Drunken Night Flights

The Night Thomas Fitzpatrick Landed a Plane on a Manhattan Street: A Tale of Aviation, Alcohol, and Audacity

In the annals of aviation history, few tales are as wildly audacious and humorously bizarre as that of Thomas Fitzpatrick, a man who, fueled by alcohol and a hefty dose of bravado, managed to land a plane on a Manhattan street. Not once, but twice. This is the story of how a late-night bar bet turned into one of the most legendary feats of daredevilry in New York City’s history.

The Man Behind the Legend

Thomas Fitzpatrick, often known as “Tommy Fitz,” was not your average pilot. Born in 1930, Fitzpatrick was a seasoned aviator with a penchant for thrill-seeking. He had served as a Marine during the Korean War, where he undoubtedly honed his flying skills. After the war, he returned to civilian life, but his love for flying and adventure never left him.

The First Flight: September 30, 1956

The scene was set on a cool September night in 1956. Fitzpatrick found himself at a bar in Washington Heights, New York City, enjoying a drink or two… or three. As the evening progressed, a spirited (no pun intended) debate erupted about the difficulty of flying from New Jersey to New York and landing in Manhattan. Fitzpatrick, always up for a challenge, boasted that he could make the trip in just 15 minutes. His friends, perhaps sensing an opportunity for entertainment or simply doubting his claim, bet against him.

Betting against someone who lied about his age in order to serve in World War II, at the age of 15, turned out to be the wrong bet to make.

Without much ado, Fitzpatrick slipped out of the bar and headed to Teterboro Airport in New Jersey. With the great courage he had built up over World War II the alcohol he had consumed, he “borrowed” a single-engine plane – a Cessna 140 – under the cover of darkness. Fitzpatrick, displaying an extraordinary level of inebriated audacity and skill, navigated the plane through the complex urban landscape and made a flawless landing on St. Nicholas Avenue, right in front of the bar where the bet had been made.

image credit check-six.com

The Reaction

the plane in the city
Plane getting ready to be carried away by authorities, with the wings removed.

The patrons were understandably stunned. Here was their friend, standing triumphantly next to a plane parked in the middle of a New York City street. Fitzpatrick’s late-night aviation stunt earned him a hero’s welcome in the bar and a less enthusiastic reception from the authorities.

Fitzpatrick’s arrest by the police.
Image credit check-six.com

Despite the inherent danger and illegality of his actions, Fitzpatrick was initially fined a mere $100 for his daredevil landing. The judge, perhaps a little impressed by Fitzpatrick’s audacity, or possibly bemused by the absurdity of the situation, went relatively easy on him.

Credit: The Herald News, 1957

The Second Flight: October 4, 1958

One would think that such a stunt would be a once-in-a-lifetime event, but not for Thomas Fitzpatrick. Almost exactly two years later, on October 4, 1958, Fitzpatrick found himself once again in a bar, recounting the legendary story of his midnight landing. His audience, perhaps skeptical of his tale, challenged him to repeat the feat. And repeat it he did.

This time, Fitzpatrick took off from an airstrip in New Jersey, and once again, he piloted a plane through the night sky, navigating the urban jungle with a precision that defied his inebriated state. He landed on Amsterdam Avenue near 187th Street, only a few blocks away from his first landing site.

Credit: Eugene Register Newspaper, October 5th, 1958 edition

The Consequences

While his friends and fellow bar-goers might have been thrilled by his encore performance, the authorities were less amused. Fitzpatrick’s second stunt earned him a six-month jail sentence. The judge, who likely saw Fitzpatrick’s repeated antics as a step too far, decided that a stronger message needed to be sent this time.

The Legacy

Thomas Fitzpatrick’s late-night flights have gone down in history as some of the most outrageous and daring stunts ever performed in the heart of New York City. His actions were undoubtedly reckless, but they also showcased a level of skill and nerve that few could match. Fitzpatrick’s story is often retold with a mix of admiration and disbelief, a testament to his unique place in aviation folklore.

Humor in Hindsight

Looking back, it’s hard not to find humor in the sheer absurdity of Fitzpatrick’s actions. The image of a plane landing in the middle of a bustling New York street is the stuff of movies and urban legends. The fact that it happened not once, but twice, because of barroom bravado and a pilot’s unwavering confidence, adds a layer of comedic incredulity to the story.

Imagine the reactions of the people on the street: one moment, they’re going about their late-night routines, and the next, a plane descends from the heavens, piloted by a grinning, slightly tipsy aviator. It’s the kind of scene that defies belief and prompts a double-take, even decades later.

The Man and the Myth

Thomas Fitzpatrick lived the rest of his life as a working man, and though he never pulled off another aerial stunt quite like those infamous landings, his legend lived on. He passed away in 2009, but his story continues to be a favorite among aviation enthusiasts and those who appreciate a good, old-fashioned tale of daring and recklessness.

In a city known for its larger-than-life characters and unbelievable stories, Thomas Fitzpatrick stands out as a true original. His late-night flights are a reminder that sometimes, the most extraordinary feats come from the most unexpected places – and that a little bit of bravado can go a long way, especially when you have the skills to back it up.

So next time you find yourself in a bar, boasting about your abilities, remember the story of Thomas Fitzpatrick. And maybe think twice before accepting a dare that involves borrowing an airplane. Or don’t. After all, legends aren’t made by playing it safe.

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