How the private jet became the singular fetish and status marker of the modern superrich

In the summer of 1999, soon after Teddy Forstmann, the late billionaire pioneer of leveraged buyouts, completed the sale of Gulfstream, the private-jet manufacturer, to General Dynamics, Gulfstream’s board of directors asked him what he wanted as a gift for successfully engineering the company’s turnaround and sale. It turned out to be the very moment private jets went from being merely an exclusive form of fast transportation to a form of rarefied and much-coveted currency.

Forstmann Little, Forstmann’s private-equity firm, had bought Gulfstream for about $850 million from the Chrysler Corporation in 1990. When he opened the box, Forstmann found a bloated, poorly run business. He was pissed. But rather than sit back and watch the company descend into seemingly inevitable bankruptcy, Forstmann eventually took over as CEO, reversed Gulfstream’s fortunes, engineered an initial public offering in 1996, and then sold the company for $5.3 billion. In nine years, he had delivered to investors a $5 billion profit on an original equity investment of about $200 million. The deal became legendary on Wall Street. “I’m an artist and Gulfstream was a big canvas,” Forstmann once told me in an interview about a decade ago.

Robert Strauss, the ultimate Washington insider and Akin Gump partner, was chairman of the Gulfstream board, which Forstmann had stacked with his friends, a variety of luminaries and powerful former government officials such as Henry Kissinger, Colin Powell, Donald Rumsfeld, George Shultz, Roger Penske, Michael Ovitz, and Lynn Forester. “What do you want?” Strauss asked Forstmann. “We’ve got to give you something? What about some options?” “I own so much stock,” the canny Forstmann replied. “I don’t want to have options.” Forstmann thought about Strauss’s request and called him back. “I know what I want,” Forstmann told him. “I want a G Five,” referring to the company’s then-state-of -the-art private jet. “Holy shit,” Strauss replied, stunned at the audacity of Forstmann’s request. “Think about it,” Forstmann said to him. “It’s forty million bucks. You were going to give me more than $40 million worth of stock anyway.” Strauss conceded that point to Forstmann and then discussed the novel request with the Gulfstream board . Needless to say, Forstmann got his own personal Gulfstream V.

One of the revelations of the Jeffrey Epstein scandal was the degree to which the private jet has become the definitive, highly overdetermined artifact of modern super money culture. Epstein’s plane (even if it was an older secondhand model) certified his wealth, earned him chits with academics and former presidents, served as a stage where he could perform his grift, and of course helped him groom his prey in his sick sex scheme.

Private air travel dazzles everyone, and once you fly this way, you’re hooked. Former presidents like to ride on private jets: Bill Clinton, of course, who’s famously, problematically addicted to private jets, but also Barack Obama. Donald Trump has placed a model of one of the two yet-to-be-configured Air Force Ones smack-dab in the middle of the Oval Office.

Harvard scientists, Nobel Prize winners, narcissistic defense attorneys love to fly private too. Setting foot on the tarmac confers an irresistible, intoxicating feeling of specialness. Avoiding security is the very definition of modern luxury, marking a bright line between private-jet owners and their lucky guests, and the merely rich . Even first-class commercial fliers, with their little glasses of Champagne, their special blankets, are schmucks, fenced off in pens, forced to take off their shoes like everyone else.

Private jets have become the essential element of modern superrich business and pleasure infrastructure, woven in deeply, the communal living space for the most acquisitive, rapacious people in the world. Can you imagine how inconvenient it would be for the global elite to talk about climate change at the World Economic Forum in Davos, or at the Allen & Company Sun Valley Conference, or at the Aspen Institute in Colorado, or at the Bilderberg Meetings–this year in Montreux, Switzerland-without traveling there on their private jets?

A personal, commercial-size private jet was not yet the coin of the rich-guy realm when Forstmann made his bold request–Hugh Hefner made a big show of having a plane, an airborne Playboy Mansion, and of course there was Air Force One, since 1962, the definitive superpower ride. Jackie Kennedy’s robin’s-egg -blue paint job was the ur-customization, beginning to show what was possible when you had power over your own plane. But during the ’90s, the trend definitely began to build. Business titans got addicted. Jack Welch, the legendary CEO of GE who turned the company into the most valuable and most admired in the world, also put a premium on having unlimited, free access to a private jet after he retired in 2001–he had gotten used to traveling privately as a GE executive. Thanks to an “employment and post-retirement consulting agreement” with GE that Welch signed in December 1996, he would have “access to GE aircraft for unlimited personal use and business travel,” among other perquisites. The precise details of Welch’s delicious post-retirement contract were not fully known from GE’s public filings.

But in 2002, in the middle of his acrimonious divorce from Jane Beasley Welch, his second wife of13 years, she revealed the details in a court filing. Jane Welch’s expert valued her ex-husband’s annual use of a GE-owned Boeing 737 at about $3.5 million, or nearly $300,000 per month .

The essential purpose of a Gulfstream V of one’s own or unlimited access to a Boeing Business Jet was to keep a safe distance from the masses-what the writer Tom Wolfe described in The Bonfire of the Vanities as a need to “Insulate, insulate, insulate.” It may be even truer today, except that the Gulfstream V has become the G650ER-the speed record holder for the farthest flight in private-jet history, going from Singapore to Tucson, a distance of 8,379 nautical miles. And there are other options for the top 1 percent of the 1 percent than there were in 1999, when Gulfstream sold 141 planes before the company had any serious competition. Now Bombardier makes the much coveted Global Express jet; Textron’s Cessna division makes the Citation Longitude, an upgrade from its beloved Citation X; Boeing still makes a business jet, as do Dassault and Embraer. For the aspirational class-mere eight-figure millionaires-there’s been the rise-and acceptance-of fractional jet operators, such as Net Jets, which Forstmann had a hand in starting and is now owned by Warren Buffett, and the upstart, Wheels Up, which just raised $128 million at a valuation of more than $1 billion.

A jet often announces a superrich arrival. One of the first things the Google founders Sergey Brin and Larry Page did after becoming billionaires-thanks to the IPO of Google in 2004-was to buy a used Boeing 767-200 from Qantas, the Australian airline, for $15 million-a relative bargain-and then spend another $10 million refurbishing it with two staterooms, a shower, a dining area, a lounge, and 15 first-class seats and the ability to seat 50 passengers. That was only the beginning. Reportedly since then, Blue City Holdings, the company they created to own their jet fleet, has bought another eight jets, including two Gulfstream Vs and another Boeing, and built a private hangar, at a cost of around $82 million, in San Jose, California.

It’s not at all a surprise, given that their owners have reached the World Series of acquisitiveness, that jets are highly competitive, subject to constant comparisons of size and number. A few years back, I wrote a profile in this magazine about Prince Alwaleed bin Talal, the Saudi prince and businessman who was then worth around $27 billion. He was one of the largest, shareholders in Citigroup, News Corporation, Apple, and Twitter. He had a lot of toys, among them a Boeing 747 outfitted with a gold throne, and a Hawker Siddley 125. He told me he was the only private citizen with a Boeing 747 and the rumors that Brin and Page had one were not true. He said he knew they had a Boeing 787. (In fact it was the customized 767-200.) He had also just bought an Airbus A380, the only private citizen to order one of those.

Mark Cuban, the billionaire tech entrepreneur, Shark Tank regular, and owner of the Dallas Mavericks, bought his first private jet-a Gulfstream V-on the internet for $40 million. After his pilot gave the plane a test drive and approved of it, Cuban wired the money. “I bought it to save time,” he emailed me. “I’m a believer that time is the most valuable asset we can’t own. Anything I can do to spend more time with family is a win.” He has since bought two Boeing jets, one of which he had specially redesigned to accommodate the Mavericks.

A private plane is alchemical, translating a nine-figure bank account into actual power (harder than it sometimes looks, for some people). “For people who are actually not that powerful except that they have a lot of money, it gives them a calling card to have power,” one private-equity mogul explains to me. “It’s all about currency. They get to leave when they want . They get to arrive when they want, and they get to make their friends be on their schedule . And then if they are really dicks, they can leave them when they are late.” Forstmann once did that to a guy who was 20 minutes late for a flight, after he got stuck in heavy Manhattan traffic during the annual United Nations General Assembly meeting. When another passenger on the plane asked Forstmann to wait, he was told, “Fuck him. I’ve got things to do.”

A private jet forms covalent bonds of the kind that pay off later-to the acquisitive class, just about the only kind that matter. A ride in a private jet creates people that owe you something, debts if only of gratitude. “There’s this whole New York to Florida trade on the weekends in the winter where it’s like, ‘Hey, you want to ride?'” continues the executive. “Because it’s not like they fly capacity. You use your Net Jet and you take one person, you can curry seven favors. You are like king for the day.” Who knows the amount of goodwill that Steve Rattner, the former investment banker and Obama car czar, generated by giving MSNBC host Joe Scarborough an occasional lift back and forth to Martha’s Vineyard on the Dassault Falcon 2000 jet that Rattner pilots himself? Rattner, and his charts, has been a Morning Joe regular feature for years.

One’s jet is one’s castle, where the billionaire makes the rules. These can get pervy. According to an age discrimination lawsuit filed (and later settled) by a male pilot against Mike Jeffries, then the CEO of Abercrombie & Fitch, there were strict rules, contained in a 47-page manual, for how the young, male, scantily clad models were supposed to behave while crewing on the company’s Gulfstream G550. Male flight crew were told to present themselves clean-shaven in a uniform of Abercrombie polo shirts, boxer briefs, flip-flops, and gloves (black for when handling silverware and white for laying the table) … and wearing a “spritz” of the retailer’s own brand of aftershave.

There is also an infamous story about the time a group of clothing executives was flying back from a fashion show in Europe. A female model was also on board. It was Halloween time . The plane was festooned with little gourds and miniature pumpkins. “These guys were all fucking hammered,” says someone familiar with the incident, “and were throwing the pumpkins at each other on the plane. And I guess they threw one and hit the model in the face and cut her eye. They trashed the airplane.” He says the model sued for the damage done to her face. The jet owner sent the executives a bill for $80,000.

Epstein’s plane, like his town house, was oversexed kitsch. “It was really cheesy with the zebra skins and the leopard pillows,” says Jim Dowd, one of Epstein’s substitute former pilots. “He had, like, this big round bed with mirrors on the walls.” One pilot told ~e the story of how he was flying a private jet when Epstein and Ghislaine Maxwell hit the jackpot for bad behavior. Epstein had been invited to travel on a friend’s jet from Palm Beach back to New York City. First, he arrives 20 minutes late. (Strike one.) Then, he showed up with Maxwell, who hadn’t been invited. (Strike two.) The jet had a bed room for the billionaire to sleep on overnight trips to Europe. About halfway into the two-hour flight, the pilot went back to check on his boss, to see if he needed anything. He didn’t see Epstein or Maxwell. But he saw that the jet’s owner was plenty pissed. “They’re in the back fucking with the doors closed,” the pilot says. “Epstein and Ghislaine. And you can hear them. I mean, really? It’s a two-hour flight.” (Strike three.)

Forstmann liked to send his empty Gulfstream jet over to Luton Airport, in London, to pick up Princess Diana, then separated from Prince Charles, and bring her back to Westhampton, on Long Island, to be with him. On the way to London, Forstmann’s otherwise empty jet would have on it the two pilots flying, plus another two pilots for the way back (with the first set of pilots flying back commercial), and one or two flight attendants. How the princess was listed on the flight manifest was a matter of some debate since there are criminal penalties for lying on FAA records. “There was a huge fight about what was actually sighed for,” says someone familiar with what transpired. “And ultimately, we got to Diane Spencer, handwritten. It could be some cleaning lady.”

The pilots and crew on these planes get to travel widely and see how the other halflives, of course. But it’s not a picnic. You are always on calL You’d better get along with the other pilots and the flight attendants, because they are almost always the same people. You’re never quite sure where you are going and when and for how long. “You’re going to fly 30, 40 hours a month,” Dowd tells me, “but you do a lot of sitting. You fly to Aspen and sit there for two, three, four days. You fly to Palm Beach and sit there for two, three, four days… You could be in some great places, but you’re not with who you want to be with.”

Jets are deeply tied to their owners’ status, their ego, their very being . The writer Rich Cohen once traveled on Jann Wenner’s Gulfstream II jet to follow the Rolling Stones tour. He recalled leaving Teterboro, New Jersey, with another Rolling Stone editor to fly to East Hampton to pick up Wenner, then the owner of the magazine, for the flight to Toronto to see the band perform that night. “We were sitting on the runway,” Cohen recalls, “and, like, a G Four taxied next to us and Jann went crazy about how, ‘Now, my plane looks like a piece of shit.’ He was being half sarcastic, but there was just an element of seriousness about it that was very funny.” Other business executives complain about how pathetic they feel when they lose a job where they had regular access to a private jet and then don’t. “The plane is the game changer,” Cohen says. “Basically, there are people with the plane and people without the plane, and those are the only two classes that matter. Once you have a plane, that’s it. And if you have a plane, to go to a job where you don’t have a plane, you almost can’t do it.” A couple of years before Wenner sold his company, he had to sell his jet.

Forstmann was one of the first to realize that a whole new class of uber-wealthy Wall Street deal guys, like him, had emerged and would not be able to resist owning a private jet, not only for its efficiency and the freedom it provided but also as the ultimate status symbol that virtually screams: Fuck you. Ironically, he was also scared to death of flying. His regular seat on the jet had indentation marks from where he gripped it so tightly in fear. “The reason that he was so interested in Gulfstream was because it was the only way he could do his business,” says someone who knew him well. “Because otherwise, he couldn’t. It sounds crazy but he couldn’t get on a commercial flight.”

When Forstmann first bought Gulfstream, he remembered asking the head of sales at the company how he went about making a pitch. “When you are selling a plane, how do you do it?” Forstmann asked him. “What do you mean?” the guy responded. “He’s the head of sales,” Forstmann reminded me . “I said, I mean, how do you do it? Who do you call?” He said, “I don’t understand the question.” “You’re trying to make a sale,” Forstmann persisted. “You’re going to call somebody. Whom do you call? Do you call the CEO, the CFO? Who do you call?” “Oh, I get what you’re saying,” he replied, finally . “We’re Gulfstream. We don’t make calls. We take orders.” “He was a great guy, a really nice guy, but he was gone in a week,” Forstmann told me.

And for those people who can’t afford their own private jet, a Moscow-based company, Private Jet Studio, lets them pretend that they can by allowing anyone to pose next to and inside a Gulfstream jet while it remains firmly on the ground the entire time. For around $200 for a two-hour session, a photographer will take pictures of you and your fabulous pretend private jet, all of which, of course, can be immediately posted on Instagram for wider circulation and general fabulousness . The private-jet tarmac can also be a place for private meetings…