Looking Back At Trump’s Years-Long Obsession With Oversized Airplanes

As diplomats around the world struggle to figure out Trump, Qatar may have found the perfect way to please the American president—dangling a supersized gift to stroke his ego.

Donald Trump has plane envy. “You look at some of the Arab countries, and the planes they have parked alongside the United States of America’s plane—it’s like from a different planet,” he marveled Monday. To compensate, Trump is now considering accepting a plane from Qatar, an energy-rich monarchy that has long sought to curry favor with the U.S. president. “A very nice gesture,” Trump said.

Also a gesture that plays directly to the ego of a billionaire who has long preferred oversized planes, personalizing airliners too big to land in some airports over the more nimble jets that most executives prefer. Trump’s planes, impractical as they may be, definitely make a statement. “From an ego standpoint, hey, you land with an aircraft like that,” says aviation pro George Reenstra, “you can interpret that the way you want.” Alan Marcus, a communications consultant who used to ride on Trump’s old Boeing 727, interprets it like this: “It’s an extension of who’s got the biggest penis.”

In the late 1980s, when Donald Trump was making all sorts of ego-fueled purchases, like the Plaza Hotel and a professional football team, he bought part of struggling Eastern Airlines, then converted it into Trump Shuttle, a service connecting New York, Boston and Washington, D.C. The business flopped, but Trump snapped up one of its Boeing 727s and converted it into his personal jet. Trump’s plane fit the era–velvety red chairs, rich wooden tables, thickly framed art. “It always looked good,” says Marcus. “But, for example, it didn’t have noise arresters on it, so we couldn’t land at LaGuardia after, I think it was 11 o’clock at night. And I remember the first time I was on the plane, I said, ‘What else is missing?’”

Trump, whose representatives did not respond to a request for comment, decided to upgrade eventually. In 2008, he approached broker Ben Sirimanne, interested in a Boeing 767. Sirimanne pointed out that it would be hard to land in some places. “So then he said, “All right, find me a 757,’” says Sirimanne, referring to a slightly smaller model that was still too big to land everywhere. The broker connected Trump with a friend, who lined up the plane of Microsoft cofounder Paul Allen, a 1991 Boeing 757.

Before purchasing the plane, Trump contacted another aircraft professional, Eric Roth, who specializes in tricking out interiors of private planes, sending him to take a look and bring back photos. Trump went ahead with the deal and got to work on the redesign, ultimately spending roughly $37 million on the plane. “As a developer, you’re going to have plenty of architects and designers on staff or certainly at your disposal,” says Roth. “And in this case, it wasn’t that at all. It was just him and myself.”

Drawing inspiration from Trump’s penthouse, Roth came up a design featuring marble, creams and an abundance of gold. Even the seat buckles received a 24-carat coating. Trump wanted a big TV, with a great sound system, to watch movies. He liked the idea of his family crest stitched into the headrests. And he had an unusual dining request. “An area in the galley for Oreos,” Roth laughs. “I said to him, ‘Mr. Trump, really?’ He goes, ‘I love Oreos.’”

Trump still owns the plane. He used Air Force One during his first term, then upgraded the 757 while out of office, adding, among other flourishes, a prominent American flag to its tail. Trump Force One, as the president’s fans sometimes refer to it, became a moneymaker during the 2024 presidential race, with Trump’s campaign funneling more than $5 million of donor money into his business as he jetted around the country.

Meanwhile, in Qatar, the country’s leaders have been seeking to offload two of their three Boeing 747s, each of which they purchased for $200 million and gave a VIP makeover for over $200 million more, according to Sirimanne, whom the petromonarchy contracted to help sell the jets. All that money left the planes in great shape, with just the sort of interiors that might pique the interest of Donald Trump—lots of creams, some wood, maybe not quite enough gold. In 2018, Qatar gave one of the planes—which sport two full bedrooms with en-suite bathrooms, three galleys, an office and multiple lounges—to Recep Tayyip Erdogan, the Turkish president. “The second airplane was just stagnating, just waiting to be sold,” says Sirimanne. The Qataris wanted $275 million for it, he says. “I brought them two offers around $200 million each, and they turned down both.”

Then, they came up with a different, perhaps more valuable, plan. “They just decided,” says Sirimanne, “it’s better to gift it to Trump than to just do maintenance on it.”

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