NYC Widow Sues Male Escort, Claiming $6 Million Scam

A wealthy New York City widow is suing a male escort, claiming he scammed her out of $6 million through manipulation and false declarations of love. Marianne Flippo, 49, alleges that Gregg Starr, 38, convinced her to pay him $10 million to escape his contract with an escort agency.

Flippo, the widow of Chad Flippo, a creator of software for the online game "Roblox," contends that Starr, whom she met through the escort agency Cowboys 4 Angels, exerted "Svengali-like control" over her. She claims Starr declared his love and stated that the only way they could be together was if she paid off 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," Flippo stated in court documents. "I now realize I was foolish."

Flippo, who suffers from a serious genetic medical condition, met Starr a few months after her husband's death in August 2024. She initially hired Starr for $27,000 to accompany her on a trip to Italy for medication. According to the lawsuit, she did not realize Cowboys 4 Angels was an escort agency. The pair continued their relationship, and Starr eventually moved into Flippo's New York apartment in December. Flippo claims she paid over $450,000 to keep him "exclusive."

The situation escalated during a trip to Atlanta earlier this year. Flippo alleges that while she was on strong medication following surgery, Starr and another escort service worker coerced her into signing a $10 million "Exit Agreement" to buy Starr out of his contract. She recounts being plied with alcohol in a hotel room until she signed the agreement.

When Flippo attempted to wire the $10 million, her bank flagged the transaction for fraud. Despite this, she continued with the transfers, eventually moving $5.95 million into a joint account with Starr. Her attorney, Larry Hutcher, discovered the alleged scheme when he reviewed the "Exit Agreement" in June, describing it as unbelievable.

"I looked at this and said, ‘Not even close. This doesn’t pass any smell test by any stretch of the imagination,'" Hutcher said. He confronted Starr, calling him "nothing more than a common criminal."

According to the lawsuit, Starr then threatened to hide the money unless Flippo paid the remaining $4 million, at which point she realized she had been scammed. The suit alleges that Starr has since transferred $5.7 million out of the joint account into one under his sole control.

Starr, however, denies the allegations. He told The Post that much of the $6 million was spent on joint expenses and charitable donations, and that approximately $3 million remains. He claimed the "Exit Agreement" was Flippo's idea and that he did not want it. Starr's attorney, Todd Spodek, stated, "The complaint tells a dramatic story; the evidence will tell the actual one."

Cowboys 4 Angels was not named as a defendant in the lawsuit, but Hutcher indicated that this could change as the investigation continues.

"This lawsuit is simply about Marianne recovering her dignity and her sense of self," Hutcher added.