Widow of Roblox pioneer drained $5.95M in escort contract scheme

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 told her the only way to make the arrangement permanent was to pay $10 million to buy him out of his contract. She transferred $5.95 million into a joint Charles Schwab account, which the escort, Gregg Starr, drained to $12.61 within weeks, according to bank records filed with the court. The case alleges a horrendous scheme that exploited her grief and a rare genetic disorder.

Starr, an employee of an agency called Cowboys 4 Angels, allegedly built Flippo's trust before defrauding her, court documents state. Flippo, newly widowed and managing money alone for the first time, lives with vascular Ehlers-Danlos syndrome, a rare disorder that makes her blood vessels and organs prone to tearing and leaves her unusually sensitive to alcohol and medication. In her sworn affirmation, she said, "I now recognize that I was the victim of a horrendous scheme by Starr who is a sociopath who lacks any conscience." The lawsuit describes how Starr and agency employee Bridget Collins pressured her to sign an "Exit Agreement" while she was drunk and confused during a February 2026 trip to visit Starr's mother.

Flippo's husband, 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. He earned multiple patents and built "a substantial amount of wealth," Flippo said. Battling depression, Chad died by suicide in August 2024 after 28 years of marriage, leaving three children. In December 2024, still grieving and needing to travel to Italy for medication unavailable in the U.S. because of the war in Ukraine, Flippo asked a former colleague of Chad's for help finding an Italian-speaking companion. She was referred to Cowboys 4 Angels, which she initially believed provided personal assistants but now says was an escort agency.

Flippo paid the agency $27,000 for Starr's assistance on that trip, split into three $9,000 payments she now believes were structured to avoid IRS reporting requirements. The agency kept calling afterward, and by March 2025, she agreed to pay roughly $150,000 for Starr to be "exclusive" with her. She broke up with him that October after learning he was seeing an ex-girlfriend, but the agency encouraged her to reconnect. 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 stated Starr would serve as her "male companion" for an average of 16 days a month, explicitly excluded sexual acts, and required money to be returned if Starr cheated 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 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. Her first two attempts to wire $10 million were flagged as suspected fraud by JPMorgan Chase and Westpac, so Starr directed her to open a joint account at Charles Schwab, which she says let him access funds without triggering a bank's fraud review.

Larry Hutcher, Flippo's attorney, confronted Starr at a July 7 meeting after Starr demanded an additional $4 million. Hutcher said he told Starr 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 became visibly angry and threatened to abscond with the money already taken. "In my fifty (50) years of practice I have never seen the type of outrageous conduct that exists in this case," Hutcher said. Flippo was already a client of Hutcher for unrelated legal matters, and he concluded she "was the victim of a horrific scheme," though she didn't see it that way, remaining under "the Svengali-like control of Starr."

This case is a stark reminder that fraudsters target emotional vulnerability, not just financial naivete. Joint accounts can bypass fraud detection systems that would otherwise flag large, unusual transfers. For executives and wealthy individuals, the lesson is clear: financial decisions made during grief or medical vulnerability require independent oversight. Family offices and wealth managers should implement procedures to verify large transfers with a trusted advisor, especially when a client is newly widowed or managing money alone for the first time.

The lawsuit also raises questions about the regulatory gray area around "companionship" contracts that explicitly exclude sexual acts but function as exclusive arrangements. As these services become more mainstream, the absence of clear rules creates opportunities for exploitation. For boards and leaders, this case underscores the importance of robust financial controls and the need to protect beneficiaries who may be in a compromised state. The $5.95 million loss is a cautionary tale that even sophisticated families can be victimized when safeguards are missing.