Gregg Starr

Introduction

Greggory Blaine Starr is a 38-year-old New York City male escort who worked through Cowboys 4 Angels, an agency providing “straight elite male companions for women” that was featured on the Showtime series “Gigolos,” and who is now the defendant in a Manhattan Supreme Court lawsuit accusing him of manipulating a grieving widow out of nearly $6 million. His client was Marianne Flippo, 49, widow of Chad Flippo, an early Roblox programmer who created and patented key software for the game and amassed a substantial fortune before his 2024 death. Starr denies any fraud, says the money went to shared expenses and charity, and — after her attorney said on October 1, 2026 that he had wired more than $1 million to Dubai and “fled” there — insists he is simply traveling. The claims are civil allegations and have never been adjudicated.

Background Information

Starr built a polished lifestyle brand around his escort work: silver-haired and heavily muscled, he walked the runway in the Emerald Swimwear show at NY Swim Week in July 2024 and posted under his own name on Instagram, where he presents himself as a “healthcare private equity investor.” The Independent reported he is a West Point graduate who earned a law degree but, per a source, never passed the bar. Flippo hired him through Cowboys 4 Angels in late 2024, a few months after her husband’s death — Chad Flippo, her sweetheart since she was 13 and her husband of 28 years, died by suicide on August 5, 2024 after a long battle with depression. Living with vascular Ehlers-Danlos syndrome, a disorder that makes the body’s connective tissues and organs extremely fragile and carries an average life expectancy she has already reached, Flippo wanted a companion for a trip to Italy to obtain medication that had grown scarce because of the Russia-Ukraine war; per the complaint, she was told Starr was a military and combat veteran who “also did assassin training — and he knew how to fight,” and she paid him $27,000 for the Italy trip.

The Controversy or Incident That Led to Their Cancellation

Allegations. The claims in this section are allegations from a civil complaint Marianne Flippo filed September 14, 2026 in Manhattan Supreme Court and from her sworn filings in the case. They were never admitted by Starr, he has never been criminally charged, and nothing has been adjudicated in court. Starr denies coercing Flippo, describes the relationship as mutual and loving, and says the money went to shared expenses, household costs and charitable donations.

Per the complaint, the paid trip became a relationship: Flippo paid roughly $635,000 for eight months of exclusivity and more than $450,000 beyond that to keep him exclusive, by December 2025 Starr had moved into her New York apartment, and she alleges that on an early-2026 trip to Atlanta — while she was recovering from surgery and on strong medication — Starr and a Cowboys 4 Angels handler plied her with shots of alcohol and cornered her in a Four Seasons hotel room until she signed a $10 million “Exit Agreement” to buy him out of his agency contract, presented as the only way they could be together. When she tried to wire the full $10 million, her bank recalled the transfer over fraud concerns; she alleges she was then persuaded to open a joint account with Starr and deposited $5.95 million into it, which he moved — $5.7 million — into an account under his sole control, and that the two men warned the money could be concealed unless she paid another $4 million. At a meeting where her attorney Larry Hutcher called him “nothing more than a common criminal,” Starr allegedly threatened to remove and hide the $5.95 million unless the remaining $4 million was paid.

Flippo’s sworn filings describe “Stockholm syndrome” and “Svengali-like control,” and she wrote in an affirmation that “I now recognize that I was the victim of a horrendous scheme by Starr who is a sociopath who lacks any conscience”; The Independent reported she was on the cusp of handing over another $4 million when the alleged scheme came apart. Starr tells the opposite story under oath: the pair were in a domestic partnership with plans to wed — “I loved her,” he wrote, saying Flippo had said she would marry him “without a prenup even though her children would freak out” — and he admits spending much of the money but says it went to Flippo and to charity. He has accused her of treating him like a “human punching bag,” claims she erupted in violent outbursts and sexually abused him, and says she bragged she “typically gets what I want because I have money.” She rejects that account: “I’m 120 pounds,” Flippo told The Post. “I was married to one man for 28 years… I can tell you that I’m not abusive… but unfortunately I can’t prove that to you.”

Public Reaction and Consequences

Contested claims at a hearing. The dueling accounts in this section come from an October 1, 2026 hearing in the same civil case as reported by the New York Post: Flippo’s allegations remain unadmitted, uncharged and unadjudicated, Starr disputes all of them, and the only ruling described — keeping an asset freeze in place — is a provisional order, not a finding against him.

The lawsuit, first reported by the New York Post on September 16, 2026, spread rapidly through aggregators and social media, drawing the kind of attention rarely given to civil fraud suits — the tale of a tech widow, a gigolo and $6 million ran everywhere from Fortune to British tabloids, alongside Starr’s runway photos. At the October 1 hearing on Flippo’s asset-freeze request, Hutcher said bank records show Starr wired over $1 million to an account in Dubai days after she sued: “He moved the money to Dubai, he fled to Dubai… He’s still in Dubai. He’s not coming back.” Starr’s attorney Todd Spodek countered that there was nothing improper — “What’s anyone doing in Dubai? Traveling and enjoying the Middle East” — and noted, per Hoodline, that Starr says his accounts are already frozen and he is living off credit cards. Justice Lyle E. Frank kept the emergency freeze in place, remarking that it was “odd” to transfer money to a “Middle East country” and that “this isn’t like transferring money to Hoboken.” Hutcher accused Starr of playing “a con” on both Flippo and the court, calling his claims the “quintessential definition of chutzpah.”

Current Status

The lawsuit is pending in Manhattan Supreme Court before Justice Lyle E. Frank, with an emergency freeze on Starr’s accounts kept in place as of October 1, 2026. This remains a civil dispute: no criminal charges against Starr have been reported by any outlet covering the case, and none of Flippo’s allegations have been tested at trial. Flippo seeks the return of roughly $6 million; Cowboys 4 Angels is not currently a defendant, though her lawyer has said the agency could be added later as he traces what it was paid. Starr maintains he is simply traveling in the Middle East; The Independent reported that when reached by phone in September he said he had been unaware of the suit before ending the conversation, and his filings concede much of the money is spent, with his side saying about $3 million remained.

Impact on Their Career/Life

Whatever the case’s outcome, the exposure has dismantled the image Starr marketed: the West Point graduate’s runway appearances, Instagram persona and “healthcare private equity investor” branding now share every search result with allegations he is a con man who targeted a grieving, ill widow, and the Cowboys 4 Angels agency — which outside litigation has been linked to Sean “Diddy” Combs’s alleged “freak-offs” — faces possible addition as a defendant. His reported move to Dubai with over $1 million wired abroad makes recovering the money uncertain even if Flippo prevails. For Flippo, who her lawyer says is seeking her “dignity back” as much as her money, the suit is a reckoning with decisions made at the lowest period of her life; for Starr, the identity he sold — veteran, model, companion to the wealthy — has been permanently replaced in public view by the words of her filings: “sociopath who lacks any conscience.”

Sources

• New York Post, “Male escort who allegedly swindled NYC ‘Roblox’ widow out of $6M ‘fled to Dubai’: lawyer,” October 1, 2026 — source
• New York Post, “Wealthy NYC ‘Roblox’ widow claims male escort scammed her out of $6M: ‘Svengali-like control’,” September 16, 2026 — source
• The Independent, “Widow of late Roblox mogul says male escort fleeced her for $6 million,” September 16, 2026 — source
• Fortune, “‘I now realize I was foolish’: Widow of early Roblox programmer allegedly defrauded out of $6 million trying to buy out a man from his escort contract,” September 18, 2026 — source
• Hoodline, “Manhattan Court Dispute Centers on Nearly $6 Million in Transfers Between Former Companions,” September 17, 2026 — source