Trump is a president with a deep history with aviation. Now, he’s designed his own Air Force One
By Alexandra Skores, CNN
Washington, DC (CNN) — There had never been a US president who’d spent most of his pre-White House career jetting around the world in planes with his name on the side or even running his own airline.
Until President Donald Trump.
“I love aviation,” Trump told troops last year on the USS George Washington in Japan.
Now, Trump is making his mark on presidential aircraft, with three Boeing 747-800s – including a jet donated by the government of Qatar and unveiled Friday – being modified to his specifications.
“To accelerate delivery, the modification program prioritized critical mission requirements over aesthetics,” a senior administration official told CNN regarding the donated jet, adding there were “no shortcuts taken.”
The Air Force One fleet adjustments mark the latest chapter in Trump’s interest in air travel, from running an entire airline of designer Boeing 727s shuttling business travelers between New York, Washington, and Boston, to picking out gold-plated seat belts for his personal jets. Yet, he’s said he doesn’t like to travel.
Both personally and professionally, Trump has made aviation a centerpiece of his brand of wealth and power.
A brother with dreams of flying
All Fred Trump Jr. ever wanted to be was a pilot.
The president’s brother, nearly eight years his senior, didn’t want to go into the family real estate business, but dreamed of flying for Trans World Airlines. TWA was one of the earliest US airlines, but was eventually acquired by American Airlines.
“What he loved doing was flying airplanes,” Donald Trump told the Washington Post in 2019. “I remember being at the house and other pilots from TWA would come to the house and they’d come to work with Fred because he was a very natural talent.”
Fred Trump Jr. flew for a few months in 1964 as a secondary pilot and was in the airline’s flight school but faced mounting pressure from his family to join the Trump businesses, The Washington Post reported.
“Come on, Freddy, what are you doing?” Trump told his brother, according to the Washington Post. “You’re wasting your time.”
Their father, Fred Trump Sr., called being a pilot nothing more than “a chauffeur in the sky,” his son’s friend told the paper.
Fred Trump Jr. died of a heart attack in 1981, which the family blamed on alcohol, at just 42 years old. At the same time, his younger brother Donald’s career was on the ascent as he built his most famous building, Trump Tower.
“Watching what happened to Fred, I learned to study people closely and always to keep my guard up, in both my personal and my professional life,” Trump wrote in his book, “Surviving at the Top,” coauthored with Charles Leerhsen. “Fred was truly one of my great teachers.”
A Trump airline
Cheers erupted in the Trump Organization’s suite of offices in Trump Tower at 5 p.m. on May 24, 1989, Trump wrote in “Surviving at the Top.”
A court had just cleared the way for him to buy an airline.
Trump purchased Eastern Air Lines’ most profitable asset, the Eastern Shuttle, which flew between New York, Washington and Boston, for $365 million. The deal – which some experts considered overpriced – included landing rights, a small fleet of older Boeing 727 planes and terminals, all of which Trump promised to make luxurious.
The idea started when Trump was approached at a cocktail party in the spring of 1988 by Frank Lorenzo, the corporate raider who controlled Eastern Air Lines.
“(I) just said, if our board ever decided to sell, would you have any interest in looking at Eastern Air Lines’ shuttle?” Lorenzo told CNN in an interview. “He said maybe, that’s interesting and then he called me the following week.”
The airline industry was very different at the time – a decade after deregulation and years before Amtrak’s high speed Acela trains would appear – PanAm Airways and Eastern Air Lines dominated travel in the Northeast corridor.
After Eastern Air Lines declared bankruptcy in March 1989 and a competing bid from America West Airlines failed, Trump would renegotiate his purchase to include an additional five Boeing 727s from Eastern’s fleet, he wrote in “Surviving at the Top.”
“He’s a good negotiator and he knew what he wanted,” Lorenzo said.
Eastern’s former planes were painted with one word: “TRUMP.”
“What I want to do is run it like a diamond. An absolute diamond,” Trump said when the deal was announced.
Henry Harteveldt was the first marketing director for the Trump Shuttle and worked closely with Trump to launch the airline.
“Mr. Trump saw it as a both a marketing as well as business opportunity,” Harteveldt told CNN. “Obviously, having a fleet of more than 20 Boeing 727s, flying between three of the most important cities in the country is a great advertisement for your brand, which at the time was heavily focused on his residential real estate development and his branded casinos.”
“Mr. Trump was understandably very, very involved in things like marketing, brand, the passenger experience and other areas, because, as he kept telling us, it’s his name on the side of the plane,” Harteveldt said. “He wanted people to have a very good experience.”
The first test for the Trump Shuttle
The Trump Shuttle operated flights every hour on the hour. Like Eastern, the airline promised passengers that if a flight was full, the shuttle would roll out a second plane – even for just one passenger.
“Truthfully, it was great for the Trump ego,” Trump said after seeing some of his other properties on the first flight to Washington in 1989. “I’m not supposed to say that, I guess, but it was great for the Trump ego.”
Foreshadowing Trump’s 2016 presidential run, still more than a quarter century in the future, a reporter at the ribbon cutting for the new airline in Washington, DC, compared it to a campaign stop.
“You believe this?” Trump responded, laughing. “That’s right, there are no vacancies. No. I love what I’m doing. I enjoy what I’m doing. I think I do it well. I want to run this and I want to run everything else I have perfectly.”
The ambitious airline faced its first crisis just a few months after the first flight.
On August 10, 1989, Trump was in his office on the phone when an employee interrupted him, he wrote in his book.
One of his planes was in trouble.
The nose landing gear on a 727 flying from New York’s LaGuardia to Boston Logan International Airport wouldn’t come down. The pilot, Captain Bob Smith, tried everything, but had no choice but to land without the front wheels.
Trump’s first instinct was to turn on the TV, he wrote in his book.
He saw CNN showing video of the plane skidding down the runway, sparks flying before eventually coming to a stop. The passengers evacuated on the runway.
Fifty-four people were on board and only two sustained minor injuries, the National Transportation Safety Board reported.
“I couldn’t believe things had gone as smoothly as it looked,” Trump would later write.
He got on one of the next Trump Shuttle flights to Boston where he would congratulate the pilots and focus on the positive.
The NTSB found a broken part prevented the wheels from dropping due to an incorrect assembly and the failure of Eastern Air Lines to administer a required inspection, all before Trump bought the plane.
“This was a great, great day as far as I’m concerned and as far as everybody else is concerned,” Trump said after he landed in Boston. “And I just came to shake Bob’s hand and everyone else’s hand, and I want to just congratulate them. What a great job.”
But exactly two months after the miracle landing in Boston, Trump would experience a major tragedy within the empire he was building.
‘A day that changed my life’
On October 10, 1989, the Trump Organization, which used a fleet of helicopters for travel to its casinos in Atlantic City, experienced its first deadly crash.
“I know the date because it was a day that changed my life,” Trump wrote in “Surviving at the Top.”
An Augusta 109 helicopter took off from Manhattan for a routine business flight to Atlantic City with three Trump executives onboard: Stephen Hyde, Mark Grossinger Etess and Jonathan Benanav. Trump was impressed by the men – all of whom held prominent roles in his businesses, he would reflect in his book.
“For an instant,” he considered going with them, he wrote, but there was too much to be done in his office in New York.
As the aircraft approached Atlantic City, a portion of one of the main rotor blades separated, the NTSB report showed, tearing the transmission and rotor apart and sending the helicopter crashing onto the Garden State Parkway.
The failure was due to a “manufacturing induced scratch” on the blade, caused by a sharp tool and inadequate quality control when it was built, the NTSB found.
It wasn’t until a reporter from CBS TV called Trump to ask for comment that he found out the executives and two pilots in the chopper had died, Trump recalled in “Surviving at the Top.” He dedicated the book to the three executives.
Trump said after the incident he “felt sadder than (he) ever felt in (his) life.”
“No one on earth can be totally secure, because nothing can completely protect you from life’s tragedies and the relentless passage of time,” he wrote.
Yet, more problems remained for Trump’s aviation ventures.
Just a few months after the Trump Shuttle’s first flights, the US entered an economic recession, which curtailed some business travel – the primary customers for the shuttle. About a year after the first flights, Iraq invaded Kuwait, sending jet fuel prices soaring. The situation mirrored some of the challenges US airlines faced this year with the spike in jet fuel prices caused by the war with Iran.
The luxury touches for the 45-minute flights, which Trump heralded at the airline’s launch, didn’t turn out to be enough. The compounding effects of high fuel costs along with the debt that helped finance the purchase and the upgrades to the planes accumulated quickly.
About a year after taking off, the airline defaulted on the first of its loans and by 1992, the Trump Shuttle was turned over to creditors who sold it to USAir, the New York Times reported.
The deal ended with Trump no longer responsible for some of the $245 million in loans left, and $100 million of the $135 million Trump personally guaranteed was forgiven, according to the Times.
Flying Trump style
For all his interest in aviation, Trump has previously said he doesn’t like to travel.
“Stay close to home” was one of his rules for success, according to “Surviving at the Top.”
“Travel is time consuming and, in my opinion, boring – especially compared to the fun I have doing deals in my office,” Trump wrote. “I can never understand people who say that if they had a lot of money, they would spend their time traveling. It’s just not my thing.”
But despite his aversion to traveling, Trump spent much of his career jetting around the world in his personal planes, resembling palaces with wings.
His first plane was a “lavishly equipped” Boeing 727, the same kind of plane the Trump Shuttle would later fly. He bought it from a “troubled” gas company in 1987, according to his book, “The Art of the Deal.”
“This plane could seat up to two hundred passengers, but it had been reconfigured for 15, and it included such luxuries as a bedroom, a full bath, and a separate working area,” he wrote. “It was a little more plane than I needed, but I find it hard to resist a good deal when the opportunity presents itself.”
A new Boeing 727 was worth about $30 million at the time, Trump said.
Trump wrote he made a “ridiculously low” offer of $5 million for the nearly 20-year-old plane since the gas company was “hungry to sell, and that not very many people are in the market for 727s.”
He ended up paying $8 million for the plane, he wrote in the book.
Trump would also occasionally bring his aging parents on his personal plane, according to his former pilot, Mike Donovan.
“We’d carry Trump’s mother up the stairs and set her on a chair in the back of the plane,” Donovan told Vanity Fair in 2019. “Then we’d bring his father on board, too. And we’d sit on the tarmac for an hour and a half while Trump talked to his parents. His father couldn’t fly. We’d bring him down the ramp and put him in his car and then we’d take off for Florida carrying his mother with us.”
Though records show Trump briefly lost ownership of the aircraft when the Trump Shuttle collapsed, he reacquired it and it became a frequent sight in New York, West Palm Beach and on his TV show, “The Apprentice.”
“When I park this big, beautiful plane at the end of the runway at LaGuardia Airport, that’s all about advertising. People going out see the name Trump,” he told the season five “Apprentice” candidates in one episode from 2006. “If you learn to make a real lot of money, you can have a plane just like this someday.”
The plane flew for Trump until he upgraded to a larger Boeing 757 in 2011, a move the Palm Beach Post noted at the time raised speculation he might be considering a presidential run.
The Boeing 727 was sold to a Malaysian company that chartered it for VIP transport for a few years, before the aircraft was scrapped. Pieces of the plane’s skin were cut up and made into gold plated money clips, which a private company is selling for $195.
“Trump 727” money clips sport the plane’s tail number and “*45 | 47*” — denoting both of his terms in the White House.
Today, the Trump Organization’s private fleet of aircraft consists of the “crown jewel” Boeing 757 with a 3,000-mile range and Rolls Royce engines, which Trump has often touted.
According to the Trump Organization’s website, the custom plane features Italian leather seats embroidered with the Trump family crest, 24-karat gold-plated accents, two private guestrooms, three bathrooms, dining and conference areas and an entertainment system.
It was this plane, sometimes dubbed “Trump Force One,” that carried him across the country during his 2016 and 2024 presidential campaigns. It also occasionally served as a backdrop for rallies.
A person familiar with Trump’s plane told CNN the operations within the aircraft were always “time pressed” but “immaculate.”
“He was very detail-oriented, and he noticed it immediately,” the person said. “If it wasn’t right, wasn’t to his liking, we would be told immediately, but not forcefully, just that it needs to be fixed.”
By the end of Trump’s first term in office, the plane was grounded and had to be overhauled before it could fly again in 2022. CNN previously reported that its engines were undergoing repairs, and it sat idle in a New York airport while he was not using it.
It was repaired and flew Trump during his 2024 campaign to retake the White House.
Today, open-source flight tracking sites, including ADS-B Exchange, show it’s still flying but is mostly used by members of the first family, including his sons, Eric Trump and Donald Trump, Jr.
The president also previously owned a series of smaller aircraft, including Sikorsky S76 Helicopters, which he flew and “served as an exclusive amenity for our executives, members, and VIP guests,” according to the Trump Organization website.
“Each helicopter was outfitted with high-end comfortable interiors, refreshment centers, and live map displays,” the website read.
In 1997, Trump also bought a smaller jet, a Cessna Citation X, painted white with the Trump family crest on the fuselage.
The company described it as a “rocket in the sky,” flying at 92% of the speed of sound and with the ability to land at smaller airports that couldn’t handle the Boeing 757. The nine-passenger plane drew attention in 2016 when it continued to be flown after the FAA registration expired, CNN reported.
The registration issues were later resolved and the plane flew Trump when his Boeing 757 was being repaired or he needed to travel to small airports.
The Citation was sold in March of 2024 and purchased by a company connected to a Texas real estate developer and Republican donor, according to AIN, a business jet news publication.
The experiences with his personal planes would set the stage for navigating new presidential transport.
A new Air Force One
Presidents have been flying since Teddy Roosevelt took off in a Wright Brothers biplane on a campaign swing in 1910 and Franklin Roosevelt crossed the Atlantic in office on a flying boat during World War II.
After confusion over the flight numbers of Dwight Eisenhower’s plane and an Eastern Air Lines flight nearly caused a crash in 1953, the Air Force One callsign was established.
His successor, John F. Kennedy, flew the first jet specially built for presidential use, one of several modified presidential Boeing 707s, known as a VC-137s.
However, since President George H.W. Bush, US presidents have been primarily flying a pair of heavily modified Boeing 747-200s. These two planes are known as the Air Force’s VC-25As, which Trump flew for his first term and for the beginning of his second.
“We really had very little difficulty, but age was finally catching up to it no matter what we did,” Trump said Friday.
Now, three of the newest passenger variants of the jumbo jets, which stopped being built in 2023, are about to take over presidential transport.
The 747-800 was selected as the basis of the VC-25B, the new primary plane to serve as Air Force One in 2015, during the Barack Obama administration, as the old planes were expected to exceed their service lifetime in 2017.
After delays and cost overruns, Trump renegotiated the agreement during his first term in office. The new plan was to use two aircraft Boeing originally built for a Russian airline that went bankrupt before they could be delivered. Those planes were supposed to be completed for presidential use in 2022, but now are expected by 2028, the Air Force said.
“I’m not happy with the fact that it’s taken so long,” Trump told reporters aboard Air Force One last year. “There’s no excuse for it.”
A third Boeing 747-800 plane, donated to the US by the government of Qatar and heavily modified in Texas, was unveiled Friday. The donated jet was designed to bridge the gap until the other planes are ready.
“By making minimal changes to the previous head-of-state interior, the Air Force fielded the aircraft faster without accepting any risk regarding security, safety, or secure communications,” a senior administration official told CNN.
When the president announced he planned to accept the jet from Qatar, it raised a lot of eyebrows.
Several Republican senators expressed misgivings about the idea, pointing to the potential for security and legal risks. Trump’s plan for the plane to go to his presidential library after he left office also raised ethical concerns.
“I asked the emir if we could use the brand new 747… And I said we’d like to use it for a little while because the planes are pretty old,” Trump said Friday. “A normal president wouldn’t do this; a normal president wants to stay away from aircraft… but our country has to be represented properly.”
One of the most distinguishing features of the new planes are the colors painted on its exterior.
Trump steered away from the baby blue and white colors that Air Force One has sported since the Kennedy administration, opting for an entirely new livery.
“They said what color do you like? I said, I like the color of the American flag, right, that makes sense,” Trump said. “All of the planes in the fleet are being changed into this look, which is a much better look and a more appropriate look.”
Trump’s proposed change sparked speculation that he intended to replicate the colors of his personal Boeing 757, and some observers noted it resembled the paint jobs seen on past commercial planes.
Despite all of the hurdles, over a year after it was donated, the latest Air Force One jet is ready for the president.
“The workmanship of this plane is, when you see it, you won’t believe it,” Trump said at the plane’s unveiling. “Actually, the quality of woods, the quality of the materials, the quality of the engines. These engines are the finest; they’re the best in the world.”
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