The Most Insane and Out-of-Touch Behaviors Staff Saw While Working for Billionaires
Billionaires move through life with a level of ease most people never experience. The people who work for them see what that ease looks like behind closed doors. Chefs, drivers, and house staff notice moments that feel unreal because they happen without a second thought. Everyday interactions like these show how disconnected some ultra-wealthy employers can be.
A Human Ham Slicer Shipped from Spain
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A Hamptons homeowner decided their Iberico ham needed a professional touch. They flew in a trained jamón slicer from Spain and hired him full-time to carve cured meat at beach house gatherings. The job was permanent. Guests were not expected to slice it themselves. The ham was considered too good for that.
The Dishwasher That Ran for Sport
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At one family’s mansion, no one bothered to unload the dishwasher. If a clean cycle had just finished and someone used a plate or cup, it went straight back in, and the machine was started again. This happened every day. Weeks passed without the dishwasher ever being emptied. One houseguest tried to unload it, only to be scolded for interfering with “the system.”
The $400,000 Tree for a Wedding Photo
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A billionaire once paid $350,000 to truck in a fully grown willow tree for his niece’s lakeside wedding photos. It was removed days later because he didn’t like how it looked. Landscaping crews spent another $50,000 restoring the area. The wedding lasted one afternoon. The tree lived there for less than a week.
A CEO Who Forgot the East Wing Collapsed
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When part of a CEO’s home collapsed due to weather damage, he didn’t find out until an HVAC tech stumbled into the mess during a routine maintenance call. That wing of the house hadn’t been visited in months. No one in the family had noticed. It was just one of many unused sections.
Evian Ice Cubes for 200-Year-Old Scotch
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Working on a private island, one staffer received a special request: use only Evian water to make ice. The guest believed tap water would ruin the flavor of his centuries-old scotch. The housekeeper had to freeze bottles of Evian in custom trays to make slow-melting cubes that wouldn’t taint the drink.
The Mansion Next Door, Bought Just for a Tent
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A wealthy family in the Hamptons needed more space for a party than their estate allowed. Rather than scale back, they bought the house next door, demolished it, and set up a large tent on the lot. The event lasted one evening. Afterward, the land was left empty.
A Pet Cat’s European Holiday
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A woman sent her butler and a private jet to escort her rare breed cat to a lakeside mansion in Italy because she felt the animal seemed “off.” She believed the cat needed a sunny vacation to lift its mood. The staff complied, and the cat reportedly lounged by the window for days.
$9,000 Stove, Never Used, Still in Storage
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Builders finished installing a luxury kitchen appliance—a $9,000 imported stove—before the homeowner decided she didn’t like the color. Rather than return it or donate it, she had it stored. Two years later, it still sat in a climate-controlled unit, untouched and fully functional.
A Dog Butler Reporting to the Human Butler
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In San Francisco, a mobile dog groomer was met not by the pet owner or even the main house staff, but by a dedicated dog butler. His job wasn’t to feed or walk the dogs; it was just to schedule their grooming and walking appointments. He reported directly to the household’s head butler.
Thanksgiving Parade Viewing with Six Private Jets
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To watch the Macy’s Thanksgiving Day Parade from a New York hotel suite, one matriarch flew in her entire extended family—each on their own private jet. Staff traveled separately and were forbidden from staying on the same floor. The top floor of the Ritz-Carlton was booked entirely for the family’s parade viewing party.