A Small History of New York’s Biggest Ollies

Photo by Mike Heikkila. See how glorious non-Instagram resolution is? Didn’t even notice the guy peeking out of the bottom corner until seeing the full res on the Chocolate site.

Every day, we pull up to spots and begin rattling off their A.B.D. lists. The 2020 footage economy will even have you forgetting that Tiago switch back smithed the Columbus Park rail, and people in your Insta comments will yell at you about not including Sean’s back lip down Tekashi 10. (Didn’t have a digital copy of “BLESSED” on-hand, sheesh!)

Something that has only been ollied, however, is an entirely different topic. It is a conversation of how rather than what.

Skateboarding is accelerating faster than ever, but for a 2020 spot to have only one entry on its trick scroll is saying a lot about how large, sketchy and variable-dependent that feat is. Skate teams from all over the globe scour the city throughout its seven warm months, lead by tour guides who have pins to everything that could possibly be skated. It stands to reason that anything in the city that could be ollied, has been sized up by the most talented skaters on earth, summer after summer.

Take for instance the ollie from Carl Aikens’ “Welcome to Chocolate” ad. Can speak from personal experience that people have claimed this as far back as ~2005. It is across the street from one of midtown’s most-skated spots, next door to the nearest Duane Reade and Starbucks — it has no doubt been noticed by anyone exploring the neighborhood on a board. According to Carl’s Transworld interview, Matt Schleyer knew it, so it is likely that he’d shown it to people prior, only for them to pass on the opportunity. “Short run-up for a big ollie” is how he put it.

So we got to thinking: what other ollies stand as singular feats throughout the city? You can never say never with regard to tomorrow’s possibilities in skating’s collective progression, but you can be pretty confident that the first trick any of us ever learned will be the only trick on certain spots, for …at least a while.

The most obvious of these feats is T.J’s 33rd Street subway ollie. Here is something that every pack of skateboarders passed on their way up to midtown from Union Square for decades — Keenan Milton ollied the gold bar on its own in an old photo. It had been discussed by all of us, with Brandon Westgate often ending up being the head candidate for it, especially in those years when so much of his footage was filmed in New York.

But the logic went something like, “If Westgate hasn’t done it, maybe it’s not do-able.”

When T.J. finally pulled it off as the centerpiece of his 2018 S.O.T.Y. run, it had the skate-equivalent magnitude of a hometown team winning a championship. The best possible person to do this piece of maybe-one-day lore, did. The ollie earned three paragraphs in The New York Times, which described it “like doing a parabolic calculus problem with your body while also attempting suicide.”

Another longtime “maybe” conversation was embedded in the infrastructure of the city. The overall consensus was yeah, somebody could definitely ollie the distance between two subway platforms — but what station afforded the run-up without an impossible curve in, and who had the nerves to fly over an electrified third rail on a 24-hour train system? These were things we’d blabber about while waiting for a delayed train.

Koki Loaiza did it in Colin Read’s Tengu video at the 145th Street A station (heading towards the third rail, nonetheless), and it also ended up in The New York Times. (The controversy about how this may actually not have been the first subway ollie has been discussed on the pages of the website before.)

The reason Westgate became the de facto name people threw at the city’s largest hypothetical gaps was because he was doing shit like this throughout the 2010s:

This is not a spot. It is a waist high loading dock out of a curb cut, a bit of elevated cement that he had to maintain speed on, and then an ollie over a perpendicular set of stairs and a street. The approach is from a part of Canal Street that is paved bad, and he only throws his board down for it. It was in an X-Games “Real Street” edit, which doesn’t exactly have the longest staying power, but in those few years proceeding it, we’d all pass it on our way to Three Up Three Down, tell whichever visitor was with us the story, and proceed to wonder what the fuck he was thinking when he did this.

A lot of these spots are hidden in plain sight. This Jake Johnson ollie around the corner from Black Hubba has been passed by every single skater in New York. It is something of a spiritual continuation of Mike Maldonado’s iconic First Division ad, except it is off a ledge that’s barely the width of two boards, over a wall, onto a blindsided landing of the same size with a network of standpipes to the right, which are sure to mangle the human body — and it’s at the F.B.I’s New York headquarters. This ollie is maybe the most insane thing Jake has done that was not in a proper part of his.

On that same token, every weekend, anyone skating midtown makes an inevitable pitstop at Brick Nine. Hardly anybody notices this “gap,” to the right of it, because it’s …again, not a gap. It has little runway, is head-high off the street, over a spiked fence, and with an even shorter landing, e.g. if someone got pitched going forward, there’s about six feet of stone before you fly down onto street level.

Photo by Zach Malfa-Kowalski

Sometimes, while everyone is in line to huck, someone extra nerdy will remember, “Didn’t some Australian ollie that?” Only to be followed up with, “Ollie what?” while looking over for the gap (notice how hard it is for a video angle to do it justice.) The fact that it was in an international montage of an old Habitat video didn’t do it many favors. (It’s by Bryce Golder, btw.)

And now we arrive at one of the most well-known parables of New York skateboarding: If you’re wondering if somebody has ollied something big before, the answer is probably, “Yes, some guy on Natural Koncept did it.”

Brooklyn’s Tompkins Park has a mini Leap of Faith gap from park level down to the bowels of its amphitheater. Boner did it in a Natty Kon tour video, and it is always wise to remind the inevitable inquisitive gentleman sessioning the lower impact portions of the spot that, “Yes, some guy on Natural Koncept did it.”

Out of all the places on the downtown spot loop that you could get stuck at, Family Court has a particular brand of tedium. Something about a high manual pad really tests group morale unlike anything else. Which is why we often find ourselves in conversation about this particular gap. Sage jumped it and it was a clip in “cherry.”

Has it been ollied? “Yes, some guy on Natural Koncept did it.”

But last time we got stuck in this grey purgatory, a heated debate came up: if the gap below was a fall to your death, and you either had to ollie or jump it, with the understanding that you had to stick the ollie to live, which would you rather do?

The two people present who are paid to skate insisted that you have better chances at continued life with an ollie. Considering that one guy tried to Sage the 145th subway tracks and failed, you get a feeling that maybe they’re right.

You running and jumping or ollieing to your death?

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Previously: A Short History of New York’s Longest Lines


  1. If I died running and jumping, then video evidence would be relegated to some morbid website for creeps. If I die trying to ollie it, I’d be enshrined in local skate lore AS WELL as morbid websites. This is, categorically, a firmer legacy.

  2. Jeremy Wray said jumping the tower gap was scarier than ollieing it. I’ll take his word for it.

  3. Someone ollied the police plaza 16 I think it was a black and white photo possibly a melon grab tho

  4. Someone needs to ollie D7 sideways getting run up from north direction then over the west set of blocks into the square. I sized it up someone’s got that. Also ollie over D7 rail kinda fucked

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