In the crowded catalog of New York City oddities, Thomas Edward “Tommy” Fitzpatrick still stands out. Twice in the 1950s, after nights of drinking in Washington Heights, he “borrowed” small planes from Teterboro Airport in New Jersey and landed them on Manhattan streets a few blocks from the bars where the boasts began. The landings were illegal, dangerous, and — by contemporary police and newspaper accounts — astonishingly precise.
Core facts below follow Wikipedia’s summary, the New York Times City Room retelling (2013), and the detailed chronology at Check-Six.
Who was Tommy Fitz?
Fitzpatrick was born April 24, 1930, and died of cancer on September 14, 2009, at age 79. By the mid-1950s he lived in Emerson, New Jersey, and worked as a steamfitter. He also took flight lessons at the Teterboro School of Aeronautics — which matters, because both street landings started from that field.
Military biography needs a careful voice. Family accounts (including his brother’s, as summarized on Wikipedia) say he lied about his age to join the U.S. Marine Corps around age 15 near the end of World War II and later served in the U.S. Army during the Korean War, where secondary sources say he was wounded and received a Purple Heart. That is not the same as “Marine during the Korean War,” which earlier versions of this story sometimes blurred. Treat wartime details as reported family/secondary history, and treat the two Manhattan landings — which newspapers covered in real time — as the solid core of the legend.
Flight 1: September 30, 1956
On the evening of September 29 into the early morning of September 30, 1956, the then-26-year-old Fitzpatrick was drinking in Washington Heights (Check-Six places the scene at a corner bar on 191st Street called Joe’s). Someone bet he could get from New Jersey to New York City in 15 minutes. He left, went to Teterboro, and took a single-engine Cessna 140 from the Teterboro School of Aeronautics flight line — without lights or radio contact, according to later reporting.
Around 3 a.m., he landed on St. Nicholas Avenue near 191st Street, between parked cars and apartment buildings, close enough to the bar that the stunt finished the argument in the most literal way possible. Contemporary coverage and later NYT interviews called it a near-impossible “feat of aeronautics.” One often-repeated detail: he may have aimed for the dark field at George Washington High School and diverted to the lit street instead.
Police and Civil Aeronautics officials were not amused. He was arraigned on grand larceny and a city administrative-code charge for landing an airplane on a street. The plane’s owner declined to press the theft complaint, so the felony dropped. Fitzpatrick was fined $100 for the street-landing / aviation violations; Check-Six also reports a six-month pilot-license suspension. For a first offense that could have killed bystanders, that was a remarkably light landing of its own.
Image credit check-six.com
Flight 2: October 4, 1958
Almost exactly two years later — October 4, 1958, just before 1 a.m. — Fitzpatrick was again drinking in Washington Heights and telling the 1956 story. A patron refused to believe him. Cue round two: back to Teterboro, another unauthorized takeoff, this time in a Cessna 120.
He landed on Amsterdam Avenue at 187th Street, in front of a Yeshiva University building — only a short walk from the first touchdown. Witnesses described a gray-suited man hopping out and running. Police matched fingerprints and called him in; the second act was harder to shrug off as a one-night miracle.
In January 1959, Judge John A. Mullen sentenced him to six months in jail. Contemporary quotes capture the court’s mood: the first fine had not been enough of a jolt, and New York streets were not going to become an airstrip. Fitzpatrick blamed “the lousy drink.” After prison, as far as reliable accounts go, he did not try for a third curtain call.
Flight 1 vs Flight 2 (quick facts)
| Detail | Flight 1 | Flight 2 |
|---|---|---|
| Date / time | Sept 30, 1956, ~3 a.m. | Oct 4, 1958, ~1 a.m. |
| Aircraft | Cessna 140 | Cessna 120 |
| Departure | Teterboro School of Aeronautics, NJ | Same field / area |
| Landing | St. Nicholas Ave near 191st St | Amsterdam Ave & 187th St (near Yeshiva University) |
| Trigger | Barroom 15-minute bet | Patron disbelieved Flight 1 story |
| Main penalty | $100 fine (theft charge dropped) | 6 months in jail |
Why the story still lands
Strip away the barroom bravado and you still have two night landings into a canyon of brick, lampposts, and parked cars — performed drunk, without clearance, in light training planes with roughly 32-foot wingspans on ~60-foot-wide avenues. Skill does not make the stunts wise. It does explain why police aviators called the first touchdown almost impossible, and why the tale keeps getting retold.
Fitzpatrick spent most of his life as a working steamfitter and community member in New Jersey, not as a perpetual skyline daredevil. The drink named in his honor in some retellings — the “Late Night Flight” — is folklore garnish. The documented core is simpler: two dates, two streets, two planes, a $100 fine, then six months behind bars.
So if someone in a bar insists they can “get there in 15 minutes,” smile, buy the next round, and leave the Cessnas where they belong.
Further reading
Logitech G Pro Flight Yoke System
A desk-clamp yoke and throttle quadrant for Microsoft Flight Simulator and X-Plane, the legal way to practice a Manhattan approach from your own chair.
Thrustmaster T-Flight Hotas X
A stick-and-throttle HOTAS for PC flight sims — pair it with a yoke or use it alone when the night-flight practice session turns into dogfight practice.
Logitech G Pro Flight Rudder Pedals
Floor pedals for yaw and brakes in Flight Simulator — the missing feet for a yoke setup when you are lining up that drunken night approach.