He glides through the years and generations with the absolute “lightness of being”. Name, icon, legend, culture – these words barely scratch the surface when we talk about skateboarding.

Seriously, we swear we want to discuss skateboarding. But then we realize that Caballero is like the Caterpillar in Alice in Wonderland: an oracle with answers to everything.

Life, art, love, the essence of being human – it all unfolds in less than an hour. We can’t get enough of asking him questions, and we never tire of hearing his insights. A shy shapeshifter, he excels in every arena: pro skater, artist, musician, fashion icon, rider.

Known to the world as a skateboarding icon, labeling him just that is an understatement. Caballero is much more – he’s a multifaceted artist.

Today, he exhibits his works in art galleries and shows, visually expressing everything that represents him, creating a deep connection between himself and his fanbase. What we know for sure is that Caballero knows only one way to do things: by being the best version he can be.

What an insanely talented human.

It’s hard for us to imagine him as an introvert, yet Caballero’s story is that of a shy, unpopular teenager. And yet, Steve himself admits: «You should have see me when I was a little kid in highschool. When I was in a group of people, my lips were just quiet».

You just need some attitude

Steve Caballero: «I grew up a very shy boy; I was very antisocial at school, didn’t go out with any girls in hightschool. I focused only on skateboarding; and that’s why I was able to make a profession out of it, make achievements and become famous. Because I put a lot of time an work into my art. Because I feel like skateboarding is an art form».

This makes us think about how, often, every form of art stems from a deep introspection.

Steve Caballero: «Everybody has a different way of trying to control their environment, trying to do what makes them happy, trying to survive. It’s a dangerous world, I’m not gonna lie, but it’s not a world that I wanna live in fear».

In 1980, the Caballerial marked a turning point in the history of vert skating, which later blended into street style. A fakie ollie 360 debuted during one of his early competitions – a trick that took his name and skyrocketed to fame thanks to one of the most iconic brands in skateboarding history: Powell Peralta.

The rest is history: the Bones Brigade, a revolutionary team of skaters that forever changed mass culture. The Brigade, consisting of kids aged 11 to 15, introduced legends that would resonate for generations: Tony Hawk, Steve Caballero, Rodney Mullen, Alan Gelfand, Lance Mountain, Tommy Guerrero, and Mike McGill.

An incredible talent and a reckoning with shyness, anxiety, and unease – a world where to grow, you must push beyond the limits of your fears. You grow when you put yourself in a position to be judged. And this is frightening.

Steve Caballero: «I kind of opened up a little more when I started associating with a lot of people and having to deal with the anxiety and stress of performing in front of a crowd. But the more you force yourself into this arena, the more you get used to it, and the more comfortable it becomes. But if you are shy and scared and stay away, you’re never gonna grow up. You’re never gonna learn».

Steve Caballero: «You have to put yourself in vulnerable situations where people gonna judge you and criticize you, but you’ll take it lightly and try not to let it affect what you’re passionate about. And what I was passionate about was skateboarding».

The first lesson we learn from Steve is a lesson in courage. If you are brave enough, people will understand what you are passionate about.

Steve Caballero: «My passion was skateboarding, and I wanted to become the best skater I could ever be».

Long story short: you just need some fu*king attitude. What is attitude? A fire that burns within us.

Superheroes against the municipality

This summer, I learned what attitude really means. At the skatepark, I met O. A 6-year-old standing around 130 cm tall. He arrived from Argentina with his mom, who moved to Italy for work. We found ourselves at the skatepark in Iglesias, nestled within a community sports center known as ENNE2 – a long-sought gem for generations of skaters who, since the 1980s, had to settle for grinding on railings, benches, and navigating run-ins with the municipal police.

Reasonable doubts lead us to believe that, unlike the lions and gazelles in Africa, at a certain point in Iglesias, everyone became a bit tired of running: the skaters, worn out from their relentless escapes after grinding the walls and benches of the town square, and the police, exhausted from their efforts to catch them and make them stop.

As the Meganoidi sang: «Superheroes against the municipal police».

Even though it was O.’s first time on a ramp, he didn’t hesitate for a second. He launched himself straight onto the steepest ramp and fell.

He smiled: «Wait, I’ll try again». And he did. He kept trying until he nailed it. His smile is something I will never forget. He may not realize it yet, but that day was incredibly inspiring. I understood what attitude means. Attitude is trying for the thirty-first time after failing thirty times before because it’s in your veins. Because it belongs to you. Because attitude transcends results. It’s something you were born to do. It matters in skating just as much as in life.

Steve Caballero: «You know, what I’ve learned in skateboarding is that you have to fail to succeed. That means you’ll fall, you’ll fall, you’ll fall. You get hurt, you heal, you get hurt, you heal».

Steve Caballero: «But eventually, when you work super hard, all that work pays off when you finally land the trick. And you know, you smile; you bring attention to yourself for completing something that you worked so hard for. And It’s a good lesson in life. What skateboarding has taught me is that everything in life revolves around pain and suffering, you know, and you have to understand that if you want to be able to go to the next place to progress and be successful. A lot of people don’t want to go through that, so that’s why they are not successful».

We delved into discussions with Steve about skating and life. We talked at length about wrong choices, mistakes, limits, and those moments when we strive to push our boundaries. We explored the human experience, emotions, and relationships.

Caballero embodies inspiration and energy. At one point, we lost track of whether we were there to interview him or if we were in a therapy session. We joked about wishing Steve could be our therapist. He laughed heartily as we imagined him channeling a bit of Jack Nicholson from Anger Management.

Steve comes through loud and clear, reaching deep into your soul. He inspires us to be better: better professionals, better people. Beyond falls, beyond mistakes.

Yesterday is history.
Tomorrow is a mystery.
But today is a gift. That’s why it’s called the present.

Kung Fu Panda

We set out to discuss 1980s California, the Bones Brigade, and skateboarding like we’ve never known it. But Steve imparted an invaluable lesson: the present is our greatest treasure.

Steve Caballero: «I’m grateful for where I come from. But I don’t like living in the past. I like to live. I like to learn from the past. But I’m not one of those people who will tell you, ‘Oh, skateboarding was much better in the ’80s, ’90s, or 2000s.’ No. It’s great right now. It’s the best it has ever been».

Like all the greats, he hits us with a truth that sticks: the present is everything.

The past shows us the way, but it’s in the present where we shape our future. If you get that, you’re already ahead of the game.

Thanks, Steve, for being so humble and real. This talk just shows us why the ‘greats’ are just that.

Silvia Scarpa

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