Too Rich for Money: Power-Mooching Among the Beau Monde

They’re amply moneyed but never reach for the check—meet the celebrities, socialites and playboys who have turned freeloading into an art form

too rich to pay
Illustration by Neil Webb

I always tell my children life isn’t necessarily fair. That said, there’s unfair and then there’s unfair and slightly ridiculous.

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It was six o’clock and 6 degrees, and I decided to take refuge at the Jay Kos store on Mott Street, one of New York’s coolest and best curated menswear experiences. Jay hosts an informal daily salon; and one never knows who will also be sipping whiskey on the deco sofa viewing the stock of $35,000 alligator jeans.

As the arctic tundra blew me through the front door, I was introduced to Style Man, one of Jay’s besties and one of the visionary fashion talents to the entertainment community. I was immediately taken with his beard; vintage ’80s polo knit sweater, thick-cuffed Polo jeans, combat boots, and couture Chanel goggles. Macallan single malt is a wonderful icebreaker on a frigid Friday, and we chatted about one of his most famous clients.

“The brands just line up to give him everything, Style Man said of the dashing mega-superstar. “He has whole rooms filled with luxury goods. He pays for nothing. The brands will do anything and give him everything, hoping he’ll wear their clothes. He has miles and miles of the latest accessories, jewelry, sunglasses, racks of clothes, all just sitting there.”

I have the privilege of paying full freight for seemingly everyone and everything. When one runs an ad agency, it’s practically a reflex to pull out the wallet. I so often reach for the bill that it’s become automatic muscle memory.

“I made him three velvet tuxedos,” Jay said, fingering his diamond-monkey rapper-style necklace. “And then he just decided to wear a T-shirt and jeans to that event.”

As they were chatting, I spied a super cool navy cashmere trench coat hanging on the antique armoire (very Dog Day Afternoon meetsBelle du Jour). I slipped it on and it fit like a glove.

“That looks dope,” Style Man said, “like it was made just for you.”

“What do you think, Jay?” I did a half spin in the mirror admiring the perfect fit. “Do you want to give it to me and I’ll be your brand ambassador?”

“Sorry. I can give you 25 percent off. On the brand ambassador meter you’re in the blue zone: Cool but not that cool or famous,” he shrugged.

“Although the column is helping,” he paused. “Which is why you now get 25 percent off instead of 10.”


L’actrice certainly knows how to command a room, especially her cavernous and sumptuous Upper East Side abode.

Her man, the Silver Fox, is Commander of our workout group, The Fifth Avenue Seals, so I had stopped by for a Saturday afternoon workout (cardio, stomach and weights) in their well-equipped gym, which was followed by the requisite glass of 1942 tequila for the Commander and a glass of rosé, for yours truly. (There are those who eat to live and those who work out to drink.)

“Do you know any rich or notable people who don’t pay for anything?” I asked L’actrice as we cooled off by the banquette in her endless kitchen.

“Is this for a new column?” She approved the artfully arranged charcuterie and crudité setup by her staff for her son and his friends, who were watching the football game, nary a lowly pretzel or chip in sight.

“It’s a companion piece from last month’s where people pay for fame,” I offered.

“Boy, do I have stories,” she said, shaking her layered, brunette Charlie’s Angels hair.

“Well, to start off with…” (She mentioned the portly scion of well-known fortune.) “…Whenever anyone goes out with him he never, ever pays for dinner.”

“From what I hear, he is not known as being particularly scintillating either. What’s the attraction?” I asked.

“He obviously thinks or has been told, that it is a privilege to be in his presence. And, let’s face it, some people like being around the name and are willing to pay for it.” She lifted her crystal goblet. I poured her a glass of rosé to further lubricate the conversation.

“Also, there was this very wealthy, foreign couple we were friendly with for years. We hosted them many times; both in the city and the Hamptons.”

“And?” I leaned in knowing something special was coming, as L’actrice is a font of great uptown information.

“Well, they were very proper … the Lady so- and-so … yet every time we went out to dinner, the husband would get up and excuse himself to take ‘a walk’ just as the bill was about to arrive. At first it seemed odd, then it became apparent that he would take a walk so he would never have to pay for dinner.”

“Oh, he had bill radar,” I sympathized. “The good old disappearing act!”

“Yes. And then one year they invited us to their grand estate in the country (she mentioned an aristocratic locale) and we went with a few friends expecting … a certain level of reciprocity.”


“And after the weekend we were all billed for food, drinks and transportation. Can you imagine?” She shook her head.

“Actually, no. Did you say anything to them?” I asked in disbelief.

“Of course,” she said, downing the pale liquid. “I told them the friendship is over. They, of course, had a hard time understanding what the issue was…”

It has been my experience that there are two types of people. Those who have to pay for everything and those who have everything paid for. I, for one, am in the former camp and always have the privilege of paying full freight for seemingly everyone and everything. When one runs an ad agency, it’s practically a reflex to pull out the wallet. I so often reach for the bill that it’s become automatic muscle memory.

Not so for the high-ranking Swiss playboy, who turned up at my friend’s South of the Highway manse last July 4, trailed by the staff lugging his Louis Vuitton luggage up the stairs.

Lanky, rich and social, he sported his blonde, tanned and leonine girlfriend like his vintage Patek Philippe. No need for a hotel reservation or a summer rental for these two—they nonchalantly made themselves entirely at home within minutes.

“Gruezi.” He smiled at me in his formal Swiss/German looking like an early Gunter Sachs photo in a Hamptons cocktail table book.

“A pleasure.” I extended my hand into his iron grip. “And he is?” I whispered.

“He’s an old friend and called to say he was in town,” my friend revealed.

‘There is an attitude among many of the more successful people that everyone owes them for something and that being in their incredibly successful presence is a treat.’

“And they just moved right in?” I raised an eyebrow.

“I enjoy the company, plus when I’m in Rome I might stay in his flat near the Borghese or on his sailboat in Bodrum. Not that it’s a boat,mind you.”

“So he never stays in a hotel?”

“Why should he when he has the run of my place? He’s only in from Geneva for two nights,” he shrugged.

The stunning girlfriend emerged from the pool in a postage stamp-sized Emilio Pucci string bikini and a cowboy hat, to the dismay of one or two of the married women in flowing St. Barth beach cover-ups.

“Dah-link,” she said to my friend in her clipped European accent. “Do you have any champagne or ggg-rosé?”

The host smiled brightly. “Take what you want. Mi casa su casa.” He called for his staff to direct her to the wine vault.

“What are we doing for dinner tonight?” Swiss Playboy asked my friend as he reclined on the chaise like a regal pasha.

“We’re all going to so-and-so’s dinner party,” my friend said. “I told her to add two more place settings.”

“Vonderbar! You’ll bring a good bottle from us? We didn’t have time to stop at the liquor store and I despise showing up empty handed.”

“Of course.”

“Perfect.” He reclined, calling after his girlfriend. “Darlink, can you bring me a glass of Domaine Ott. Oh and see if there are any olives, fromage or paté lying about.”

“Of course, luffy,” his girlfriend called, walking into the pantry and rummaging about.

As we chatted, I asked Swiss Playboy a few personal questions.

“So, do you consider yourself a playboy?” I asked.

“If I’m not,” he yawned, “who is? Did you say you were leafing for Spain and Italy?”

“Yes, on Sunday,” I replied.

“Where are you staying in Madrid and Barcelona?”

I mentioned two well-regarded hotels.

He raised an eyebrow, as if I had suddenly revealed my lack of pull. “You don’t have any friends who have houses there?” he asked.

“No. I am not plugged into those cities,” I confessed. “I haven’t been to Spain in years.”

“Too bad we didn’t meet earlier. I would have called my friend The Marquis of So-and-So for you. He would have let you stay in his palace. It’s heavenly.”

“Oh, I just love the Peacock Suite,” his girlfriend nodded in agreement.

“No, that’s so-and-so’s villa, Chou Chou.” He dismissed her mistake with a jaundiced eye, as if he were wearing a monocle.

“My mistake,” she said sweetly. “But it is wonderful.”

“I’m just a regular tourist staying at the (five-star hotel),” I said.

“Well,” he shrugged, nibbling on an olive flashing his gold signet pinkie ring, “one has to make do, doesn’t one?”

Illustration by Neil Webb
Illustration by Neil Webb

We made our way on a frigid night to the new and divine Polo Club restaurant. The lighting is warm and flattering, the food hearty and delicious. We were thrilled someone in town finally understood the importance of gracious, accommodating and good-looking staff, a piping popover and mouthwatering French fries. We were catching up with a new couple, our friends, Golf Buddy and the Queen of Kings Point.

“Everyone always thinks I’m Puerto Rican or Persian,” she said, referencing her lovely café au lait skin and smiling in delight at her new beau. Both are divorcées basking in romance’s new glow, his boyish, preppy looks a contrast to her leather, fur and jewels courtesy of her luxury jewelry business.

“Congrats, I saw the piece The New York Observer did on the ‘wealfies,’ ” she said. “What’s the next one?”

“I’m doing a piece on rich and notable people who don’t pay for anything.”

“You mean half of my clients,” she laughed. She mentioned three or four high-powered social and wealthy wives and heiresses who borrow but never buy.

“So and so just borrowed today,” she said, mentioning a very social heiress. “She just had an event tonight and borrowed three or four pieces. She is great and everyone loves her. Have you met?”

“No. What is it that she actually does?” I asked.

“She is very social and beloved. She is always at an event or on a private plane.”

“What does she do though? I asked.

“Her job…” Q of KP said in all seriousness, “is to get free things and to go out.”

“Does she ever pay for anything?”

“Not a thing.”


I was picking up the delectable salmon salad and lemons at Gentiles market on Madison when I ran into a charter member of the LSC (Lucky Sperm Club) who was sporting a deep tan, full Moncler regalia and was not at all shy about vaping in full view.

He rushed over. “Richard! Happy New Year!

“Happy New Year,” I smiled. “How was your vacation? You seem tan and relaxed.”

“I may be tan, but far from relaxed,” he grimaced. “I need a vacation from my vacation.”

“Why, what happened?” I squeezed one of the museum-quality lemons on display.

“Every year we have to go to [he mentioned a truly exclusive and ultra expensive five-star resort in the Caribbean] with my in-laws [a socially prominent family whose patriarch is known to control the purse strings]. It’s a command performance.”

“What’s so terrible about that?” I asked.

 ‘Every time we went out to dinner, the husband would get up and excuse himself to take “a walk” just as the bill was about to arrive. At first it seemed odd, then it became apparent that he would take a walk so he would never have to pay for dinner.’

“Well, we have to be completely on their schedule. Every meal is together. Everyone has to eat at 6 sharp. I have to be on call to play golf with him and I have to be on my best behavior.”

“Well, why don’t you take your wife and kids on your own vacation?” I asked.

“It doesn’t work that way. Harold [not his real name] pays for everything and wouldn’t like it,” he said.

“Well, what’s wrong with that?” I said.

“Richard, you don’t understand. It’s all about Harold. And no one wants to upset Harold.”

“Why not?”

“You know,” he looked at me, searching my eyes for recognition.

“Know what?” I asked.

“It’s all about the money. He controls everyone with the money. He stamped his $895 Margiela sneaker.

Look at it this way,” I smiled, “no one is taking me and my family away to an exclusive five-star resort in the Caribbean and footing the bill.”

“Yes, but you don’t have the pressure. You can go and do what you want when you want to do it,” he whined.

“Yes, but I have to pay for it.”

“So do I, my friend, so do I,” he took another puff on the vaporizer as he looked at his Franck Muller Master Banker and walked out the door into oncoming traffic.


The Mendel furs were out in full force as Dana and I met Park Avenue Prince and Princess at the Ludlow Hotel for cocktails and dinner at the Dirty French.

Joining us was one of New York’s newest real estate moguls and his wife, Nouvelle Social Powerhouse.

Known for her thoughtful generosity and creativity, Park Avenue Princess came armed with a bag of artfully wrapped gifts, including boxes of chocolate-covered pretzels for each couple and a palette of cutting-edge eye shadows for the women.

I knew this group would have an interesting take on what I have started calling “freeloading up” as there is always a fight for the check. These self-made men are the first to pull out their wallet and treat.

“I call it the slow draw,” the new real estate mogul observed. “There are the men that put their hand in their pocket very, very slowly and they never, ever get to the plastic,” he shrugged.

“And?” I leaned in, slicing the blood red beet and candied cashew.

“And then I take out my credit card and I pay for dinner.”

“But the best is the response,” Nouvelle Social Powerhouse said, leaning in. “They always say, ‘You really shouldn’t have,’ or have the look of surprise and faux anger after the bill is safely paid.”

“And then they go on and on about how generous we are and how we shouldn’t have,” he shrugged. “But I have yet to see an Amex or MasterCard appear on the table.”

Park Avenue Prince mentioned two or three press-worthy couples noted for their net worth. “I love those people,” she said. “They’re just too rich.”

“So, you’re saying they’re too rich for money?” I asked.

“You could say that. By not having any money on them it says they have the most money. Or they make a donation to your charity or help you with a private school and then feel they should have a year of free dinners.”

As the waiter brought out the desserts, Dana shot me a glance to do what is called the “preemptive strike,” going to the bathroom but slipping the maître d’ my credit card. To my dismay, Real Estate Mogul had already beat me to it and the waiter brought over the two credit cards in silver cups so we could split the bill.

“Wait, that isn’t fair,” Park Avenue Prince reacted strongly, trying to get his black card in the mix.

“No worries,” I said. “I think you paid last time.”

“Thank you,” he said, looking like a lost puppy. “I’m just not used to being paid for.”

“I know,” I said. “It’s a strange feeling.”

“You were very quick on the draw, Richard,” Real Estate Mogul shook his head in approval.

“Yes, but it just proves I’m just not rich enough not to carry around money.”

“I love you anyway,” Dana said adoringly.


It was a wintry night in East Hampton and the Palm was packed to the rafters. We were meeting Best Man and Second Wife for Dana’s celebratory birthday dinner.

“There’s nothing ruder than table lingering,I said as a number of couples came over to say hello and one lingered well into our appetizer course.

At that moment, a man walked over to the next table and had a half-hour conversation with his derriere invading our personal space. “This is so rude,” Second Wife said, his backside two inches from her solid-gold Daytona.

“Nothing is worse than ass lingering.” I shook my head, hoping he would find somewhere else to plant his unsightly and wide backside. To top it off he was wearing chinos.

Dana reached out and flicked his behind, but it was too padded for him to feel anything.

“Do you have any stories on rich people who don’t pay for anything?” I implored Second Wife.

“My line for that is ‘short arms, long pockets.’ They can never find their wallet as they’re reaching for it,” she said, looking shimmery in the Ramy Brook top named for her.

“I know that type quite well,” I said.

“There are a number of people that never pay,” she remarked as she ate her crabmeat salad. “There is an attitude among many of the more successful people that everyone owes them for something and that being in their incredibly successful presence is a treat,” she shrugged.

“And then they’ll order the $900 bottle of wine to boot. It’s like tonight Richard, I’m ordering the lobster because I know you’re paying,” she laughed in all seriousness.

“Have whatever you like. That’s because you are my second wife. Order away. In fact, I just ran into (Lucky Sperm Club) yesterday and he was moaning and groaning about having to go on vacation with his father–in-law.”

‘I think it’s also a function of age and where you are in your life,’ Dana explained. ‘When we were in our 20s everyone chipped in. Now you have to ante up.’

“Oh, I love those people whose in-laws or parents who pay for every vacation, private school and summer camp tuition and then all they do is complain about them.” She rolled her eyes.

“They’re only one step evolved from the professional moochers,” I laughed. “You know the type, people always catching rides on someone’s private plane or bumming a room at their hotel villa, and thinking they’re doing you the favor.”

“As if anyone wants to see them in a bikini and have to pay for it,” Second Wife said.

“It’s like paying to watch a bad movie,” I shrugged at the thought of unappreciative houseguests who look better in clothes. “I may need to designate a ‘cellulite free zone’ when I extend an invitation. If someone is going to mooch off my villa, shouldn’t they be Victoria’s Secret runway ready?”

“Look,” she stated, “Best Man (her husband) has more guests than the Four Seasons and no one brings a bottle or lifts a finger. I can assure you.”

I stirred the pot. “Didn’t you have someone’s son living with you for six months?” I asked.

“Oh that one,” she replied. “He was very nice. The children liked him.”

“Did the parents send anything or offer to pay?” I asked.

“Nada, y’all”

“Amazing,” I groused. “And then all the progeny who fly to private islands paid for by the parents. I don’t see anyone giving me a free vacation to a luxury five-star resort.”

“That’s because you and (she mentioned her husband Best Man) pay for everyone and everything. You’re both soft touches.”

As if on cue, our other guests all arrived and within minutes ordered super-sized lobsters. (For the record: In our group of friends, when it’s a spouse’s birthday the husband or wife usually picks up the bill.)

“Richard, you are sooo generous,” one of our friends said, toying with her eight-pound lobster claw.

“I may be,” I joked. “But imagine what everyone would say when they left the birthday dinner if I didn’t pick up the tab. You’d all say, ‘Can you believe he didn’t pay?’ ”

“You’re so right,” one of the other guests added. “But I feel close enough to tell you that.”

“I think it’s also a function of age and where you are in your life,” Dana explained. “When we were in our 20s everyone chipped in. Now you have to ante up,” she declared as everyone nodded in agreement.

After I paid the significant bill, Second Wife and I walked to the crowded entrance as we retrieved our coats.

“I love your coat. Is that a cashmere trench?” she asked, fingering the material.

“Yes, Jay Kos. Twenty-five percent off.”

“It fits like a glove,” she said, scooping up a few packaged after-dinner mints, handing  them to me.

“Don’t say you never get anything for free,” she winked.

“Thanks,” I said, relishing the gesture.

“Between the mints and the discount,” I smiled, “clearly, I’m starting to move up in the world.”

“Wait. Do you have a five or a 10 for the car valet?” Second Wife asked me.

“Of course,” I said, digging into my pocket for cash.

“That’s my man! Long arms, short pockets, baaaaby.” 

Too Rich for Money: Power-Mooching Among the Beau Monde