On 21 April 2019, the Facebook page “Pictures in History” posted an image of a small plane in the middle of a New York Street and a brief paragraph explaining the photograph’s alleged backstory, which involved a man named Thomas Fitzpatrick, a drunken bet, and some impressive aerial maneuvers:

The Facebook post reads: “On September 30th, 1956, during a drunken argument in a New York City Bar, a man named Thomas Fitzpatrick claimed he could fly an airplane from New Jersey to New York in under 15 minutes. To prove himself, Fitzpatrick left the bar, stole an airplane from a New Jersey airfield at 3am, flew without lights or radio completely intoxicated, and landed the airplane in the street in front of the bar. The owner of the plane was so impressed that he refused to press charges, and Fitzpatrick was only fined $1000 for his stunt. Two years later, Fitzpatrick got into another drunken argument in which another bar patron refused to believe his wild story, so he did it again. This time finding himself in prison for 6 months….The Original ‘Hold my beer story.’”

While the “Pictures in History” Facebook page has shared a number of fake or miscaptioned images, this story is largely accurate.

We found several contemporary reports that support the story published by Pictures in History. However, some of the smaller details, such as the nature of the original bet, are still a bit unclear:

Mon, Oct 1, 1956 – Page 1 · Democrat and Chronicle (Rochester, New York) · Newspapers.com

The New York Daily News reported on 1 October 1956 that Thomas Fitzpatrick, 26, was drinking at a Washington Heights ginmill after a bachelor party when he suddenly got the urge to fly. Fitzpatrick drove to the Teterboro Airport in New Jersey where he “borrowed” a Cessa 140 two-seater plane — he apparently knew one of the owners — and then flew it back to Manhattan, where he landed on a narrow street.

Fitzpatrick originally explained his actions by telling police that he was forced to land on the street due to engine trouble. Police were skeptical of this story, however, and suspected that this late-night, booze-inspired flight may have actually started with a bet. After all, Fitzpatrick’s journey started and ended near the same ginmill:

After inspecting the plane police said the odds also were very heavy against his explanation. They found no evidence of any engine trouble. As a matter of fact, they said, considering that the same ginmill figured in both takeoff and landing, they suspected the stunt was the result of a bet.

Fitzpatrick also claimed that he had “borrowed” the plane. Whether this part of the story is true is a bit irrelevant at this point, as the owners of the plane didn’t press charges. Fitzpatrick only received a $100 fine for the stunt.

Jim Clarke, who lived in the neighborhood at the time, told The New York Times in 2013:

“The story goes, he had made a bet with someone in the bar that he could be back in the Heights from New Jersey in 15 minutes,” said Jim Clarke, 68, who had lived near the first landing spot and recalls seeing the plane in the street. “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,” said Mr. Clarke, who now lives in Chatham, N.J. After the first flight, Mr. Fitzpatrick was arraigned on grand larceny charges, which were dropped after the plane’s owner declined to sign a complaint. He was also charged with violating the city’s administrative code, which prohibits landing a plane on the street. Mr. Fitzpatrick was only fined $100.

Fitzpatrick’s story is certainly a bit unbelievable. So much so that one bar patron was skeptical of the tale when Fitzpatrick recounted his adventure a few years later. In order to prove to his drinking buddy that he was telling the truth, Fitzpatrick once again drove to the Teterboro Airport to “borrow” a plane and then flew it back to the bar.

The Daily News reported at the time:

Fitzpatrick said he was in a bar in Manhattan Friday night with the Nutmegger (a person from Connecticut) and he began talking about his 1956 escapade. The other man was skeptical. Things were settled by a trip to Teterboro Airport in new Jersey, the Connecticut man driving. Fitzpatrick picked out the same kind of plane, owned by the Teterboro School of Aeronautics, and with no by-your-leave to the control tower, roared off from west taxiway, oblivious to the possibilities of hitting other planes. A few minutes later Fitzpatrick, who admits he considers himself “one hell of a pilot,’ shot his Amsterdam Ave. landing, scaring at least one motorist and one bus driver. The motorist, John Johnson, 34, a carpenter, of 811 Kelly St., Bronx, had to jam on his brakes to avoid being hit.

Fitzpatrick’s second impromptu plane ride landed him six months in jail.