Jensen Callaway

By Cash W. Lambert

Photos: Leon Legot


Everyone knows Jensen Callaway. We’re sitting outside of Blueline Surf and Paddle Co. in Jupiter during peak hours, and every person that walks by has to say something to him. But this isn’t surprising, because the South Florida native sticks out – anyone who surfs the Juno Pier will attest to that. From the sand, you can see his dreadlocks and his dark skin. And his deep carves, airs, and power turns. It’s impossible to miss him. But getting a hold of him after you see him is something entirely different – the 25 year old vagabond has been booked on the pro circuit of surfing since age 13, venturing to Mexico, Scotland, Jamaica, California and Peru, just to name a few. But today, his contest jersey is dry and his board has more white space than it has in the past. But Jensen’s fine with that. He’s done it. Lived it. Surfed it.  Now, his feet are firmly planted in Jupiter. He’s been busy catching up with friends and locals, and he’s running Jupiter’s only annual grom contest. He’s happy. He’s relaxed. And he’s doing just what his tattoo says to do in uncertain times: walk by faith, not sight.

Take us back to when it all started. How did you get so involved with surfing?

When I was five, I started boogie boarding for fun like most people. A year later I received my first a surfboard from my parents. I started competing around 10, doing contests including the ESA’s and the NSSA’s. Then I stepped it up to the junior pros, and I ended up doing 25 contests per year in my teenage years, since you could do both junior pro events and WCT’s. It was a great time in my life because I had a full schedule. And my parents were great throughout the whole thing. They would pack me up and send me out to California for a month when I was 13. They had a lot of trust in me, gave me a lot of freedom, and allowed me to learn a lot on my own.

When did the contest aspect of your life stop? Last year. I only did two events, the QS in Puerto Rico and Virginia Beach. It was the first year I didn’t sign up for membership since I was 17. The problem is that there’s not very many North American contests, and in the few that do run you have to be in the top 60 just to get in. So I would be entering and paying for membership just to surf one contest. And out of region memberships are super expensive, and either way it’s hard financially, because I don’t have the sponsors that I did when I did younger. It’s something I’d have to do on my own time. It’s just a time when a lot of things are changing. Even with East Coast events. It seems like they’re dying out.

Contests are such a love hate relationship. Has this been your experience? It really is a love hate relationship. I love doing the contests, but there are times when I would call my dad and say that I didn’t want to another event. I was burned. But he’d say don’t – it’s about having fun. That’s why you start in the first place, and there’s no reason to get burned out. He’s right, because the traveling is always fun. It’s always a mission. There’s times when I’ve been completely over contests but then I’ll see some friends surfing and I’ll immediately just want to be surfing. That shows me that I’ve still got that competitive bug.


Since you don’t have that constant stress of contests, does it feel like a weight’s off our shoulders? It’s nice to know that I don’t have to do events just to please my sponsors. It’s helpful that I don’t have to stress to get money for the contests, too. That was hard, really hard. Because you start breaking down everything financially, and you realize that just to make your money back, you have to make a certain number of heats. And if you don’t make a heat then you lose it all.

Out of all your traveling gigs – what was one of your favorite? Which one stands out? I have two. Peru, because I loved it. There’s tons of waves, and  people think there’s only left point breaks, but that’s not true. There’s rights, too. Great waves 300 days of the year. And Salina Cruz in Mexico. I surfed there in 2006, which was before the spot blew up. I went down there with the Billabong team and Dino Andino and Mike Parsons. We had a whole compound: cars, jet skis, everything. At that time, there weren’t even people, just goats on the beach. The waves haven’t changed there since, but the number of people have.

Even though you’ve seen so much of the world, you still call Jupiter home. Why?

I love it here. Everyone always said that I should have moved to California, but it’s just a big rat race there.  Here, you can surf in your boardshorts, and the water is clear. You’ve got it all: the ocean, fishing, hunting. Where else can you jump on a boat and go to restaurants, or hangout on the sandbar on the weekend?  No matter where I went, I always looked forward to coming home.

You love it enough to start your own staple here, too. Tell us about the contest.

There’s not really that many contests that the little kids here can do. There’s ESA’s, but nothing strictly for the younger kids. So 2011 was the first year we did the Jensen Callaway Halloween Grom contest. I went to my sponsors and they were pumped on the idea. All divisions are 17 and under all the way down to 8 under. The first year over 40 kids came out, and last year we had 60. We went all out, getting shirts, doing some graphic designs, and I even got the oversize checks to give out, because when I was a kid that was something I always wanted to win. First contests are always special – I definitely remember mine.

You always stick out no matter where you go. Even just sitting here at Blueline. Maybe that’s because of the dreads, and two tattoos? I actually cut my dreads off in high school and I was unnoticeable to even my closest friends. I’m Cherokee Indian, which is why I have this tattoo of an Indian on my arm. And the other one is one of my favorite quotes – the tattoo says walk by faith, not by sight. It’s from an old Indian poem that someone sent me. It talks about a man who tests his son by bringing him into the woods blind folded all night. He isn’t allowed to take it off until morning, and his dad tells him that he’s leaving, but actually stays by his side the entire night. When the morning comes, the boy takes off the blindfold and sees that his dad didn’t leave him. To me, it just means to not be afraid just because you can’t see things in front of you. Because if we have faith, anything is possible.


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