Thomas Fitzpatrick was in a tavern in Washington Heights, New York, in September of 1956 when a bet was proposed. Not one to turn down a bet, especially while drinking, Fitzpatrick obliged. The challenge? Get back to the bar from New Jersey in under fifteen minutes. He stole a plane from an airport in New Jersey and flew it into Manhattan, landing on the same street as the bar he had been at, St. Nicholas Avenue. Fitzpatrick took the plane from the Teterboro School of Aeronautics, and flew without radio communication or lighting. The story goes that he had planned on landing on the field at a local high school, but the lights were off, so he opted to land right on the street instead.
As if this feat wasn’t impressive—or terrifying—enough, Thomas Fitzpatrick did the exact same thing two years later. After a fellow bar patron said that he didn’t believe Fitzpatrick had ever pulled off the stunt, he set off to prove him wrong. This time, he took a plane from Teterboro and landed on 187th and Amsterdam, in front of a school building. After the first incident, he was charged with grand larceny, but the charges were dropped when the owner of the plane opted not to sign a complaint. Once he stole a plane a second time, Fitzpatrick was sentenced to six months in jail on the charge of bringing a stolen item into New York City.
Fitzpatrick was also charged with violating a city code that prohibits the landing of planes on a city street. For this violation, he was only given a fine of $100. Despite the risk he took, people who witnessed the stunt said that Fitzpatrick was a phenomenal flier. After all, he had to be, to land an airplane in the streets of New York City, with cars, lampposts, and people nearby, without harming anyone.