On September 30, 1956, Marine veteran and Purple Heart recipient Thomas Fitzpatrick
got into a friendly but alcohol-fueled spat with fellow patrons at a bar in Uptown Manhattan.
The argument ended with a bet that Fitzpatrick could not fly a plane from New Jersey to New
York in 15 minutes.
However, Fitzpatrick was determined — drunk or sober — to prove that he could.
As The Vintage News reported, Fitzpatrick left the bar and at approximately 3 a.m. stole
a single engine plane from the Teterboro School of Aeronautics in New Jersey.
He then proceeded to fly that plane without lights or radio communication back to the
bar where he made the bet.
He landed about 15 minutes later on St. Nicholas Avenue near 191st street.
The patrons were pretty impressed that Fitzpatrick was able to make good on his wager, and we
bet they were also a little scared of him by that point too.
"Supposedly, he planned on landing on the field at George Washington High School but
it wasn't lit up at night, so he had to land on St. Nicholas instead," Jim Clark,
a resident who saw the landing, stated.
"The New York Times called it a "fine landing" and a "feat of aeronautics."
For his illegal flight, he was fined a measly $100 after the plane's owner refused to
press charges because he was so impressed, the outlet reported.
However, fervor quickly died down and what was an amazing "hold my beer" moment,
turned into a story that most thought was fabricated.
Fitzpatrick continued to regale other bar patrons with the story of beating insurmountable
odds, but people just laughed him off, thinking it was an excuse for false bravado.
However, if it wasn't clear the first time, it was never a good idea to make a bet with
Fitzpatrick — because nearly two years later he proceeded to do the exact same thing to
prove his point.
On October 4, 1958, around 1 a.m., Fitzpatrick stole another plane from the same Teterboro
airfield — which apparently hadn't learned any lessons about improving security measures
after the first theft — and then landed on Amsterdam and 187th street "in front
of a Yeshiva University building after another bar patron disbelieved his first feat."
Well, this time people believed him.
He was a master at stealing planes and flying them into the city while intoxicated.
However, the city decided that Fitzpatrick needed a little time-out from making barroom
plane bets and hit him with a six-month prison stay.
John A. Mullen, the judge who sentenced him, claimed that if he had been punished properly
the first time, then he wouldn't have tried this again.
"Had you been properly jolted then, it's possible this would not have occurred a second
time."
For his feat of aeronautic excellence, the bar named a drink after him, calling it the
"Late Night Flight."
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