We’ve all done some stupid shit when drinking; dancing, fights, arguments, hook-ups, whatever can be done, humanity has done it many, many times over. But there are very, very few people who can claim to have drunkenly committed grand theft airplane and lived to tell the tale… not just once, but twice! This week, we’ll take at one of the biggest badasses in the history of New York.

Thomas “Tommy Fitz” Fitzpatrick

Born: 1930, Washington Heights, New York City

Died: 2009, Washington Township, New Jersey

Occupation: USMC, steamfitter, pilot extraordinaire

Tommy Fitz was a New York boy through and through: born in Washington Heights in the north of Manhattan, he spent almost his entire life in the city and surrounding area, save for his stint as a Marine in the Korean War, where he was wounded and received a Purple Heart for his service. After returning home, he worked as a steamfitter, was married to his wife Helen for 51 years, and had three sons with her. All the same, he had ample time to get into a lot of trouble.

On September 30th, 1956, 26-year-old Fitzpatrick was out drinking at a bar in Washington Heights when he made a bet with a friend that he could make it back from New Jersey to Manhattan in 15 minutes or less; in the dead of night, he slipped off to the Teterboro School of Aeronautics (about three miles north of where MetLife Stadium is now) and stole a single-engine plane. At 3 o’clock in the morning, and absolutely plastered, Fitzpatrick took off, with zero radio or instrumental assistance, and made the short flight back to the bar, landing the plane safely on St. Nicholas Avenue just south of 191st Street. A few incredible things about this, besides the fact that Fitzpatrick was shittered drunk when he flew the thing:

• St. Nicholas Avenue is not a particularly wide road, and the fact that cars were parked on both sides of the street as well as the lampposts dotting the sidewalk made his landing even tighter.
• He’d initially intended to land on the playing field next to George Washington High School, just to the northeast of St. Nicholas Avenue, but with no lights on the field, it was almost impossible to tell where the field began and ended, thus leaving St. Nicholas Avenue as the only possible option for a landing.

Fitzpatrick was initially charged with grand larceny, but when the plane’s owner refused to file a complaint, he received only a $100 fine for his flight, for breaking the city ordinance that forbids landing a plane on a city street. He also had his pilot’s license suspended for six months, but never bothered to renew it after that incident anyhow.

A little over two years later, Fitzpatrick did it again.

Why?

His drinking buddy didn’t believe it that he’d actually made the first flight. To prove him wrong, Fitzpatrick got hammered, stole a second plane, taking off just before 1 AM on October 4th, 1958, and made another miraculous landing on Amsterdam Avenue at 187th Street, just a few blocks  away from his first flight.

This time, however, Fitzpatrick was not so lucky afterwards with the law; he spent six months in jail for this flight, found guilty of bringing a stolen item into the city; at his sentencing for the crime, the judge remarked “Had you been properly jolted then, it’s possible this would not have occurred a second time.” Regardless, Fitzpatrick never broke the law again, and lived to the age of 79. Lesser men would never have been able to pull off such a crazy feat as this; completing it successfully twice makes it clear that Tommy Fitz is without question a true historical badass of the highest calibre.