Bar bets are a not-uncommon occurrence, but very few bar bets result in a plane landing in the middle of New York City. Unless, of course, you’re Thomas Fitzpatrick—who absconded with an aircraft and landed it in Upper Manhattan not just once, but twice.
Thomas Fitzpatrick’s aviation career doesn’t really have the same trajectory as famous pilots like Charles Lindbergh or Chuck Yeager. His brother says that at 15 years old, Fitzpatrick covered the truth about his age in order to join the Marine Corps during WWII. It was during this time that the New York native learned to fly, taking to the skies in a reconnaissance plane.
After the Marines discharged him, Fitzpatrick joined the Army and was in Japan when the Korean War broke out. During a rescue, he was wounded, making him the first New Yorker to sustain an injury in the conflict. He then received a Purple Heart. 
WikipediaWhen Fitzpatrick returned home, he found work as a steamfitter, a job that he stayed in for 51 years, settling in Emerson, NJ. Though Fitzpatrick later claimed he “never wanted to fly again,” his exploits say otherwise.
Late one night in September of 1956 after a few too many, Thomas Fitzpatrick made a bet. He told patrons at a bar in Washington Heights that he could fly from New Jersey to New York City in 15 minutes and they bet that he couldn’t. Fitzpatrick then went to Teterboro Airport and took a plane from the flight school. Refusing to use lights or radio, he completed the flight and landed it in front of the bar around 3am.
Though he’d won the bet, Fitzpatrick was now in big trouble—or at least, he should’ve been. Perhaps impressed by the stunt, the owner of the plane didn’t want to press charges. As a result, Fitzpatrick got away with a $100 fine and the New York Times saying it was “a feat of aeronautics” and that he’d made “a fine landing.”
There was just one thing: Fitzpatrick wasn’t done yet.
In 1958, at another bar in Washington Heights, Thomas Fitzpatrick retold the tale of his “Late Night Flight.” When someone at the bar challenged him on it, another bar bet was made….and Fitzpatrick returned to Teterboro again, with his friend from the bar in tow. He landed not far from where he had the first time and, perhaps quickly realizing that he was about to be in deep trouble, escaped into the night.
Of course, this time, the authorities knew exactly who to look for. When they picked him up, he blamed “the lousy drink.” A judge later sentenced Fitzpatrick to six months behind bars—an attempt to make up for the punishment he never received for his first flight.
Luckily for the folks at Teterboro Airport, Thomas Fitzpatrick hung up his pilot’s hat after two incredibly memorable and dangerous late night flights.
