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The Wild Flights of Thomas Fitzpatrick: From Bar Bet to Urban Legend


When most people have a drink or two, they might wager on a game of darts, or perhaps boast a little about their past. But for Thomas Fitzpatrick, an evening in a bar in 1956 led to an unexpected night flight—and ultimately, a legend that spanned decades.


The Bet That Took Flight

In the early hours of September 30, 1956, Thomas Fitzpatrick, a New Jersey steamfitter and former Marine, had already spent a good chunk of the evening at a bar in New York City. As the conversation grew bolder and the bets wilder, Fitzpatrick found himself at the centre of a challenge: could he travel from New Jersey to New York City in just 15 minutes? For most, this would have been a harmless boast or an impossible proposition, but Fitzpatrick took the dare as a call to action.


Without a second thought—or perhaps one too many—he made his way to Teterboro Airport in New Jersey, a small airport known for flight schools and private planes. Here, Fitzpatrick, evidently unbothered by notions of legality or basic safety, helped himself to a single-engine plane. Under normal conditions, even the most experienced pilot would exercise caution, especially in the dead of night without lights or a radio. But Fitzpatrick, by all accounts, flew with an enviable combination of skill and sheer nerve, navigating the dark skies above New Jersey and New York.



A “Fine Landing” on St. Nicholas Avenue

The New York Times would later call it a “feat of aeronautics” and praise his “fine landing”—and it wasn’t hyperbole. Fitzpatrick successfully touched down on St. Nicholas Avenue, directly in front of the bar where his wager had originated. With an audience likely gobsmacked by his unexpected return, Fitzpatrick had completed his 15-minute journey from New Jersey to New York City in about the most memorable way possible. His landing on the narrow avenue, in pitch darkness, showed a skill most pilots would have struggled to replicate even under ideal conditions.

plane sat on 191st Street in 1956 after its wings were removed for shipment. The pilot landed the craft on St. Nicholas Avenue, rear, as part of a barroom bet.

Despite the audacity (or perhaps because of it), Fitzpatrick avoided serious repercussions. The plane’s owner declined to press charges, leaving Fitzpatrick with nothing more than a $100 fine—about $1,120 today. It was a slap on the wrist for what was, without a doubt, a highly illegal stunt.


The Second Flight and Six Months Behind Bars

Most people might have counted themselves lucky and left it at that. But two years later, Fitzpatrick found himself in another bar, likely recounting his story with a hint of swagger. The problem was that one of the patrons didn’t believe him. Stubborn pride—or, as Fitzpatrick himself would later blame, “the lousy drink”—kicked in, and he took the challenge to prove his claim. Once again, he headed to Teterboro Airport, commandeered a plane, and took to the night skies.


This time, he aimed to land near Amsterdam Avenue and 187th Street, not far from Yeshiva University. The police were less forgiving than before, and Fitzpatrick’s second stunt landed him in front of Judge John A. Mullen. This time, the judge wasn’t content with a fine. As he handed down a six-month prison sentence, Judge Mullen commented, “Had you been properly jolted then, it’s possible this would not have occurred a second time.” Fitzpatrick, perhaps slightly humbled, agreed that the drink had something to do with it.



The Making of a Legend

Thomas Fitzpatrick’s two late-night flights became the stuff of legend, especially in Washington Heights, where tales of his near-impossible landings circulated for decades. In time, his reputation was such that a drink called the “Late Night Flight” was named in his honour—an appropriate tribute to a man who could turn a casual night at the bar into an urban legend.

Yet Fitzpatrick’s life wasn’t defined solely by his airborne escapades. Born in Emerson, New Jersey, he’d lied about his age to join the Marines at 15, serving in China during World War II, where he learned to fly reconnaissance aircraft. After his time in the Marines, he joined the Army and became the first New Yorker wounded in the Korean War. Wounded while driving an ammunition truck to rescue trapped American soldiers, Fitzpatrick received the Purple Heart for his bravery.



He eventually settled into civilian life, working as a steamfitter with Local 638 in New York City and Long Island for over half a century. Fitzpatrick was also active in community groups, including the VFW Post #6192 and the China Marines Organization, living out his later years with the same fearless spirit that had fuelled his infamous flights.

Fitzpatrick under arrest

Legacy of the High-Flying Steamfitter

Today, stories of Thomas Fitzpatrick’s flights may seem almost too audacious to believe, but the facts speak for themselves. Fitzpatrick’s story captures a uniquely American spirit—a blend of courage, stubbornness, and a touch of recklessness. For the people of Washington Heights and aviation enthusiasts alike, his landings remain an astonishing slice of local lore, reminding us that sometimes truth really is stranger than fiction.


So, next time you’re in New York and hear about the “Late Night Flight” cocktail, raise a glass to Thomas Fitzpatrick—a man who truly took barroom bets to new heights.

 

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