Andy Kessler x Vans Syndicate Sk8 Hi Reissue NYC 'S'

Vans has finally given us details about the Andy Kessler Syndicate reissue of his iconic Sk8 Hi. Changes to this model include updated materials and a higher foxing. We get a really nice mix of premium leather and nubuck on the upper and the all blacked out Off the Wall tongue tag is a great detail. 

This sneaker is really more than just a sneaker. It's an homage to Kessler. And I would really like that to be the focus of this article. Tony Farmer did a beautiful write up for Vans about Andy Kessler's legacy. I know a lot of you are too young to remember who he was or witness the impact he had on skate culture, so if you have the time, I urge you to read Tony's words. 


Nothing beats an untimely death in securing one Legend status. Suddenly you’re larger than you ever were in real life, everyone is your tight bro from way back when, and no one speaks a negative word. Was Kess truly a legend? The godfather of skateboarding in New York City? Maybe, maybe not. Reality most likely lies somewhere in the margins. Doesn’t really matter. What matters is what he did and how he did it. These are the things I can speak to. 

Kessler paid his dues. He cheated death on more than a few occasions. Coming out the other end, he made it a mission to give back. Or, when necessary, to take back. He guided many a soul through the trials of recovery from substance abuse. He raised hell at board meetings and got skate parks built in a city devoid of them. He mentored kids, and busted people’s balls. He was beloved, and despised. He knew EVERYONE. He was my friend, and miss him every damn day.

I don’t pretend to know his whole story. I’d like to think that no one does. He ran in a lot of different circles, overlapping and intersecting and binding otherwise dissimilar people together in the process. He was a skater, foremost. What else? A junkie, miscreant, hell raiser, pool shark, Zappa fan, shit talker, sponsor, goon in Guatemalan pants, surfer, brother, adopted son, angry Greek bastard, perv, sticker collector, Thrasher cover star and kite flying enthusiast.

I don’t know all his stories. But I’ve got a personal cache that I cherish, moments that come and go in my head as I wander the streets of this great city.

If there be an underlying theme to Kess’ tale, it would be one of perseverance. The myriad stories that I am privy to, from the minor ones I experienced firsthand to the ever-growing legends spun by word of mouth, are all sewn together by the common threads of survival and dedication. From minor political victories to life changing influences, his stories run the gamut. 

Kess spent countless hours in board meetings fighting to get skate parks built in New York City. I’ve been to a couple of these, and they are brutal. Both mind numbingly boring and exasperatingly frustrating given the layer upon layer of red tape and bureaucratic bullshit. I can’t stomach them, but Kess would never let up. He bashed his thick skull against the wall of the Parks Department for years on end, and he got shit done. They might not be the best parks in the country, but they were progress, and the momentum he helped to create has delivered us unto spots like Chelsea Piers. It’s a damn shame he never got to ride a proper skate park in his City after all the years he spent suffering without.

The fact that he was skating at all is amazing. It wasn’t that long ago that the idea of 50 year old men still skating on a high level seemed absurd. Of course, it’s become quite common: see Tony Alva, Steve Alba, Lance Mountain, etc. Still, when your over forty and suffer a severe leg injury like a broken hip, it’s understandable if one decides he’s had enough and hangs it up. Sure, maybe he still jumps on a cruiser board to run down to the store, but only a true blue skater is coming back from that and pushing himself in the bowl as if it never happened within a year’s time. I am not going to lie, those first few sessions with Kess afterwards were worrisome. But he was as hell bent as ever, calling the crew, rallying the sesh, and I’m claiming dude cracked the best frontside air of his life post-op at Autumn. Ask Olson, he’ll tell you the same. I’ll steal a line from their pal Jocko Weyland: when was Kess gonna grow up and quit skating? The Answer was Never.

As skaters, we are often blind to the fact that the real world exists around us. We see everything through the lens of a skater, sometimes oblivious to other concerns. While Kess’ contributions to the skate scene in New York cannot be understated, it must be heralded that he managed to do a lot more important and impressive work elsewhere in the community. Andy was a recovering addict. I never knew the Kess of old; the junkie thief fuck-up. This town is littered with stories of those that kept on spinning right down the drain. Andy had every opportunity to keep using and wind up in the joint or, more likely, wake up in the gutter dead. But he didn’t. He got himself sorted out and sobered up. He was ever “clean,” he always bristled at that term. He was still a dirty old bastard, but he was sober the entire time I knew him. As impressive as that is (especially given the 24 hours of opportunity to blow it that this town presents), the real story is what he did for others. A big part of the Program is sponsorship; those who are sober lending a helping hand to others who are new to recovery, as well as those who have fallen off and are coming back. Andy always had someone he was looking out for, getting them to meetings and being a friend. I don’t pretend to know how many he helped, how many stayed true or how many he lost. But I do know that he literally died trying, with a dear friend and repeat junkie sleeping in his bed as he passed away.

Let’s not end it there. Like I said, his legacy is one of keep on keeping on, of not giving in, nor giving up. I’ll share one of my personal favorites about my guy. Kess died on the east end of Long Island, in Montauk. He’d been focusing on learning how to surf during the last few years of his life. Surfing is not easy, trust me. Skaters often make the mistake of thinking that the skills translate, that they’ll be ripping in no time at all. That’s what I thought. I was wrong. Like most anything worthwhile, it takes thousands of hours of practice to master. It is also something best learned at a young age (as I did). I give a lot of respect to people who pick it up as adults and manage a degree of competence. Kess was driven to feel as free and comfortable in the water as he did on his skate. He picked my brain about surfing’s nuances, all the little pieces that put you in the right place at the right time, like being tucked in the barrel with your buddy paddling over shoulder throwing you a shaka. (That sounds utterly ridiculous, but it’s true.) Anyway, the weekend before Kess passed there were waves. The two of us hiked down the beach to escape the crowds. The moment he started paddling out I knew he was fucked, that the current was going suck him into the rocks and he was gonna get drilled. I adjusted my entry point, and made the line up fairly easily. Meanwhile, Kess was getting his head beat in as set after set rolled over him. Each short lull he’d make some progress, only to be denied by another set wave. I couldn’t help but laugh as he screamed with frustration. After a long beat down I could see him back on the beach. The poor bastard had given up, and now had to sit and watch. But next thing I knew Andy Kessler came paddling up to me with a big “FUCK YOU, FARMER!” He told me there was no way that he was gonna sit there a watch me surf my brains out without him. I was so happy for him, proud even. He had every reason to give up; the waves were borderline beyond his ability, he had the wrong board and he was old and tired. But he made it out and scored some great waves. He might still be a barney in many eyes, but as far as I was concerned, he was a surfer at last.

I fancy myself a New Yorker nowadays, and part of that claim comes by way of Andy Kessler. He was the first true New Yorker to embrace me, take me under his wing and show me the City in different lights. From swerving down the avenues through rush hour traffic, to quiet bites at Sidewalk talking story, the New York that I know and love was shaped through Kess’ eyes. Thanks for the aloha, pal. I hope I see you on the other side.

The Andy Kessler x Vans Syndicate Sk8 Hi Reissue NYC 'S' is scheduled to release at Vans Syndicate retailers this month and may already be on the shelves at your local dealer.

Shred in peace, Andy. 

Shred in peace, Andy.