Thomas Fitzpatrick Story

Thomas Fitzpatrick: The Amateur Pilot Who Drunkenly Landed A Plane On An NYC Street — Twice

Published November 19, 2019
Updated July 25, 2022

On a barroom bet, Thomas Fitzpatrick landed a plane on a Manhattan street. And when another drinking companion later claimed that landing never happened, Fitzpatrick did it again.

In 1956, a World War II veteran-turned-airplane pilot named Thomas Fitzpatrick did what seems totally unthinkable: He flew a single-engine plane through the urban canyons of New York City and landed it perfectly on an uptown Manhattan street — all because of a drunken bet.

Thomas Fitzpatrick

The New York Daily NewsThomas Fitzpatrick made the front page of newspapers after he landed a plane in the middle of New York City — twice.

Then, two years later, he did it again.

Thomas Fitzpatrick’s Early Life

Very little is known about Thomas Fitzpatrick, but from what is known it seems he lived a very colorful life even before landing airplanes on New York City streets.

Early Washington Heights

Frank M. Ingalls/The New York Historical Society/Getty ImagesA view of Washington Heights, where Thomas Fitzpatrick grew up, in the early 1910s.

Thomas Fitzpatrick was born in New York City in 1930, possibly in the upper Manhattan neighborhood of Washington Heights. He served in the U.S. Marine Corps in the Pacific Theater of World War II, though where exactly in the Pacific isn’t known.

After he was honorably discharged from the Marines, instead of leaving the military life behind, Fitzpatrick joined the U.S. Army, where he served in the Korean War. Wounded during the fighting, he received a Purple Heart and finished out the war with the Army, eventually returning to civilian life after his term of service. However, he was known to be a restless soul.

“Tommy had a crazy side,” said Fred Hartling, an old neighbor of Fitzpatrick’s who talked about the young pilot’s early antics in the New York Times. Hartling’s brother, Pat, was good friends with Fitzpatrick, and Hartling said the two were part of “a wild bunch” of friends.

Teterboro School Of Aeronautics

Vintage Bergen County/FacebookAfter retiring from the Army, Thomas Fitzpatrick enrolled in flying school at the Teterboro School of Aeronautics.

At some point, Thomas Fitzpatrick became interested in being a pilot and he enrolled in flying school at the Teterboro School of Aeronautics in New Jersey. By the time he was 26, Fitzpatrick was working as an airplane mechanic.

Thomas Fitzpatrick’s First Manhattan Landing

Thomas Fitzpatrick's Plane Parked In Manhattan

The New York TimesThomas Fitzpatrick landed a single-engine Cessna 140 on St. Nicholas Ave near 191st Street.

On September 30, 1956, after having a few drinks at a local tavern in Washington Heights, Thomas Fitzpatrick drove to his flying school, “borrowed” one of their single-engine planes, and flew it back to the St. Nicholas Avenue bar where he had been drinking earlier that evening.

Reportedly, Fitzpatrick tried to first land the plane in a nearby park but found it was too dark to see, so he opted for the street instead. He made a drunken precision landing at around 3 a.m. on St. Nicholas Avenue near 191st Street.

When residents awoke, they were amazed to find a small plane parked in the middle of the city streets. According to resident Jim Clarke, who spoke of seeing the plane near his home, Fitzpatrick had planned to land on the field at George Washington High School — not on the street — but it was too dark to do it.

“The story goes, he had made a bet with someone in the bar that he could be back in the Heights from New Jersey in 15 minutes,” Clarke said. The successful impromptu landing made the front pages of local news outlets like the New York Daily News and the Democrat and Chronicle.

Another resident, Sam Garcia, was just a kid when he saw Thomas Fitzpatrick’s plane in the middle of New York City. The sight of an airplane in the middle of the street was so unexpected that he didn’t believe it was real.

Washington Heights

Google MapsThe Manhattan intersection where Fitzpatrick made his first city landing, as it is today.

“I thought maybe they had trucked it in, as a practical joke, because there was no way a man had landed in that narrow street,” Garcia recalled.

Despite the danger Thomas Fitzpatrick could have caused with his aerial stunt, it was hard to deny he had performed a near-impossible landing, flying through a narrow public street boxed in by high buildings, cars, and lamp posts. The New York Times sang his praises, calling it “a feat of aeronautics.”

In fact, even the police were impressed, despite their suspicions against the pilot’s claims that he landed the plane in the street due to engine trouble (Fitzpatrick later admitted in an interview that he had done it as part of a bar bet). Sgt. Harold Behrens of the police aviation bureau said the odds against sticking a landing like that were 100,000-to-1.

Two Years Later, He Did It Again

Thomas Fitzpatrick's Plane

Democrat and ChronicleWhen Thomas Fitzpatrick landed in NYC the second time, he tried to deny he was the culprit until several witnesses identified him as the pilot.

But that was not the last of the daredevil pilot. On Oct. 5, 1958 — just two years after his first aerial stunt — Thomas Fitzpatrick landed another aircraft on a Manhattan street, this time a red-and-cream single-engine Cessna 120 on Amsterdam Ave near 187th Street.

Just like the first time, Fitzpatrick flew the plane smoothly onto the streets of the city, as if it were an aircraft tarmac.

He had performed his second aerial stunt after an unknown man from Connecticut didn’t believe Fitzpatrick’s story about his first Manhattan landing, though the alcohol he’d been consuming certainly played a role.

“It’s the lousy drink,” he told the New York Daily News at the time. Unfortunately for Fitzpatrick, he performed this landing without a valid flying permit and admitted to investigators that he hadn’t renewed his pilot’s license after it was suspended following his first stunt.

“I never wanted to fly again,” he said, but fly he did, if only to prove his new drinking buddy wrong. He said they drove together to Teterboro, where Fitzpatrick picked up the single-engine plane that was sitting on the tarmac.

This time, however, several witnesses saw his daredevil landing up-close. John Johnson, a local carpenter, was riding his motorcycle in the streets just before he had to pump on the brakes to avoid colliding with Fitzpatrick’s plane.

Thomas Fitzpatrick In The News

Democrat and ChronicleThe inspiration for both aerial stunts began in bars in the Washington Heights area.

Another eyewitness was bus driver Harvey Roffe, who was sitting in his parked bus when Fitzpatrick flew right over. He instinctively dove to the floor, afraid that the plane was going to tear open the top of his bus.

“What the hell could you say if they ever pulled you in on a safety hearing for having an accident with an airplane?” Roffe told a reporter afterward.

Unlike the first time, though, Thomas Fitzpatrick fled the scene once he had landed. He later turned himself in at the Wadsworth Ave police station, shamelessly telling officers he “just happened to be in the neighborhood” and heard that police wished to speak with him.

Both Stunts Landed Him In Hot Water

Cessna 140 Plane Model

Wikimedia CommonsThe Cessna 120 and 140 models were the first aircrafts produced right after World War II.

Thomas Fitzpatrick’s impressively precise landings went down in history as some of the wildest drunken stunts to ever happen in New York City, but that doesn’t mean there weren’t consequences. As impressed as the police investigators were with his skill — Fitzpatrick himself acknowledged that he was “one hell of a pilot” — others were less enthusiastic about the repeat offense.

After his first Manhattan landing in 1956, Fitzpatrick was charged with grand larceny and for violating the city’s administrative codes, which prohibited planes from landing on city streets. The owner of the plane declined to press charges on the larceny, so the first charge was dropped and he was only fined $100.

He didn’t get as lucky the second time around, though. It likely didn’t help that he tried to deny that he was the pilot who landed the plane on the street, only confessing after several witnesses identified him as the plane’s pilot. At his arraignment hearing in 1958, the magistrate said that Fitzpatrick had “come down like a marauder from the skies.”

Second Fitzpatrick Plane Landing

Google MapsSomewhere between Amsterdam Ave and 187th Street, where he landed the second time.

After his second landing, Thomas Fitzpatrick was charged with grand larceny, dangerous and reckless operation of a plane, making an unauthorized landing in city limits, and violation of Civil Aeronautics Administration regulations for flying without a valid license. Judge John A. Mullen sentenced him to six months in jail for bringing the stolen plane into the city.

“Had you been properly jolted [the first time],” Mullen remarked during Fitzpatrick’s sentencing, “it’s possible this would not have occurred a second time.”

Criminality aside and despite the damage that Thomas Fitzpatrick’s stunts could have caused, his superb flying capabilities were still what everyone wanted to talk about.

“It was a wonder – you had to be a great flier to put that thing down so close to everything,” said Hartling. Mostly forgotten amid the long and extensive history of New York City, Fitzpatrick’s stunts have yet to be matched, and given the extent of aviation security around the city after the September 11th terrorist attacks, they likely never will be.

As for Thomas Fitzpatrick himself, he worked as a steamfitter for 51 years, settling down with his wife, Helen, and their three sons in Washington Township, New Jersey. He died on September 14, 2009, at the age of 79.

Now that you’ve caught up on the story of Thomas Fitzpatrick’s two drunken landings on the streets of New York City, witness the horrifying death of tightrope walker Karl Wallenda, then, meet Richard Bong, America’s best fighter pilot of World War II who downed 40 planes before dying in a simple training mission.

Natasha Ishak
A former staff writer for All That's Interesting, Natasha Ishak holds a Master's in journalism from Emerson College and her work has appeared in VICE, Insider, Vox, and Harvard's Nieman Lab.
Jaclyn Anglis
Jaclyn is the senior managing editor at All That's Interesting. She holds a Master's degree in journalism from the City University of New York and a Bachelor's degree in English writing and history (double major) from DePauw University. She is interested in American history, true crime, modern history, pop culture, and science.
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Ishak, Natasha. "Thomas Fitzpatrick: The Amateur Pilot Who Drunkenly Landed A Plane On An NYC Street — Twice.", November 19, 2019, Accessed May 21, 2024.