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Money can buy a lot of things but love has never been one of them, and a cushion of cash doesn’t come with a side order of common sense.
Hustlers can sense a fat wallet from miles away and the ultra-slick are always ready to help the ultra-rich part with their dollars.
The latest alleged example came this week in a lawsuit from widow Marianne Flippo, who is hauling ice-blonde escort Gregg Starr to court, claiming he ripped her off to the tune of $6 million.
Gigolo Starr, 38, worked for the Cowboys4Angels escort service, and was hired by Flippo for companionship after the death of her husband Chad Flippo, a software developer who helped create Roblox but died by suicide in 2024.
Her lawsuit claims Starr — who underwent extensive plastic surgery to achieve what has been described as his “Maxoris” icy stare and sculpted abs — manipulated her by declaring his love, then telling her the only way they could be together was for her to buy out his $10 million contract.
The complaint alleges Flippo, 49, was plied with alcohol in a Four Seasons Hotel room, while “under the influence of multiple prescription medications,” when she then signed millions over to Starr.
Starr has claimed allegations of coercion are “not true at all” and his attorneys, Todd Spodek and Jeremy Feigenbaum, told The Post, “The allegations may be salacious, but two consenting adults are free to conduct a private relationship on terms they both agreed to.
“We have extensive written, audio and video evidence that supports the legitimacy of the relationship and tells a very different story.”
The full truth will be revealed in court, but Flippo displayed all the hallmarks of a person ripe for taking advantage of, an expert explained to The Post.
“[Hustlers] look for somebody who has psychological need and vulnerabilities,” psychiatrist Dr. David Puder told The Post. “If you have enough money, you have a target on your back. And the more money, the bigger the target. Then, if you’re naïve and you have a lot of money, you are very susceptible. And by naïve, I mean that you’ve just never been burned before.”
Such situations frequently arise when people are at their most fragile.
“The things that make someone a good partner also make them susceptible to a romance scam: empathy, loyalty, the capacity to attach.”
Then, he added, “These are all weaponized by the wrong person, who has the dark tetrad: Narcissism, psychopathy, Machiavellianism and sadism.”
Such narcissists are more common than people realize, and every bit as ruthless as you’d expect.
Describing a rogue romantic who prowls the western United States, Alexis Henderson told The Post: “He’ll prey on weak women, usually who work in tech and are nearing their breaking points of frustration with relationships.
“This guy is relatively good looking, but his personality is so engaging that he really makes the women feel special. They’ll go to a bar, he’ll engage a table full of strangers and put the woman at the center of the whole thing.”
The cad is a professional, with seducing women his life’s work, Henderson said.
“Early on his in his life, this man decided that he never wanted to work for a living. He devoted himself to living off women and recognized the kinds of women who would be susceptible to him. They fly him around the country, put him up in expensive hotels. They tend to be bright, lonely and well off.”
Usually, he’ll suggest getting a dog, as that creates an atmosphere of domesticity and makes it harder for the woman to split. “This is very targeted,” said Henderson. “He’s incredibly intentional, very intelligent and knows how to play the psychological game.”
“One person gave him half of a lake house. He gets actual cash and, when he can, he convinces the woman that he knows about stock trading. Then he gets her to open an account. Of course, it’s all in his name.”
The hustler’s relationships last anywhere from a couple months to a couple years, before he moves on according to Henderson.
Puder adds such characters also use love bombing as a tactic.
“It’s normal to idealize someone early on in a relationship, but when the idealization becomes very intense early on, it can feel like the relationship is a once-in-a-lifetime opportunity.
“Sometimes, under those circumstances, all of our attachment systems rev up. Oxytocin and dopamine are all there, and the skeptical side of the brain, the frontal lobe, slows down.”
Even billionaires who have been shrewd, judicious and tough negotiators in their professional lives have ended up embroiled in messy legal cases against lovers who raised eyebrows among their social set.
Entertainment mogul David Geffen, 83, is estimated to be worth $9 billion but became mired in a messy divorce with Donavan Michaels (whose real name is David Armstrong). Armstrong separately brought a breach of contract lawsuit against his ex-spouse following their 2025 split, in which he claimed their first meeting was a tryst for which Geffen paid him $10,000.
In legal documents, Armstrong alleged Geffen demanded an extreme sex life, one in which he “gained satisfaction from causing pain” and sought “total dominion” over Armstrong, who is 50 years his junior. Geffen’s attorneys accused ex-porn star Armstrong of exploiting his husband of less than two years’ generosity, with wild shopping sprees, lavish trips and OnlyFans subscriptions.
The two men settled both cases, with the terms of their agreements not made public. Incredibly, despite the gap between them in net worth, they didn’t have a prenup.
According to Armstrong, despite some mudslinging in court, things ended on a congenial note — and they even reunited on Geffen’s yacht. “David and I are still good friends to this day,” he told The Post, noting he is now pursuing an acting career. “He’s done a lot of great things in my life. There is real love in this world.”
In another case, California-based billionaire businessman Stephen Cloobeck, 64, got involved with Adva Lavie, 29, a former Penthouse Pet who had already been criminally charged with allegedly romance-scamming wealthy men before she met him.
Israeli native Lavie — also known as Mia Ventura, and a prominent OnlyFans star – has pleaded not guilty to felony counts of grand theft, burglary and unauthorized use of personal identifying information.
Cloobeck maintained for a long time he knew Lavie better than anyone and was helping her fight her case. The two were even scheduled to be married in Israel, until a judge denied her permission to leave the US.
Lavie’s bail was revoked after she ditched her ankle monitor, and while in custody authorities have said they have further potential cases involving her in Hermosa Beach, Nevada, Florida, Italy and France. She is currently awaiting trial.
Meanwhile, cops are investigating whether she had also been drugging Cloobeck with ketamine.
Still, despite all that, a person close to the pair told The Post Cloobeck remained friendly with his former fiancée and “still cares about Adva.”
Such behavior is not uncommon according to Puder, who said he often sees people “going back, even after they believe they had been taken advantage of.”
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