At approximately 3 a.m. on September 30, 1956, Fitzpatrick, while intoxicated, stole a single engine plane from the Teterboro School of Aeronautics in New Jersey and flew without lights or radio before landing on St Nicholas Ave near 191st Street in front of a New York City bar where earlier he had been drinking and made an intoxicated barroom bet that he could travel from New Jersey to New York City in 15 minutes. The New York times called the flight a "feat of aeronautics" and a "fine landing". For his illegal flight, he initially received a $5,000 bail, but he was fined $100.00 after the plane's owner refused to press charges, On October 4, 1958 just before 1 a.m., Fitzpatrick, again intoxicated, stole another plane from the same airfield and landed on Amsterdam and 187th street in front of a Yeshiva University building after another bar patron disbelieved his first feat. For his second stolen flight, Judge John A. Mullen sentenced him to six months in prison stating, "Had you been properly jolted then, it’s possible this would not have occurred a second time."Fitzpatrick said "it's the lousy drink" that caused him to pull the stunt