Exclusive: Widow of late Roblox mogul says male escort fleeced her for $6 million during ‘lowest period of her life’

Exclusive: Widow of late Roblox mogul says male escort fleeced her for $6 million during ‘lowest period of her life’ Marianne Flippo is taking West Point graduate and onetime ‘companion’ Greggory Starr to court in an attempt to get her money back - Bookmark The grieving widow of an early Roblox employee who died by suicide in 2024 says a male escort she met in the aftermath was in fact a scheming con artist who pilfered $6 million of the fortune she inherited from her late husband – and was on the cusp of extracting another $4 million from her when the alleged scheme finally came undone, according to a tranche of lawsuit-related documents obtained by The Independent. To the very end, Marianne Flippo was convinced that Greggory Blaine Starr “loved her,” and she trusted his “misrepresentations,” reads a complaint filed September 14 in Manhattan Supreme Court. “Marianne believed she was helping her new love and has only recently realized that Starr is a fraudster who shamelessly exploited her during the lowest period of her life,” the complaint states. At the time Starr launched his “ruthless plan,” Marianne was not only grieving the loss of her partner of nearly three decades, she was also recovering from surgery, dealing with a severe infection and under the influence of various prescription medications, including an opioid, according to the complaint. It took some time for Marianne to recognize what was happening, since she was “in essence, suffering from ‘Stockholm syndrome’ and was under the Svengali-like control of Starr,” another one of the filings contends. In her own affidavit, Marianne concedes, “I now recognize that I was the victim of a horrendous scheme by Starr who is a sociopath who lacks any conscience.” She is seeking, among other things, a temporary restraining order barring Starr from spending any more of her money, which a companion filing says he is “depleting… rapidly on luxury goods and travel.” Reached by phone on Tuesday, Starr, a West Point graduate whose Instagram shows he is currently visiting Dubai, told The Independent he had been unaware of Flippo’s suit, and, sounding flustered, quickly ended the conversation. Attorney Larry Hutcher, who is representing Marianne, said that suing Starr is “the only way she’ll be able to get her dignity back.” “She obviously feels exploited and it took a lot of courage for her to bring this proceeding,” Hutcher told The Independent. “But she really was screwed over, and she’s trying to make herself whole.” Marianne Taylor began dating Chad Flippo in 1990, when the two were 13 years old, her affidavit begins. The pair got married in 1996, the same year Chad’s mother was murdered by his father, a minister in West Virgina. Together, the Flippos raised three kids. “Chad and I were married for 28 years when [on August 5, 2024] he unexpectedly succumbed to depression and took his life,” Marianne says in the affidavit. “My life dramatically changed in an instant.” Chad, a programmer with multiple patents to his name, had joined Roblox, the online games platform, as a start-up, and had accumulated what Marianne describes as “a substantial amount of wealth,” that she later inherited. During Chad’s life, he managed the couple’s financial affairs and she had no experience managing money, according to the affidavit. On top of it all, Marianne has suffered all her life from vascular Ehler-Danlos syndrome, a rare genetic disorder that renders organs and blood vessels brittle and susceptible to tearing, the affidavit continues. Aside from chronic pain, weakness and exhaustion, it says Marianne must also deal with blood clots and inflammation that cause her ongoing confusion and anxiety. “Individuals with vascular Ehler-Danlos have an average life expectancy of 48-51 years,” according to the complaint filed in the case. “Marianne is currently 49 years old.” One of the few medications Marianne is able to tolerate is manufactured in Russia and became unavailable in the U.S. after the invasion of Ukraine, the affidavit explains. However, it remains available in Italy, so in December 2024, Marianne decided to travel there and stock up. Nervous about traveling alone, Marianne asked one of Chad’s former coworkers for suggestions, the affidavit goes on. It says they recommended she contact Cowboys4Angels, which could pair her up with someone who spoke Italian. Cowboys4Angels provides “straight male companions” at prices ranging from $750 (two hours) to $22,000 (full week), and reportedly provided a male escort for at least one of Sean “Diddy” Combs’s infamous “freak-offs.” Its website promises clients “the ultimate boyfriend experience.” Marianne claims she did not realize at the time that Cowboys4Angels was in fact an escort service. (She soon became well aware, her affidavit says.) Cowboys4Angels connected Marianne with the 38-year-old Starr, who served in Europe for a period while in the Army, charging a total of $27,000 for him to go to Italy with her. The two stayed in separate hotel rooms, although Starr “did make physical advances,” according to the affidavit, though Marianne says she “turned him down because I was still in mourning and not interested in any sort of romantic relationship.” Yet, Marianne felt herself beginning to form a bond with Starr, sharing “personal details and confidences” with him, including the fact that she “had been left a substantial amount of money by my deceased husband,” the affidavit says. When the two got back to New York, Marianne resumed her normal life and had no intention of including Starr in it, the affidavit maintains. But, it claims, the owner of Cowboys4Angels and her assistant started calling regularly, telling a lonely and vulnerable Marianne that Starr missed her and wanted to see her. Flattered but confused, Marianne eventually agreed to get together with Starr “just to thank him for his assistance on the trip,” the affidavit states. “When I met with Starr, he showered me with praise and affection,” it says. “With all of the craziness in my life, the attention and affection felt good.” Soon, Starr told Marianne that he wanted to date her exclusively, which the Cowboys4Angels owner said would be “expensive,” according to the affidavit, In March 2025, Marianne says she paid Cowboys4Angels about $150,000 to have Starr all to herself for the next six months. Throughout this time, Starr convinced Marianne that he loved her, and she in turn found herself falling for him, the affidavit states. But by August 2025, Marianne had become convinced that Starr was cheating on her with an ex-girlfriend, and broke things off with him a month or two later, the affidavit says. The owner of Cowboys4Angels subsequently contacted Marianne, pleading with her to give Starr a chance to explain himself. She reluctantly agreed, according to the affidavit. “When I spoke to Starr, he apologized profusely for seeing his ex-girlfriend and eventually I agreed to get back together with him,” Marianne says in the affidavit. “On December 1, 2025, Starr moved into my Upper West Side apartment. Back under his spell, Starr convinced me to sign an ‘Independent Contractor Agreement’ for the months of December 2025 through March 2026 for him to continue seeing me.” Those four months would cost $368,000, plus another $90,000 to secure Starr exclusively for April and May 2026. In the meantime, Marianne developed a painful infection in both arms following a surgical procedure, and was prescribed gabapentin, codeine, and other powerful drugs, the affidavit states. Between the various medications, which have increased effects on Marianne due to her vascular Ehler-Danlos, and the “emotional rollercoaster” she had been on since Chad’s death, her affidavit says she was “not in my right mind.” So, when Starr told Marianne that he wanted to be with her and her only, but that he could only leave Cowboys4Angels by buying out his existing contracts at a combined price of $10 million, she agreed. “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,” the affidavit asserts. “I now realize I was foolish.” Marianne signed Starr’s “exit agreement” in February 2026, while drunk and high on painkillers, and without an attorney’s review, according to the affidavit. But when Marianne tried to wire the $10 million to Cowboys4Angels’ bank account, the fraud department at JPMorgan Chase became concerned and recalled the funds, the affidavit says. Starr then “implored” Marianne to use a different bank to send the money, which she attempted to do, before that transaction was also blocked due to the bank’s apprehension over potential “fraud and coercion.” “Still under Starr’s spell and continuing to believe his misrepresentations, I failed to heed these warning signs,” the affidavit states. “In his never-ending and increasingly desperate effort to secure the funds, Starr directed me to open a joint account at Charles Schwab under both our names. This would allow Starr access to the money without triggering the bank’s concerns about fraud.” Once the money was there, Starr said he would withdraw the funds to terminate his Cowboys4Angels contract and focus on their future together. So, Marianne made a series of transfers into the Schwab account, totaling $5.95 million, according to the affidavit. It says Starr then began pressing Marianne to deposit the additional $4 million, even retaining an attorney to draw up an official agreement. At the same time, Marianne had hired lawyers of her own, to help her with legal issues unrelated to Starr, but who became suspicious when she mentioned the $10 million she was giving him, the affidavit states. They called a meeting and confronted Starr, who became “visibly angry,” allegedly threatening to leave Marianne and take her money with him. “Up until this point, I had believed Starr’s lies,” Marianne’s affidavit says. For his part, Hutcher submitted an affirmation that states, “In my fifty years of practice I have never seen the type of outrageous conduct that exists in this case.” Marianne Flippo is now seeking the return of the $5.95 million, plus an order preventing Starr from spending any more of her money in the meantime, as well as attorneys’ fees and court costs. A person who responded to a text message at Cowboys4Angels, which is not named as a defendant in the case, declined to comment.