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Tommy Fitzpatrick
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While drinking, a pilot bet he could land outside the bar, 2 hours later he touched down in central New York in a stolen aircraft. Years latter he repeated the stunt because someone wouldn’t believe him.

It was on September 30, 1956 and New Jersey resident Thomas Fitzpatrick was visiting pals in his old stomping grounds of Washington Heights, in New York City. After a few drinks at a bar, the story goes someone proposed a bet that Fitzpatrick couldn’t get from Jersey to the Heights in 15 minutes.
Apparently, when he returned to Jersey that night, the challenge still stuck in his craw. So at around 3 a.m. he snuck into a single-engine plane at the Teterboro School of Aeronautics. Then, fortified by the courage that earned him a Purple Heart during the Korean War – and also maybe by beer — he flew the thing back to the Big Apple. Nailing a perfect landing on St. Nicholas Avenue near 191st Street in front of the bar in which the bet was placed earlier that day.

The New York Times called it a “fine landing” and reported that it had been widely called “a feat of aeronautics.” In that gentler era, Thomas was hailed not as a threat to society, but a minor hero. The plane’s owner refused to press charges. So instead of going to jail for grand larceny, Thomas’s only punishment was a hundred dollar fine. Which might explain why, two years later, he did it again.

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