Tommy Fitzpatrick stole a plane from a New Jersey airport and landed it on St. Nicholas Avenue in northern Manhattan, right in front of the bar where he had been drinking around 3 a.m. on Sept. 30, 1956, when he was 26. He took a single-engine plane from the Teterboro School of Aeronautics in New Jersey and took off without lights or radio contact and landed on St. Nicholas Avenue near 191st Street. It was reported as a “fine landing” by the New York Times.
It would provide enough material to tell everyone and anyone "Remember the time when Fitz landed that plane outside?" Naturally, people wouldn't believe he did it. So he did again two years later to prove it. Both daredevil landings were made in incredibly narrow areas, in the dark – and after quite a number of drinks.
On Oct. 4, 1958, just before 1 a.m. Fitzpatrick made his second drink and land.
He took a plane from Teterboro once again but this time landed on Amsterdam and 187th Street in front of a University building. He apparently jumped out of the plane and fled the scene but decided to turn himself in afterwards. Fitzpatrick simply told the police that he did it the second time because someone at the bar refused to believe he had done it the first time around.
After that first time, Fitzpatrick was charged with grand larceny but that was then dropped as the plane’s owner declined to sign a complaint. In the end he was only charged $100 for violating the city’s administrative code, which prohibits landing a plane on the street.
But for the second time he did it, he was sentenced to six months in jail for bringing a stolen item into the city.
http://www.theladbible.com/articles/a-pilot-once-landed-a-plane-outside-the-bar-he-was-drinking-at-twice-for-a-bet
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