Gregg Starr

Introduction

Gregg Starr is a 38-year-old New York City male escort who worked through Cowboys 4 Angels, a “straight elite male companions for women” agency featured on the Showtime reality 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 through what her lawyer calls a “sinister fraud.” The plaintiff, Marianne Flippo, 49, is the widow of Chad Flippo, a programmer who created and patented key software for Roblox and amassed a substantial fortune before his 2024 death. Starr denies any fraud, says the money went largely to shared expenses and charitable donations, and insists the relationship’s collapse is being rewritten by litigation.

Background Information

Starr built his companion profile with Cowboys 4 Angels, the high-end “straight elite” agency, while cultivating a lifestyle-brand image: the silver-haired model walked the runway in the Emerald Swimwear show at NY Swim Week in July 2024 and posted regularly to an Instagram account under his own name. Per the court filings described in media coverage, his clients included Marianne Flippo, who hired him in late 2024 for a $27,000 trip to Italy, where she needed to obtain medication that had grown scarce in the United States because of the Russia-Ukraine war. Flippo had been widowed only months earlier: her husband Chad, her sweetheart since she was 13 and her husband of 28 years, died by suicide on August 5, 2024.

The Controversy or Incident That Led to Their Cancellation

Allegations. Everything described in this section comes from a civil complaint and related filings in Manhattan Supreme Court — not from any criminal proceeding or adjudicated finding. Starr has not been charged with a crime and denies the claims; his attorney says “the evidence will tell the actual one.”

Flippo’s complaint alleges that what began as a paid companionship arrangement became a years-long financial scheme. After the Italy trip, the two kept seeing each other, and by December 2025 Starr had moved into Flippo’s New York apartment while, the suit claims, persuading her to pay more than $450,000 to keep him “exclusive.” The relationship’s turning point, per the filing, came during an early-2026 trip to Atlanta, when Flippo was recovering from surgery and on strong medication: she alleges 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 Starr out of his agency contract.

When she tried to wire the full $10 million, her bank recalled the transfer over fraud concerns, according to the suit; she alleges she was then persuaded to open a joint account with Starr, into which she transferred $5.95 million. The arrangement unraveled in June 2026, the filing states, when Flippo retained attorney Larry Hutcher of Davidoff Hutcher & Citron to negotiate the remainder of the Exit Agreement; Hutcher said “This doesn’t pass any smell test by any stretch of the imagination.” At a subsequent meeting, Hutcher told Starr he was “nothing more than a common criminal,” and an incensed Starr allegedly threatened to remove and hide the $5.95 million unless Flippo paid the remaining $4 million. The suit further alleges Starr has moved $5.7 million out of the joint account into one under his sole control and is “rapidly spending” the money — prompting Hutcher to ask a judge to intervene to stop him from dissipating the funds.

Starr tells a different story. Reached by The Post, he said much of the $6 million went to shared expenses and charitable donations, with roughly $3 million left. He called the coercion allegations “not true at all,” insisted the Exit Agreement was Flippo’s idea and one he did not want, claimed she was abusive toward him, and described the relationship as “a wild f—king ride.” His attorney, Todd Spodek, said in a statement: “You cannot rewrite an entire relationship simply by filing a lawsuit after it ends. The complaint tells a dramatic story; the evidence will tell the actual one.”

Public Reaction and Consequences

Allegations. The claims in this section arise from pending civil litigation; no court has ruled on them, and Starr denies wrongdoing.

The lawsuit, first reported by the New York Post on September 16, 2026, spread quickly through news aggregators and social media, where it drew wide attention. The Cowboys 4 Angels agency — reportedly linked to Sean “Diddy” Combs’s alleged “freak-offs” in separate litigation — did not return the Post’s request for comment; it is not currently a defendant, though Hutcher told the Post that could change as he traces what money was paid to it. Flippo’s own filings mix accusation with self-reproach: in an affirmation she called herself the victim of “a horrendous scheme by Starr who is a sociopath who lacks any conscience,” having written earlier that she “was not capable or perceptive enough” to see his statements as false. Hutcher framed the case as “simply about Marianne recovering her dignity and her sense of self.”

Current Status

The case is pending in Manhattan Supreme Court, where Flippo sued Starr on Monday, September 14, 2026, seeking recovery of the roughly $6 million she says she transferred to him and judicial intervention to freeze or recover the funds allegedly moved to his sole-control account. No criminal charges have been reported against Starr, and no court has yet ruled on the complaint. Starr remains publicly defiant: he says he wanted to leave the agency and pursue a real relationship with Flippo “because I was in love with her despite all the other things,” and his lawyer’s statement promises the evidence will contradict the complaint’s “dramatic story.”

Impact on Their Career/Life

Whatever the outcome, the exposure has dismantled the polished image Starr had built: the lawsuit’s coverage put his escort work, the $27,000 Italy booking, and the alleged $10 million Exit Agreement into wide circulation, alongside runway photos and Instagram posts from the lifestyle he was marketing. His Cowboys 4 Angels affiliation is now part of the public record of the case, and the agency’s possible addition as a defendant — and the Diddy-adjacent scrutiny that comes with any association with it — hangs over the proceedings. For Flippo, the litigation is a reckoning with a grieving-period decision she now describes as the result of fraud; her lawyer says the case is about restoring her dignity as much as her money, and the $5.7 million allegedly already moved by Starr sits at the center of the fight.