The Pilot Who Stole Planes Twice to Win Bar Arguments

Some people talk a big game at the bar. Thomas Fitzpatrick actually followed through—twice. In the early morning hours of September 30, 1956, the WWII veteran was drinking at a New York City bar when he got into an argument about whether he could fly a plane from New Jersey to Manhattan in under 15 minutes. Most people would have let it go. Fitzpatrick walked out, headed to the Teterboro School of Aeronautics in New Jersey, and stole a single-engine Cessna 140.

At 3 a.m., completely intoxicated, he flew without lights or radio across the Hudson River and landed the plane on St. Nicholas Avenue in northern Manhattan—right in front of the bar where he'd been drinking. The narrow street landing was considered an impressive feat of piloting, even if it was completely illegal.

The Consequences Were Surprisingly Light

Fitzpatrick was arrested and charged with grand larceny and violating city codes that prohibited landing aircraft on streets. But here's the twist: the plane's owner declined to press charges. The larceny charge was dropped, and Fitzpatrick walked away with just a $100 fine. Most people would have learned their lesson.

Thomas Fitzpatrick was not most people.

Two Years Later, He Did It Again

On October 5, 1958, Fitzpatrick was at another bar when he encountered a patron from Connecticut who refused to believe he'd actually pulled off the 1956 stunt. Rather than show the man a newspaper clipping or court documents, Fitzpatrick decided on a more direct approach: he'd simply do it again.

Once again, he stole a plane from New Jersey—this time a red-and-cream Cessna 120—and landed it on a Manhattan street, specifically Amsterdam Avenue near 187th Street. This second landing proved his point beyond any doubt, but it also proved he hadn't learned anything from his first arrest.

The Second Time Wasn't the Charm

The judge was less amused the second time around. Fitzpatrick was sentenced to six months in jail. Even so, the punishment seems remarkably light for someone who twice stole aircraft while intoxicated and landed them on city streets filled with pedestrians and buildings.

Thomas Fitzpatrick's double feat has become legendary in aviation circles, often cited as one of history's greatest "hold my beer" moments. He died in 2009 at age 79, having lived long enough to see his youthful stunts transform from criminal acts into the stuff of bar-room legend—the very environment where they began.

The story raises an obvious question: how did a drunk man successfully navigate and land a plane on a narrow city street not once, but twice? Fitzpatrick was a WWII veteran and experienced pilot, which explains the technical skill. The sheer audacity and questionable judgment? That part remains harder to explain, even decades later.