It sounds like something out of a movie—or maybe the wildest urban legend you’ve ever heard.
A man gets into a bar argument, says he can fly a plane from New Jersey to New York in under 15 minutes, and then actually does it.
Not once, but twice.
This isn’t fiction.
It’s the real story of Thomas Fitzpatrick, a decorated war veteran and skilled pilot who stunned New York City in the 1950s with two unbelievable—and illegal—landings right in the middle of Manhattan streets.
Who Was Thomas Fitzpatrick?
Born in 1930 in New York City, likely in the Washington Heights neighborhood of upper Manhattan, Thomas Fitzpatrick had already lived a remarkable life before his infamous flights.
He served in both World War II and the Korean War—first as a Marine, later in the Army.
He was even wounded in Korea and received a Purple Heart.
But returning to civilian life didn’t slow him down.
After his military service, he trained to become a pilot and worked as an airplane mechanic.
He studied at the Teterboro School of Aeronautics in New Jersey.
Fitzpatrick was known for being adventurous—even a little reckless—and his friends described him as someone with a “crazy side.”
That “crazy side” would soon make headlines.
The First Flight: A Bet, a Bar, and a Bold Landing
It all started on the night of September 30, 1956.
Fitzpatrick had been out celebrating with friends at a bar in Washington Heights. During a few rounds of drinks, he reportedly got into a heated debate.
Someone said it was impossible to get from New Jersey to Manhattan in under 15 minutes.
Challenge accepted.
At around 3 a.m., Fitzpatrick drove across the Hudson River to Teterboro Airport in New Jersey.
He knew the place well—it’s where he’d trained—and he “borrowed” a two-seater Cessna 140. Without permission. Without lights. Without radio communication. And, yes, while intoxicated.
He then flew the plane through the dark skies of New York and made a jaw-dropping landing on St. Nicholas Avenue, near 191st Street.
It was a narrow street, surrounded by buildings and parked cars.
According to one witness, he had originally planned to land on the field at nearby George Washington High School, but it was too dark.
The sight the next morning was surreal: a small airplane parked like a car on a city street.
People couldn’t believe their eyes. Was this a prank? A movie shoot? A dream?
Nope. It was very real.
Even the police were shocked.
Fitzpatrick at first claimed he had engine trouble, but investigators weren’t buying it.
The plane showed no signs of mechanical issues, and the fact that he’d taken off from and landed right near the same bar? Suspicious, to say the least.
Still, the owner of the plane declined to press charges.
Fitzpatrick ended up paying a $100 fine for violating city codes that prohibit landing planes on public streets.
That was it.
The press, meanwhile, couldn’t get enough.
The story made the front page of the New York Daily News.
Reporters, neighbors, and even police officers described the stunt as a near-impossible feat of precision flying.
Sgt. Harold Behrens of the police aviation bureau said the odds of pulling off such a landing were about 100,000 to 1.
Two Years Later, He Did It Again
You’d think that would be enough excitement for one lifetime. But Fitzpatrick wasn’t done.
Fast forward to October 5, 1958. He’s in another Manhattan bar, retelling the story of his legendary flight.
But one drinking buddy—a man from Connecticut—refuses to believe him.
So what does Fitzpatrick do?
He gets behind the wheel again and drives to Teterboro Airport.
There, he finds another plane—a red-and-cream Cessna 120.
Once again, he takes off without permission and heads for Manhattan. This time, he lands on Amsterdam Avenue near 187th Street, just a few blocks from his first stunt.
Locals couldn’t believe their eyes as the plane touched down—just feet away from cars and buses
A carpenter named John Johnson had to slam on the brakes to avoid getting hit.
A bus driver, Harvey Roffe, was so startled that he ducked inside his parked vehicle, thinking the plane might crash into the roof.
Unlike the first time, Fitzpatrick didn’t hang around to pose for pictures.
He quietly walked away but later turned himself in at the local police station. When asked why he did it again, his response was simple: “It’s the lousy drink.”
But this time, the consequences were more serious.
Jail Time and a Judge’s Warning
Fitzpatrick didn’t have a valid pilot’s license anymore—it had been suspended after his first stunt.
So when he landed the second time, he faced a long list of charges: grand larceny, flying without a license, reckless operation of a plane, and violating civil aviation laws.
At the hearing, the judge wasn’t impressed by Fitzpatrick’s repeat performance.
“Had you been properly jolted [the first time], it’s possible this would not have occurred a second time,” Judge John A. Mullen remarked.
This time, Fitzpatrick was sentenced to six months in jail.
The Legend Lives On
Despite the legal trouble, Fitzpatrick’s aerial stunts became part of New York City folklore.
In a city full of unbelievable stories, this one still stands out. It’s been called “the original ‘hold my beer’ moment.” But it’s also a reminder of how close genius and recklessness can be.
The truth is, Fitzpatrick was an incredibly skilled pilot.
Even the police and aviation experts admitted that pulling off two precision landings on narrow Manhattan streets was no small feat.
But there’s no denying it was dangerous—not just for himself, but for everyone below.
And yet, his story still sparks a kind of awed disbelief. Could someone really do that? Twice?
Yes. And Thomas Fitzpatrick did.
Life After the Headlines
After his jail time, Fitzpatrick eventually settled down.
He worked as a steamfitter for over 50 years, married his wife Helen, and raised three sons in New Jersey.
He passed away in 2009 at the age of 79.
His daring stunts live on as a bizarre, bold chapter in the history of New York City—a time when one man turned the streets of Manhattan into his own personal runway. Twice.
And while aviation security today makes sure this will never happen again, the legend of Thomas Fitzpatrick is likely to keep flying high.
