The ins and outs of cheating

When New Yorkers have love affairs, here's who they hire to keep them undercover

Jacquie Boyd/Getty Images

On a brisk day in April, Harry Macklowe, one of the larger personalities among New York’s larger-than-life capitalists, addressed reporters waiting outside a Manhattan civil courtroom. The wisecracking billionaire, known for record-setting real estate plays — such as dropping $1.4 billion on the General Motors Building and developing 432 Park Avenue, North America’s tallest residential tower — left the courtroom facing the loss of more than half of his 

$2 billion fortune to his estranged wife, Linda. Nevertheless, he was in high spirits and joked with reporters on the scene.

“A husband has been giving his wife incredible pleasure, beyond her wildest fantasies, for 30 years of marriage. But they always have sex with the lights off,” Macklowe quipped.

“One night she gets curious and flips the light switch on. She is shocked to see that her husband is using a vibrator on her. ‘I knew it, you jerk, explain the vibrator!’ she says. ‘Explain the kids!’ he says,” Macklowe deadpans.

Only a true master of the universe could face a vicious divorce suit with such levity. Notoriously, Macklowe’s wife never signed a prenup, leaving him financially vulnerable, yet he remained unabashed.

For at least two years, Macklowe, 79, allegedly visited a somewhat younger woman, 62, whom he kept in a luxury apartment building he owns at 737 Park Avenue — a short jaunt from his home in the Plaza Hotel, according to published reports. In July 2016, Linda served him divorce papers after he arrived in London with his girlfriend, who was identified as Patricia Landeau, president of the French Friends of the Israel Museum in Jerusalem.

At least in public, Macklowe appears completely unfazed by the dissolution of his marriage of 58 years. He says he intends to marry Landeau.

While many of the particulars of Macklowe’s case are largely unknown, we do know quite a lot about the proclivities of his likeminded peers.

In all areas of day-to-day life, wealthy New Yorkers rely on a vast service economy, from real estate brokers, attorneys and tech gurus to doormen, drivers and concierges — and their sex lives are no different. LLNYC talked to the professionals wealthy Manhattanites employ in the service of their extracurricular love affairs. What we got was a look behind the moral façade of the stinking rich.

Hunting grounds

Any night of the week, a seat at the King Cole Bar at the St. Regis, Bemelmans Bar at the Carlyle or The Mark Bar at the Mark Hotel buys advanced instruction for the student of infidelity. Disgraced former New York governor Eliot Spitzer, under the nom de guerre “George Fox,” paid women $1,200 for late-morning romps at the Mark, according to award-winning investigative reporter Peter Elkind’s book “Rough Justice: The Rise and Fall of Eliot Spitzer.” Sometimes, in a single day, he would allegedly have three escorts sent one after the other to his room. Working women have never forgotten the Spitzer windfall, and high-priced hookers and their pimps continue to aggressively prowl the Mark’s bar, preying on hotel guests for whom business is also pleasure.

Dating apps have made adultery
even more convenient, but technological illiteracy
also leads to embarrassing exposure.

But while the convenience and discretion of an Uptown hotel may seem like the perfect pleasure palace for extramarital romps, most choose to take their sins further afield, our sources said. That means the denizens of Park Avenue prefer to shake it with their sugar babies Downtown, or even in Brooklyn. Likewise, Downtown’s faster, newly made multimillionaires enjoy the fauxsophistication of wearing the linens thin north of 42nd Street.

Meanwhile, “[closeted] gay men tend to go to Brooklyn, or they go to their office [after hours],” says divorce attorney Nancy Chemtob, who represented Tory Burch, Annette Lauer, Tiki Barber’s ex-wife Ginny Cha, Star Jones, Stephanie Madoff, and Diandra Douglas. Over the years she’s become expert on the sex lives of the rich and famous.

She explains that offices are more popular spots for closeted or bisexual men to rendezvous because two men checking into a hotel still raises more eyebrows than two men walking into an office on Madison Avenue.

But when it comes to public rendezvous, private investigator Herman Weisberg warns that rooftop bars are essential criteria when selecting a love hotel.

Weisberg, a retired NYPD detective who spent a chunk of his 20-year career as a special investigator for Manhattan District Attorney Robert Morgenthau, now makes a living as the head of an investigation firm that specializes in the movements of wealthy cheaters.

“If you are spotted [going into a hotel elevator] you can always tell a spouse, ‘I was at the bar. I wasn’t in a hotel room.’” Weisberg says. “Unless they have their pants inside out, there is no indication of what they were doing. It’s a easy explanation.”

Better still is avoiding public places altogether. City real estate brokers earn a nice living renting and selling small apartments to the mistresses of well-healed clients.

“Sex and real estate are married in so many ways,” says a high-end Manhattan broker who has sold or rented a half-dozen “glorified girlfriend dorm rooms.” He adds that certain brokers traffic in “hot tail for single dudes” and then make their dinero arranging the lease on a love shack.

Jacquie Boyd/Getty Images

“The whole studio and one-bedroom market is subsidized by what I call ‘the mistress economy,’” a real estate developer told Observer columnist Richard Kirshenbaum for a 2016 article. “While the market for larger apartments has stalled, the studio and small one-bedroom market is on fire. Not because of the foreign rich but because younger, better playthings also need a place to live. How could you be a 20-something living in a luxury building in Manhattan instead of in Williamsburg, unless your parents or a sugar daddy were paying for it?”

Major Manhattan landlords are even better positioned for infidelity than the merely rich. When you own hundreds or thousands of units across the city, how easy is it to take just one off the market for your mistress?

But for the rest, the purchase of a property for a mistress involves a fairly complex monetary shuffle and paper trail. If, for instance, a spouse takes a particular interest in the finer points of their marital assets, the jig could be up. It becomes a matter of playing “how to hide $1.5 million” with your accountant-turned-accomplice — a game that may substantially increase next year’s Christmas bonus. You have to figure out how to make a big financial play look mundane.

“People have habits that you can see over time,” Chemtob says. “So if you look at someone’s bank and credit card statements over five years, and you see that every week they take $250 out at the ATM and they spend $20,000 on their American Express, but then, all of the sudden, they start spending $32,000 on the Amex and start taking out $2,000 a week in cash, and nothing else has changed in their life, that is a huge red flag.”

One place wealthy adulterers almost never conduct their affairs is their own homes.

“In eight years of doing this I have only seen three times where people utilized their home and brought their lovers back,” Weisberg says. “Nobody does that. I almost fell off my chair the three times I actually saw that. It turns my stomach. That’s the house your spouse probably helped pay for and now you are in bed with your girlfriend or boyfriend. That is pretty unheard-of. If you are going to get the heebee-jeebees about something, it’s going to be having sex with your lover in your own home.”

And because most prefer to put as much distance between their home and their liaisons as possible, business trips are a favorite way to stray.

“One client thought her husband was cheating. So I hired this guy and he flew to Las Vegas to follow him,” Chemtob says. “The private investigator followed the husband and reported back, ‘He’s not cheating. He is being a good boy. He’s just hanging with the boys.’ Meanwhile he sends me a picture of a completely gay party. My client was right.”

Geography, however, isn’t the only way in which the randy rich attempt to displace their affairs. Class is often every bit as important as place, as high-net-worth people very rarely gravitate to other high-net-worth people for affairs, our sources said.

Both in life and pop culture, there is a long-standing cliché in which a “rich person in crisis gets his or her vitality restored by a brief intimate contact with the full-blooded life of the poor. What lurks behind the compassion for the poor is their vampiric exploitation,” the philosopher Slovaj Zizek writes in “The Pervert’s Guide to Cinema.”

“It’s obvious and probably not necessary for me to mention that money is very intoxicating” for working-class paramours, Weisberg says. And the clear appeal of enjoying a poor student or a struggling actress is the power of money to lure a lover and better facilitate “favorable situations.” Even vanity is no substitute for the sexual thrill of conquering a working class lover.

“I have observed men and women cheating on their spouses with people who, in my opinion, are very much less attractive,” Weisberg says. “I show clients visual proof of the affairs and I have heard comments like, ‘Are you fucking kidding? S/he’s fooling around with that pig?'”

Tech advantage

Social media and dating apps have made adultery even more convenient for Manhattan’s leisure class. But in the same stroke, technological illiteracy also leads to embarrassing exposure.

“As soon as a client comes into my office, I say, ‘Can I see your phone?’” says Chemtob. “A spouse can enable the Find My Friends app on their spouse’s phone without them knowing. So I turn it off right away. People come to my office and say, ‘I called my wife and she says she is with her friends at SoulCycle but Find My Friends showed her at the Four Seasons Hotel on 57th Street — and she wasn’t having lunch!’”

She adds that her wealthy clients were quick to latch onto digital dating services like Ashley Madison, Tinder, Grindr, Match, JDate and even Christian Mingle, leading to a spike in affair-related divorces.

“The biggest way people get busted is on their second iPad,” a Manhattan playboy, who spends half his year abroad, told LLNYC from his phone while lounging poolside in Ibiza. “They leave an iPad at home and a text from some girl pops up while their kid is watching a video.” Now, he says, everyone has learned to encrypt their text messages with services like Telegram. Meanwhile, the less tech-savvy seek work-arounds.

“We once followed a subject [a man] for a long period of time who was very preoccupied with his phone,” Weisberg says. “We never saw him use a burner phone and our client had, as per an agreement between the couple, full access to one another’s devices.”

The situation left Weisberg’s investigators completely puzzled. How was the man continuing to communicate with his woman on the side? Then an investigator sat next to the man in a public place and asked about the Words with Friends game the subject was playing. As they talked, messages popped up, which the man tried to delete.

“The cheaters were communicating via the chat function on Words with Friends, something our client never thought to get access to. It led to total distrust and the end of their marriage.”

Overall, society has adapted astonishingly quickly to new technology. We are accustomed to being watched. We assume there is a spy in our midst. Not only are security cameras everywhere — and accessible to investigators for as little as a $100 bill in the pocket of the right doorman or bellhop — but every passerby is armed with a high-definition camera. It’s forced us to grow up as a culture, to accept that our antics are always available for playback.

But the proliferation of technology has also produced the reciprocal effect of emboldening the unfaithful in specific ways. It’s easier than ever to parley with a stranger from the safety of a screen. So why call a service when you can swipe right? Why skulk in a Downtown bar when you can make an online arrangement? More convenient still, relationship sites have begun importing the kind of clinical negotiation typically seen in the boardroom into the bedroom.

“My friends view sugar daddy sites like Seeking Arrangements as very efficient,” a well-connected Upper East Side mogul said over breakfast at the Odeon in Tribeca. For the uninitiated, Seeking Arrangements is a popular website “where beautiful, successful people fuel mutually beneficial relationships.” It advertises “relationships on your terms.”

Sites like Seeking Arrangements attempt to assuage negative connotations associated with the outright sex trade, shifting the conversation to more palatable considerations: Can it count as prostitution if, instead of leaving money on the dresser, you put the young lady you met online through NYU? Who is using whom if it was her idea? Users say that like Airbnb or Uber, sugar daddy sites are unlocking unused inventory (i.e. people) and ironing out the inefficiencies of sex.

Adultery, meet the sharing economy.

New attitudes

“I think there are two types of people who are ripe for affairs,” says our Upper East Side mogul. “There is the wealthy, unattractive and successful man who has never had a pretty girlfriend. He may have married the first girl that came along, and all the sudden he becomes successful and has a lot of money. Suddenly he realizes that money equals power. Those account for a lot of second marriages.

“On the female side of the equation, I’ve seen the neglected spouse who feels underappreciated. The wife may feel like she is a golf widow or a work widow and is aging and wants to feel like she is still attractive. Then a trainer comes along …”

But increasingly, these affairs are being tolerated by spouses for reasons both libertine and slavish.

“I have a client whose husband started having an affair and was very open about it,” Chemtob says. “He told his wife, and the wife would wake up, and the girlfriend would be in the other bedroom. It was absolutely crazy. They had small kids. He just didn’t care.”

Nevertheless, the wife never left him, choosing to tolerate his infidelity rather than relinquish her lavish lifestyle.

“That woman had a prenuptial agreement where she got hardly any money if she got divorced. He felt like he could do whatever he wanted because she didn’t get any money. I think prenups are almost a license to misbehave. People get trapped in their marriages by their prenup and so they have to turn a blind eye.”

She says husbands who bully their way into a ménage à trois with cash and gifts are another source of trouble.

“I have a lot of threesome issues,” Chemtob says. “There was one where the husband said, ‘I’ll buy you a major piece of jewelry if you let me be single for a week.’ She said okay. He went out with a woman for that week and he ended up marrying her later,” Chemtob says. But another time “the husband wanted a threesome. They had the threesome and the wife ended up falling in love with the other woman.”

But manipulation isn’t the only reason a couple would choose to tolerate occasional hanky-panky. We’re told affairs are commonly sanctioned when a spouse becomes an invalid, or when one partner loses interest in sex.

But increasingly, the continental attitude accounts for spouse-sanctioned trysts.

“In Europe it’s not such a big deal as it is in America,” our poolside playboy said. “You have a much longer leash in Europe than you do in New York.”

“There is a very different European viewpoint,” our Upper East Side mogul added. “I mean the French even have term for it, they call it ‘cinq à sept.’ A man might have a younger girl and go home to his wife afterword. He has his little dalliance and then buys his wife a Birkin bag. It is a little more open.”

And it’s easy to see how the European perspective on adultery could enter the collective consciousness of the rich and powerful in a globalized world, where a cosmopolitan life is the ultimate status symbol. When you spend your springs in Provence, your summers in Capri and your winters in Gstaad — and a Central Park-adjacent aerie somewhere in between — you get used to dealing with cultures where it is not considered as shocking to have a relationship outside of marriage.

These days, our man on the Upper East Side says, “you have to make a distinction between someone who is having an affair and someone having recreational sex. There is a big difference between an emotional affair and somebody going to Vegas and getting a blowjob. If the wife finds out about that, I don’t think they are going to get a divorce. Some couples don’t look at it as a deal breaker as long as the wife isn’t embarrassed.”

But while attitudes may be slowly shifting toward tolerance — or perhaps an ability to stare the human condition coldly in the eye — one thing hasn’t changed: the veil of secrecy.

Once you start asking about adultery, it’s next to impossible to meet an adulterer. Throughout dozens of interviews conducted within the comfortable territory of the hyper-privileged — cocktail parties in a Tribeca penthouse, lunch at Le Bernardin, evenings at Doubles and charity galas along Central Park — infidelity was always displaced. It’s always the other man or the other woman. Always a friend, or a friend of a friend. Always, “I knew a guy who did you won’t believe what.” But once you’ve stopped insisting upon adultery and start listening, you start hearing things.

You start to hear about “absolutely scandalous” trips to Marrakech, where everyone’s boyfriend has a boyfriend, and where the boys are so young and so “well-groomed.” You catch young wives discussing their paramours on the Montauk-bound Long Island Rail Road car. At the Rose Club in the Plaza Hotel, the lascivious braggadocio of boardroom-worn men is broadcast at top volume over martinis.

Despite changes both social and technological, infidelity remains as it was for our parents and grandparents, stuck in the past, as an open secret.

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  • Kaitlin O’Leary

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