Among his highlights, Caballero was part of Stacy Peralta’s famous Bones Brigade skate team during the 1980s that featured some of the era’s best skaters. And he also is known for creating many popular shoes with Vans like the Half Cab, which turned 20 in 2012.
Tell us about your first Vans shoe.
It was a huge deal. I was the first skateboarder to release a shoe in the U.S. It was a huge success over the years. We redesigned the shoe in 1992 — that was the release of the Half Cab — and made it a mid-top. Once we did that, it blew up and everyone was wearing that in the ’90s. Now, it’s a mainstay in the Vans Classics line.
What has your relationship been like with Vans?
Just like personal relationships, they take work. There was a time where I had to take a 6 percent royalty cut to keep their program going. It’s all a sacrifice, and there have been key people who helped me maintain my loyalty. One of them is Steve Van Doren. He’s just been a great supporter and he’s always had my back.
Do you have a favorite memory from being on Stacy Peralta’s team?
Releasing our video [in 1987] called “The Search for Animal Chin,” where we did a storyboard line about searching for this legendary skater. Stacy [Peralta] decided to write a story and we traveled to Hawaii, and Bakersfield and San Francisco, Calif.; we built a huge ramp. We were at the top of our game. It was kind of cheesy but fun at the same time — it just showed our personalities. Something we did for fun became legendary and an icon within our industry.
How has skateboarding changed?
It’s looked at a little more seriously as an occupation. A lot of guys have their own training facilities. We didn’t have that back then. We just skated whatever came our way. Skateboarders didn’t own homes back then. When I started there weren’t public skateparks — they were all privately owned by investors, doctors and lawyers.
What does Vans’ 50th anniversary mean to you?
It’s a celebration of creativity and passion. They just represent the soul of skateboarding. They stuck to their roots, and being in business for this long shows their loyalty to our industry.