I convinced him that they fit, I remember showing up at a kid party and instantly everyone noticed that my shoes were too big for my feet. But… they were the really sick Hawaiian print Vans from way back, that must have been 1983.

Since the beginning it was Vans, then the red checkerboard high-tops. I did the custom order that they used to have in the back of magazines. It said 8-12 weeks, and it took months and months and months… waiting for the UPS dude to come. I did a pretty wild pair, checkerboard on the outside, Hawaiian on the inside, red tongue on one, blue tongue on the other, they were nuts but they were so cool.

All the stuff you are mentioning is all stuff that Vans has brought back, that skaters wear now… the Hawaiian print and custom orders. But for a long time those shoes were hard to get. Did you ever have the lace-savers?
That’s embarrassing dude, not only the lace-saver that came with the shoes but i’d lace in an extra one to the front of the checkerboard Vans.

Its funny we are talking about it, because I just went to NY for that bike show there, and was having a full shoe crisis, cause I wanted to skate a bit, but I wanted my shoes to look right. And none of the shoes I had were right so went to the local college kid store and bought some navy Vans boat shoes (Authentics)… the navy blue and white ones, cause those always look so good. I shoe-goo’d the ollie area, cause I knew I was going to skate in Brooklyn…. and still I look down and remember the smell of the first box.

Any other weird shoe trends?
Cutting down full-cabs to half-cabs was pretty big in my day. Rick Howard was the first one I saw do that, and I was like ‘that dude is a fucking genius, that looks sick.’ I always thought the Half-cab could have been Rick Howard’s pro-shoe as well.

You ended up skating for Vans?
I did, off and on. Being a vert skater, you are already back against the wall, we travel with knee pads, and if you have some lame ass shoe on, its even worse, pointing out the herpes sore. In that first Real video I even said “I’m working on being marketable,” cause they had told me “we want you to ride for Real, and we want you to go far, but the reason James Kelch’s board sells is cause he looks cool and he’s a figure at EMB, and on top of everything he’s marketable” And I remember leaving the office and thinking ‘that fucking sucked, that conversation was fucked up,’ and basically they were saying, ‘don’t be a vert goon.’

Were there things you needed different for your shoes as a vert skater than a street skater?
You know what, I didn’t think so, I remember thinking whatever shoes my peers were wearing, like Mike Carroll’s Chukka Boots look sick. I think its all the same, I still skate in Era’s or Classics. I still wear low tops on vert. But because I was around Jake Phelps, who was wearing bigger shoes, I thought you needed hi-tops on vert, but then I realized, it didn’t matter, you were going to get fucked up either way. And I just want to feel my board most of all. I have been skating in Vans Era’s, I had 40 pairs that Vans sent me… but I ran out the other day and was skating some poka-dot Dollins. They were a pro series with a removable insole, which I hadn’t had in awhile, and I skated in them and it was one of the best sessions of my life. I’m sure it didn’t have just to do with the shoes, but I could still feel the board. So, I might be skating those for awhile.

What about the shoe for Syndicate? Did you have a lot of things you wanted to incorporate?
Yeah, without a doubt. I was working with that dude Jon, who is a designer. I don’t know if he’s still there, he writes for Hypebeast as well. And he came to the house with a sketchbook, and we sat there and sketched this shoe out… I’m sure you don’t know this, but I’ve been skating everyday lately, and I’ve been filming… but 10 years ago, I was so wrapped up in the motorcycle thing, and it was at the beginning of it becoming fashionable, and I remember asking “is this for skating or bike stuff?” and they said “it doesn’t have to be skating, if you want to make it functional for your motorcycle then do that.” So that is where I went with that. At the time I hadn’t seen the Mountain design in forever, and I said ‘that Mountain shoe is rad for your bike, cause right where your shifter goes, there’s that little lace saver.’ And I wanted the inside tire, its like an asymmetrical shoe, the inside is a higher high-top then the outside, I was like ‘the motor gets hot and it will protect your ankles.’ We tried to get that silver flame proof material, but it was too expensive. It has that little brass bolt on it, cause all my 4Q bikes have that brass hardware. There was a shit load of input actually on the high top of that shoe.

And this year we are doing an all black version, which is something I wanted originally, but it didn’t make sense at the time because it didn’t work with the red and white ones as a set. Its kind of cool that its going to be all black, because I still have an all black sample at the time Jon was like “this all black one is so rad, but then it would mean the red one would have to be all red and that would be too loud.” I wanted the red and white one because of Oakland and the H.A. and I thought it would be cool.

And you changed the logo from the mountain to the bridge?
Well, a lot of people think its the bridge, but its actually the crane, one of those Oakland ship yard cranes.

And the insole is a gas tank?
That’s right, it has fish scale on the inside? I was way into painting those at the time.

And the box looked like a box for motorcycle parts?
Yeah, I actually gave them a box for an old Harley part that had mildew on it. It actually had a spark plug in it from the 60’s… and I remember getting the sample with the box and just thought it was out of sight, I remember being so stoked on just the box. Some people even thought there was really mildew on the box. I have twenty here and when they are stacked it looks sick. Part of the deal was when we did the shoe, I got quite a bit of them to give to my friends and skate them over time, and they look pretty neat stacked up.

Its cool you got to have that much input in the shoe. Sometimes its just a color-way and thats it.
Well, as I was saying, I’m kind of a vert skater, and not marketable, so when they came to me it was shocking that I spent so many nights thinking about it, and when they finally came to me, I had all these ideas. And I think that surprised them. I was getting some recognition in Japanese bike magazines, and I think they just were like “let’s pour everything into this one and let this geek go off with it.” It had a killer box, and cool bag, and motorcycle grips. It was high-top, low-top and two colors. And at the time they told me it sold better than any other Syndicate shoe, and I think so much of it had to do with that they put the extra buck into it. They did say they weren’t going to make a dollar on it, but it was a cool project. I was really shocked how much they agreed to do.

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.

This year marks the 10th year anniversary of Syndicate.  We are bringing back some of favorite shoes and collaborations.  Is the anniversary model a color you wanted to make before?  What was the process behind the updated version?
It's actually a color I never really imagined, but when the guys approached me with the idea I thought it was fresh.  The updated version was mostly put together by the Syndicate guys.  I had some input, but it's really been their initiative. 

Was designing the Vans Syndicate shoe a new experience for you at the time?  Tell me a little bit about your background at Supreme as well as school and how that informed this shoe.
It was a new experience because while I'd worked with Vans (through Supreme) for a long time, this was the first shoe that was a completely new style that I was able to make.  I started designing for Supreme in 1999, and working with James (Jebbia) and all the talented people there definitely helped to shape my approach to making things.

You designed the shoe from scratch or based on an existing model?
The upper of the shoe was designed from scratch, but we used a classic Vans vulc outsole.

Most of the time when people do shoes for Vans they are color-ways or slightly altered versions of their classics.  Do you like the classics?  Did you ever wear any of them growing up?
I grew up with Vans, and have had most of their classic models at one time or another.  I got my first pair when I was about 8 or 9 years old.  Freshest kid in school that day ... black and white checkerboard slip ons.  I have always had at least one pair of Eras or Authentics ever since.

What were the styles that inspired the shoe you designed?  Did you want something skateable or more fashionable.
Because the idea was 'Destroy Luxury', I wanted to make a skate shoe of luxurious materials that was supposed to be shredded.  Even more, I wanted people who skate to really like the shoe for skating; style is the bonus.  Many different people have told me that they like to skate in the shoe, so I think it was successful in that regard.  There wasn't a particular style that inspired the shoe, it was more an approach of how can I make a shoe with Vans DNA look a bit more 'luxurious'.

Is the piece on the side for ollie protection?
Yeah.  It's the spot on a skate shoe that gets the most abuse, so I put the most luxurious material there ... to be destroyed.

Was it cool to imagine people skating in the shoes?
It's the main reason I wanted to make them.  Vans and skateboarding can't really be separated in my mind.  Skateboarding has had such a profound effect on me, and Vans is part of that.  For that reason I will always revere the brand.

Harmony was one of the people in my life who introduced me to art. Whether taking us to see a Woody Allen movie like Shadows and Fog (1991), or a screening of My Own Private Idaho (1991), or going to watch KRS-1 speak at Vanderbilt University, he helped open my eyes to a different way of thinking and looking at the world. I was a young, impressionable mind soaking up everything around me. At that time, I was completely enthralled with skateboarding and those who loved it, which hasn’t changed to this day.