Steve Caballero: Skateboard Legend and Motorcycle-Riding Badass

Bones Brigade skater discusses love for two wheels, slinging old skateboards online to build vintage bikes and meeting Evel Knievel

Steve Caballero with some of his vintage skateboard decks. Credit: Eric Hendrikx

"I've  had a long-standing relationship with motorcycles, from growing up in the seventies and looking up to Evel Knievel," says Steve Caballero, seated next to his Evel Knievel signature pinball machine at home in Carlsbad, California. An early pioneer and member of the original Powell Peralta skateboarding team, Caballero has fared a successful life on two and four wheels – motorcycles and skateboards feed his rebellious nature and offer freedom and thrill of the ride.

In the 1980s, Caballero, along with his teammates – Tony Hawk, Rodney Mullen, Mike McGill, Lance Mountain and Tommy Guerrero – not only pushed back the horizons of what was considered possible on a skateboard, but cracked open realms that people considered impossible. During his time riding with the elite team, Caballero invented many of the complex tricks and air variations that are still fundamental in skateboarding today. In 1987, he won both street and vert titles at the World Championships in Munster, Germany. The same year, Cab set the world record for the highest air on a half-pipe – a record that held for a decade until surpassed by Danny Way. It was no gaffe when in 1999, Thrasher named Cab "Skater of the Century."

As if centennial-legend-skater wasn't enough, Caballero has found himself flourishing in a second-act as celebrated participant in the motorcycle world – riding motocross, building vintage show bikes and even racing old Harley-Davidsons. Last year, Cab and renowned builder Bryan Thompson fabricated "The Scout," a Triumph Pre-Unit show bike. The Indian-inspired meld of British and American classics was shown at the Born Free Show and subsequently selected to show at the Mooneyes Hot Rod Custom Show in Japan. In between all of this, Cab found time to purchase the Wall of Death '44 Harley and compete in The Race of Gentlemen in Pismo Beach, California. "The quiver of pre-1947 Harleys at the gathering before the races was the most incredible sight," recalls Caballero. "They delivered my bike to Pismo and I had just two days to learn how to ride it before the races."

Recently, we rounded up five Ducati Scramblers and rode up the Pacific Coast with Caballero – touring from San Diego to San Luis Obispo and back – in search of backcountry winding roads, secluded campgrounds and outlying skate spots to session along the way. Our crew included Steve Caballero, Elliot Sloan, Fred van Schie, Nathon Verdugo and myself. The result can be seen in the video premier of Parallel, where Steve describes the connection between skateboarding and motorcycle riding. "It's freeing being on a motorcycle," says Caballero, "You can ride by yourself or in groups – like how skating is – and explore and experience nature on two wheels."



During our two-wheeled adventure along California's shoreline, Caballero sat down with Rolling Stone to discuss his affinity for motorsports, share how he financed two prized bikes by hustling online and what the future holds for the now-grandpa skateboarder.

In the video, you describe a lifelong relationship with motorcycles. What ignited your interest in bikes?
When I was a kid, I used to put parts on my bicycle to make it look like a motorcycle – a tank, front and rear shocks, and of course a playing card taped to my bike so it would scrape the spokes and make a "motor" sound. I used to ride my bike off jumps and pretend to be Evel Knievel, my hero and inspiration. So as soon as I started making money as a professional skateboarder – I was around fifteen – I bought a Honda MB5 50cc motorcycle. That was my first mode of transportation and I rode motorcycles for years before I ever got a driver's license or my first car.

What are some of your favorite bikes you’ve had over the years?
At first, I went down the path of fast bikes – a 1988 Kawasaki Ninja 250, then a 1990 CBR 600. And then pretty early on, before the whole Bobber craze, I got into British bikes. By 1992, I had a '63 BSA Lightning 650, a Norton Commando 750 and 850 – '73 and '74 respectively – and a beautiful 1959 Ariel Square Four. I sold my CBR because I was just done with going super fast and making irresponsible decisions. I had been going out to parties and clubs, drinking and riding without a helmet – immature stuff. After that, I got deep into hot rods and dirt bikes for along time until, more recently, I turned my interest back to vintage motorcycles. Anything pre-war gets me really excited.

Our first stop along our motorcycle journey up the coast was a visit to Roland Sands Design. Roland recently said that he wants to get you into Hooligan racing. Are you down for that?
I'd be down for sure. I'm a very competitive person, so now that I have that a Harley, it would be fun to participate and hang out with that crew. You can always get hurt racing – I've raced a 50 cc motorcycle and ate it. You're going fast man, and when some guy takes your elbow out when you're pinned – you high side and you're going down. Hopefully my motocross skills will translate well like they did in The Race of Gentlemen.

How did you get involved with The Race of Gentlemen?
That one just fell in my lap. I was planning on just going as a spectator, but one of the event founders, Mel Stultz, was selling his 1944 Harley Davidson used in the Wall of Death at the Born Free Motorcycle Show. I told him I would buy it if I could race in TROG and he agreed. The trick was that I didn't want to overstep any boundaries with my wife by tapping into our personal bank account to buy the bike, so I put some of my vintage skateboards on eBay to see what they would sell for – first edition Tommy Guerrero, Mike McGill, Steve Steadham, all these 80's boards. I sold six decks in twenty-four hours and raised the $15,000 I needed to buy the Harley.

You're telling me you financed your vintage Harley completely from selling skateboard decks that were buried in the back of your closet?
Yes, in twenty-four hours. The next challenge was getting my bike shipped out to the west coast and learning how to ride it just two days before the race. It was really hard because I had never ridden a Harley or operated a foot-clutch, tank-shift motorcycle. That was tricky – shifting is completely different when you're racing than cruising around. The flag goes down and you're pinned and trying to shift gears quickly – it'a easy to miss a gear. But I think people were stoked that I was out there and got really into it. I had a great time and, once I figured out some of the nuances of my bike, I won one of my races.

That's amazing. And you also built a show bike last year – a vintage Triumph. Did you hustle to build that bike as well?
I did, actually [laughs]. It's a 1952 Triumph Pre-Unit – a custom project that Bryan Thompson and I worked on for eight months and cost double what I paid for my Harley. All of the money came through hustling – artwork, art shows, skateboards. My skateboarding fans and the people who support me helped me build that bike and I'm so grateful and humbled by the support of the community. I documented the entire project on my social media – to include everyone in my journey – from the very first photo of the Pre-Unit rigid frame, to a photo of the completed bike, "The Scout" and me on the cover of Street Chopper magazine.

What inspired you to build a show bike?
Bryan is the best with custom Pre-Unit Triumphs. I met up with him and checked out some of the bikes he had built and I couldn’t resist. So I asked him to build me a bike for Born Free 8, which was an incredible challenge for Bryan, since he was already an invited builder and working on his own bike for the show. I also wanted to build something so radical, it would get noticed by Shige [Suganuma] and earn an invitation to the Mooneyes Hot Rod Custom Show in Yokohama, Japan. And it did! Shige loved The Scout and had it shipped to Japan and Bryan and I attended the show.

It sounds like all your efforts have paid off. What are your aspirations for 2017? Are you gonna build another bike?
No more bikes! [laughs]. I'm just working on getting both the Triumph and Harley street legal so I can ride them. Riding a finished bike is just as much fun as the hunt – finding parts and bringing them all together is really exciting. The smell the oil and gas burning and the sound – there's just something about that sound of a vintage Harley or Triumph that I love.

2016 was a big year in skateboarding for you as well, with the 30-year reunion of The Search for Animal Chin. What are your skateboarding plans for the future?
I'm going to stretch more and get limber enough to relearn some tricks that I lost over the years because of not being able to grab my board in certain ways. Skating isn't getting any easier – I'm 52 years old and it's hard to do ten walls without getting tired. I definitely want to stay on top of my game and progress – which for me, is relearning old stuff I used to do in the 80's. I want to continue to inspire and encourage skaters of all ages. I'm a grandpa now, so I like to throw that card around and say things like, "How many grandpas do you know that can do that!" I make fun of how old I am and I grow my grey beard out to even look older. It's just odd to me, because skating is such a young sport that we don't really know how long we can do this for. We're still paving the way for future generations.

You definitely pioneered skateboarding as we know it today. What is your fondest memory?
My fondest memory is when Stacy Peralta judged at a skateboarding contest I competing in down in San Diego. For one, having seen pictures of him in the magazines and then getting to meet him in person was incredible. And just after the contest, he introduced himself and asked if I wanted to join this skateboard team he was putting together called Powell-Peralta. That's a moment I cherish and the highlight of my entire career. I knew that from that point forward, things were going to really turn around and everything thing I had had worked so hard for was going to happen. I would get to go skate all these blooming skate spots I saw in the magazines – Big O, Marina Del Rey, Upland, Lakewood. Mostly, I realized in that moment, that skateboarding was going to be something that I was going to be doing for a long time – I just never knew it was going to be this long [laughs].

Did you eventually get to meet your childhood hero, Evel Knievel?
I did, and I never dreamed that I would meet him through skateboarding. I was entered in a street skating contest in Saint Petersburg, Florida back in 1999. It was an ESPN X Trials, a qualifier to get into X Games – I won that competition. At the time, Matt Hoffman had a collaboration bicycle out with Evel Knievel. Matt called me and told me I would have an opportunity to meet Evel at the autograph signing session. I brought a copy of the 1974 Sports Illustrated issue that featured Evel on the cover. I got to meet him and he signed my magazine and the skateboard that I used in the competition. It's just amazing to me, all these opportunities came through skateboarding – the motorcycle stuff, meeting amazing people, who I've become and what I'm about.