Thomas Fitzpatrick and the stolen Piper that landed on a Manhattan street twice to win a bar bet

Thomas Fitzpatrick, a former Marine, twice stole a single-engine Piper from a New Jersey airfield and landed it on the streets of upper Manhattan to settle bar bets. The first landing occurred on Saint Nicholas Avenue in September 1956; the second on Amsterdam Avenue in 1958. Both landings happened in the early morning hours, without a flight plan, without clearance, and—by most accounts—without sobriety.

How Did a Stolen Airplane End Up on a Manhattan Street?

In late September 1956, Fitzpatrick was drinking at a bar in Washington Heights when an argument broke out over whether someone could get from New Jersey to upper Manhattan in fifteen minutes or less. Fitzpatrick didn’t just claim he could do it—he told the bar he’d land a plane on the street out front.

He left the bar and made his way to the Teterboro School of Aeronautics airfield in New Jersey. Airport security in 1956 was virtually nonexistent at small fields—no fences, no cameras, no TSA. Fitzpatrick found a single-engine Piper, most likely a J-3 Cub or PA-12 Super Cruiser depending on the source, and got it airborne.

He had some flight training—enough to take off from a dark field in the middle of the night. He flew east across the Hudson River with no flight plan, no radio communication, and no lights worth mentioning.

The First Landing: Saint Nicholas Avenue, 1956

Fitzpatrick flew a small, slow airplane over the most densely populated city on the continent, at night, with no clearance and no navigation aids. Washington Heights in 1956 was lined with apartment buildings, streetlights, and cars parked bumper to bumper along the curbs.

He found Saint Nicholas Avenue—a wide, straight street—and at roughly 3:00 a.m., set the Piper down on the pavement between parked cars. The street had manholes, potholes, and every other obstacle a New York road offers. He landed, parked the airplane on the street, and walked back into the bar.

He was arrested. The airplane’s owner pressed charges. But the judge reportedly couldn’t find a specific ordinance covering landing a stolen airplane on a city street. The grand larceny charge was eventually reduced, the owner declined to press the matter fully, and Fitzpatrick paid a fine of roughly $100.

The Second Landing: Amsterdam Avenue, 1958

Two years later, Fitzpatrick was back at a bar—possibly the same one—when someone questioned his story. The doubter said there was no way he’d actually landed a plane on Saint Nicholas Avenue.

Fitzpatrick went back to Teterboro, stole another Piper, and in the early morning hours flew it across the Hudson again. This time he landed on Amsterdam Avenue, just a few blocks from the original site in Washington Heights.

The court was less forgiving the second time. The magistrate reportedly told him: “Had I been the judge on the first case, you would not have been here for a second.” Fitzpatrick received a longer sentence—some accounts say six months. The FAA (which had just been renamed from the Civil Aeronautics Administration that same year) revoked whatever certificates he may have held.

What Made the Landings Possible?

Several factors aligned both times, any one of which could have turned the story into a tragedy:

Empty streets. Both landings happened around 3:00 a.m. when traffic was minimal.
Cooperative weather. No significant wind gusts to catch a wing on a parked car or fire escape.
The right airplane. A light taildragger like the J-3 Cub has a slow stall speed and short landing roll—about as forgiving as a fixed-wing aircraft gets for an improvised strip.
The pilot’s nerve. Fitzpatrick was a Marine who served in Korea. Whether his confidence came from genuine skill, combat-tested composure, or sheer recklessness is a matter of debate.

The margin for error on a street landing is almost zero. One car pulling out, one power line at the wrong height, one gust pushing a wingtip into a building, and the outcome would have been entirely different.

What Happened to Thomas Fitzpatrick?

After the second landing, Fitzpatrick reportedly settled into a quiet life. He raised a family and stayed out of cockpits—at least the stolen variety. He passed away in 2009 at the age of 79.

The story has been retold countless times, with details shifting across decades of retellings. The core facts remain consistent across historical accounts and New York newspaper archives: a Marine, a bar bet, and a stolen Piper on a Manhattan street. Twice.

Key Takeaways

Thomas Fitzpatrick stole a Piper from Teterboro and landed on a Manhattan street twice, in 1956 and 1958, to settle bar arguments.
Virtually nonexistent airport security at small 1950s airfields made the thefts possible—no fences, cameras, or modern access controls.
The first landing resulted in a ~$100 fine; the second brought jail time and certificate revocation after the FAA took a harder line.
Every possible variable broke in his favor both times—empty streets, calm winds, no mechanical failure—making the landings a case study in survivorship bias rather than skill to emulate.
Fitzpatrick lived to 79, proof that luck is a real factor in aviation, but never one to count on.