Drunken bets have, throughout history, caused the most inconceivable events. Some become intertwined with urban myths, as the results were simply too crazy to believe. One such crazy bet that took place in New York City in the 1950s was well-documented by the authorities.

The story of Thomas Fitzpatrick, the pilot who stole an airplane twice just to win a bet, remains one of New York’s favorite feats. Fitzpatrick, nicknamed Thomy Fitz, even earned a cocktail being named after him―the Late Night Flight.

This patron saint of drunken adventures gained popularity on September 30, 1956, when he decided to break into the Teterboro School of Aeronautics and steal a light aircraft. As mentioned, the motive for the theft was a bet placed in a New York City bar. Fitzpatrick claimed that he could make the trip from New Jersey to New York in less than 15 minutes.

Of course, he didn’t mention that he intended to use an aircraft as his mean of transport. The bet was on, as everyone in their right mind was convinced that Fitzpatrick was simply too drunk to comprehend the notion of time at that moment.

Well, he certainly was drunk―very drunk, for that matter―but he also had an ace up his liqueur-stained sleeve. He took off around 3 A.M., without any lights and keeping his radio silent. According to one of Fitzpatrick’s contemporaries, his original plan was to land at the field of George Washington High School, but since the lights surrounding the field were not switched on that night, Thomy Fitz quickly decided on a far more dangerous option.

This daredevil eventually landed directly on a Manhattan street, avoiding street-light poles and parked cars alike. He glided between the buildings, landing on St. Nicholas Avenue and parking his airplane right next to the bar in which the bet was placed earlier that day. All of that in less than 15 minutes. All of that drunk.

This making of a legend was certainly noticed by the police, who stood in awe before the unusual scene: an airplane parked in front of a bar in the middle of the street. Thomas Fitzpatrick was arrested and later fined $100 (equivalent to today’s $800) but was soon released, after the owner of the airplane decided not to press charges against him.

The owner was rather amused by the event, and since the airplane was returned in perfect condition, he saw no purpose in bringing Fitz to court. The fine was issued for violating the city’s administrative code, which prohibits landing a plane on the street, naturally.

Now, this was apparently all perceived as a laughing matter, and Thomas Fitzpatrick was celebrated in the newspapers as his flight was dubbed a “feat of aeronautics” accompanied by a “fine landing.”

However, two years later, in 1958, the restless pilot was once again challenged, as some doubted the credibility of his story. Well, “Hold my beer,” he must have uttered at that moment, for he was ready to go through it all over again.

On October 4, he repeated the stunt, stealing another plane from the same school of aeronautics.

This time he landed at the intersection of Amsterdam and 187th street, right in front of a Yeshiva University building. The flight was once again conducted in the dead of night, just before 1 am. Once again, his landing was miraculous―as one other contemporary of the event, Sam Garcia, told the New York Times in 2013: “I thought maybe they had trucked it in, as a practical joke, because there was no way a man had landed in that narrow street“.

After the repeated incident, the cities authorities weren’t so entertained. Judge John A. Mullen sentenced Fitzpatrick to six months in jail. After pronouncing the sentence, Judge Mullen told the pilot, with a tone of a disappointed parent: “Had you been properly jolted then, it’s possible this would not have occurred a second time.”

Fitzpatrick, obviously struck by his sentence, simply replied, explaining the cause of his mishaps: “It’s the lousy drink.”

Many years after the event, in an article in the New York Times, residents told the story of Tommy Fitz, with a Mr. Garcia stating: “If it happened today, they would call him a terrorist, and locked him up and thrown away the key.”

Related story from us: The first police car was bought in Akron, Ohio in 1899; its first assignment was to pick up a drunk man

Jokes aside, the airplane stunt was certainly an act of a reckless man, but since no one was harmed, the story became a testimony of the eccentricity of New Yorkers.

As for Fitz, he led a fulfilled life until 2009, when he died of cancer, aged 79. As a veteran of WWII, he had joined the Army once more during the Korean War and earned a Purple Heart for his service. Tommy Fitz was also a family man, leaving behind him three sons to tell the tale of his daring accomplishments.