still “under the Svengali-like control of Starr.”
Starr, meanwhile, had retained his own attorney to draw up an agreement for the additional funds, and Hutcher arranged a July 7 meeting at his office to address it. Starr believed the meeting was to negotiate the $4 million; instead, Hutcher confronted him and said “he was shamelessly and criminally exploiting Marianne’s vulnerabilities and had defrauded her out of $5,950,000 and that no further money would be paid.” Starr, according to both affirmations, became visibly angry and threatened to abscond with the $5.95 million already taken if she didn’t pay the rest.
“In my fifty (50) years of practice I have never seen the type of outrageous conduct that exists in this case,” Hutcher said in his affirmation.
