Tommy Fitzpatrick Landed a Stolen Plane in Manhattan Twice

Most pilots would consider landing a small airplane on a narrow Manhattan street almost impossible. Thomas “Tommy” Fitzpatrick did it not once, but twice.

The decorated veteran did the daring maneuver both times from an airport in New Jersey to Washington Heights, dodging buildings, streetlights, and parked cars before he managed to land on the city pavement.

He had no authorization for either flight; he stole the aircraft both times, and alcohol was the main instigator in both of his joyrides. The first one happened because of a drunken bet, while the second one was a reminder to prove that he actually had achieved the impossible.

A Veteran with a Wild Side

Fitzpatrick was more than a neighborhood daredevil. According to his obituary, he served in the Marine Corps in the Pacific during World War II. After leaving the Marines, he joined the U.S. Army and served during the Korean War, where he was wounded and received the Purple Heart.

After his decorated service, he lived in New Jersey and worked as a steamfitter for nearly 51 years. He was described as a hardy man who enjoyed the riskier parts of life. That personality then entrenched itself in aviation history in 1956, when he gave New York City an interesting night.

Bets That Naturally Lead to Stolen Planes

At a tavern in the morning of Sept. 30, 1956, Fitzpatrick was drinking at a Washington Heights tavern when someone didn’t believe that he could travel from New Jersey to the neighborhood in 15 minutes. This prompted Fitzpatrick to accept the bet.

The 26-year-old traveled to the Teterboro School of Aeronautics in N.J., took a single-engine airplane and departed without lights or radio contact. He flew across the Hudson River toward Manhattan at approximately 3 a.m.

He planned to land at a local high school but found that it was too dark outside to properly land the aircraft. He then landed it near the bar on 191^st Street, concluding the joyride.

The street was littered with all manner of things to hit. Buildings, lampposts, and cars were just a few of these items. He managed to land without striking anything or anyone, to the surprise of all his friends. The New York Times later talked about the landing in an incredulous way.

As is only natural when someone steals an airplane, Fitzpatrick was arrested on suspicion of grand larceny. The owner of the aircraft didn’t press charges, and the only trouble facing him was a fine.

The Fine Wasn’t Enough

For most people, a brush with the law and a fine is considered quite a penalty. For Fitzpatrick, he wanted to do the adventure again. On Oct. 4, 1958, a patron at another Washington Heights bar reportedly challenged Fitzpatrick’s story and refused to believe he had landed an airplane on a Manhattan street.

This was all he needed, and then he decided to take a single-engine airplane without permission again. The time was shortly after midnight, and he flew into Manhattan and landed near Amsterdam Avenue and 187th Street, this time in front of a Yeshiva University building.

Those who saw the daring flights said that Fitzpatrick climbed out of the airplane before fleeing the scene. Instead of being arrested, he decided to turn himself in.

This time, he didn’t get a simple fine. The court convicted him of bringing stolen property into the city and sentenced him to six months in jail. The judge understandably thought that a stronger first sentence would have avoided a second landing.

No Third Strike Needed

Fitzpatrick learned from his mistake, and he never renewed his pilot’s license. He died in 2009 at age 79, leaving behind a story that sounds more like a Hollywood comedy than an actual episode in New York history.

These kinds of daring stunts are reckless, illegal, and dangerous for all involved. For Fitzpatrick, he cemented his infamy in New York, challenging those who dared him the first and second time. Dodging buildings and cars with 1950s air technology, he made sure that no one could ever call him a liar.