How many shots of beer would it take before you accept a bet that you can fly a plane back and forth in 15 minutes, ideally, while saying, “Hold my beer”? For American pilot Tommy Fitzpatrick, not so much. While pilots sometimes run into emergency situations that require them to come up with creative, if not risky, landing plans, his was definitely voluntary. If anything, he did so with a wide grin across his face. Not only that, he did it not only once but twice.

Meet Our Guy, Tommy Fitz

Born on April 24, 1930, in Washington Heights, Manhattan, New York, Thomas Edward Fitzpatrick first braved the wars of the past before he boldly pulled off his amazing stunt in September 1956. Fitzpatrick served and joined the US Marine Corps during World War II by enlisting and lying about his age, which was 15 at that time. He was stationed in China when he fought at the Pacific Theatre. A few years later, he reenlisted and joined the army on the battlefield of the Korean War. It was there where his buddies began calling him Tommy Fitz, and it was also there where he showed his boldness and bravery that he received his Silver Star and the the Purple Heart.

This was his citation:

“During a strategic withdrawal, Corporal Fitzpatrick noticed a wounded officer, about 100 yards forward of his position. In attempting a rescue, he and a companion were seriously wounded. Cpl. Fitzpatrick — despite severe pain and loss of blood — made it back to safety, directed a second successful rescue party, organized and provided covering fire to support the rescue.”

He was honorably discharged and exited Korea in 1952 and returned home as a war hero and veteran at the age of 26. Back home, he started working at a construction firm as a licensed steamfitter and, at the same time, took his time to pursue his love for flying by taking flying lessons at the Teterboro School of Aeronautics. However, there were some reports that he actually worked there as an aircraft mechanic and a trainee pilot.

Drunk Flying

There’s drunk driving, and then there’s drunk flying.

It was September 29, 1956, when Tommy Fitz and his co-workers from the construction firm were drinking at a local bar called Joe’s Bar on 191st Street, Manhattan. They had just attended a friend’s bachelor party, and they were not done celebrating yet. So, they went. They got the drinks and the conversation flowing, and they’re definitely having a great time. One of the patrons asked, is it possible to fly from New Jersey to Washington Heights in under fifteen minutes?

Tommy didn’t hesitate and answered yes, and was met with reactions of doubts. Challenge accepted. Tommy bet a drink that he could do it and the bet was accepted. Tommy left the bar in a somewhat inebriated state vowing to return.

The next thing the bar-goers knew, a red and white Cessna descended from the skies, landing on St Nicholas Avenue and taxied to a stop outside the bar. The pilot? No one else but Fitz. How he managed to sneak into the Teterboro Airport and steal the plane was a mystery. However, we know that he did so without establishing any radio communication and obtaining any mandatory flight clearance. He succeeded in traveling back and forth in fifteen minutes as he promised, weaving his way through New York skyscrapers. Initially, he was planning to land on a school playground, but he couldn’t see clearly, so he opted to touchdown on St. Nicholas Avenue near 191st Street. It was 3 am, and the bar was about to close, so he rushed in to get his final drink, hopefully, paid by the patron he challenged earlier.

The First time Thomas landed aircraft on the streets of Manhattan. (mdig/Medium)

The Police showed up and weren’t really sure what to do. No one had ever thought to put a law on the books making it illegal to land a plane on a New York City street, and stealing an airplane in New Jersey certainly broke the law in that state but they had no jurisdiction to arrest him for it in New York. Probably fearing Tommy would try to take off in the plane and leave again, the police charged and arrested him for illegal parking. As Judge Edward J. Chapman said, “A great many terrible things could have happened” setting his bail at $5,000 “as a deterrent to other foolish young men who get drunk and fly a plane..” Given Tommy’s otherwise good reputation and status as a war hero The judge decided to just impose a fine of $100 and got Tommy’s pilot’s license suspended for six months.  He could have been charged with grand larceny in New Jersey but the owner refused to press charges against the now locally famous dare-devil.

A newspaper clipping covering the bizarre incident. (

In court, Tommy Fitz was contrite and apologetic for his actions leaving the judge with the impression that he had learned his lesson and return to a normal life.  Tom appeared to settle down, getting married in 1958 and sticking with his job as a Steamfitter in the local union.

And then one night at another bar in New York city.

Drunk Flying Deja Vu

It had been nearly two years to the day since he pulled off his one in a million flying stunt,  In a loud, boisterous conversation it recalled that the anniversary date of his famous feat of aerial daring-do was almost upon them. While one of his friends narrated the events of that night, one of the bartenders serving them had the unmitigated gall to suggest that Tommy wasn’t the guy who actually did the deed.

No way, he was the same guy. The bartender was sure of it.

Well, you can just about guess what happened next. Rather than just forget it, or pull an old newspaper clipping out his wallet as proof, Tommy left the bar and went to Teterboro airport, again.

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The aircraft that Thomas stole the second time. (

Once again, Tommy committed an act of air piracy and stole an airplane.  Once again, he thread his way through Manhatten skyscrapers drunk as a Lord. Once again, he managed to land the plane safely near the bar in the dead of night.

Once again, he was arrested.

Except for this time, the judge threw the book at him and it wasn’t a flight manual, Judge John A. Mullen may have been surprised to see Tommy back in front of him, but this time he was not inclined to be charitable to him, “You’re not going to make an airstrip out of a New York City street,” he told him and Tommy found himself “grounded” for six months.  Not just from flying, but from anything.

He was going to jail.

After his release, Tommy was not only clean and sober but also a reformed man.  He returned to his wife and career as a steamfitter and lived to the ripe old age of 79, passing away in September 2009. He seemed a refutation of the old saying that “There are Bold pilots and there are Old pilots, but there are no Old, Bold pilots.”

In a rather fitting tribute, bars in the Washington Heights neighborhood in Manhattan that Tommy turned into an airport twice still offer a drink named for him, it’s called the “Late Night Flight.”