After more than 30 years in the sport, Phillip Berry is taking his passion for skateboarding to the next level by officially joining the professional ranks.
Antilles Skateboards, a Caribbean skate crew, announced the pro debut of the 50-year-old from Savannah, Bodden Town, who they described as “the cornerstone of the Cayman skate scene over the last 30 years”.
More than a title
Berry, who officially turned pro on 25 Jan. of this year, first picked up a skateboard at age 14 back in 1989. For him, reaching this milestone is less about commercial success and more about a lifelong dedication to the craft.
“For me, achieving the status of pro isn’t about chasing a corporate sponsor, signing a contract, or waiting for a board company to put my name on a piece of maple. At this stage of my life in skateboarding, the definition of pro shifts from a commercial title to a deeply personal, internal standard of excellence,” said Berry.
“Personally, being pro means something far more resilient and rare. Skating for decades, the ultimate pro contract is written with my own body. It’s no longer about jumping down massive stair sets just to get noticed; it’s about the absolute distillation of style and control,” Berry added.
Additionally, he views this new milestone as “living to bridge the history of the sport within your local scene, whether that’s guiding the next generation or simply preserving the memory of how the local concrete culture has evolved”.
Dimitri Rohan, owner of Antilles Skateboards, said, “The consistency and community Phillip has helped foster has been impactful not just for me but many others.
“Being pro is a major accomplishment, but, for a humble guy like Phillip, it’s probably just another Friday at Mariners Cove in Spotts.
“In all seriousness, he’s been super appreciative of this and has been a great way to confirm all the great things he’s done and earned in the right way,” Rohan added.
Reflecting on the earlier days of skating in Cayman, Berry described it as “a lot of fun” but also shared one of the challenges.
“One of the biggest hurdles was learning new tricks, but having to wait to see how the trick was done by watching VHS tapes. This meant rewinding a lot just to see the trick step by step then going outside to try it,” Berry said.
He added that one of his biggest influences in the sport during the early 1990s was a Caymanian named David Evans.
“David was living overseas but came home. When I saw him, I was so happy to skate with a pro. Once he introduced himself to me, we started skating together. I fell in love with skating and the rest is history,” Berry said.
Pro status
Unlike skaters who chase trophies on the stadium circuit, Berry is a video part skater, meaning his focus is on creative expression, style, and filming dedicated video segments rather than structured contest runs.
“The process to turn pro is comprised mainly of two pathways: the ‘part’ route and the ‘competition’ route,” Rohan said.
“Putting out parts is simply making skate videos, similar to a musician making a demo to get a record deal. The parts you put out get recognised by brands and they may want you to do the same for them once sponsored. If they are successful, as well as among other things, the path to ‘pro’ can become a reality,” Rohan added.
Berry’s pro debut is being celebrated with his very own limited-edition, numbered signature deck from Antilles Skateboards.
Rohan confirmed that 26 numbered decks were released, with “only a handful” remaining.
“Berry’s first pro board is a reference to the first board we ever released, which was the Corrugated Iron Deck. Growing up in the Caribbean, we aren’t strangers to the difficulties of relying on planes, ships and, especially, the containers to bring our wants and needs,” said Rohan.
“In 2019, rough weather sent some containers crashing into the water from the port of George Town. As dramatic as that was, the debacle was handled quickly. The imagery … was the reference we reworked into our first board and tee graphic. These graphics are staples that we always call back to,” Rohan added.
His pro debut coincided with the release of the film “Paradise Papers Volume 4,” which premiered at CAYFEST, the CNCF theatre, and during Cayman Art Week at Mutiny this year.
Rohan said that the film “highlights the past, present and future of Cayman Islands skateboarding where we learned skateboarding runs deeper than we thought during the editing process, like David Evans or the pool skating sessions at the former Treasure Island Resort post Ivan”.
“Being a part skater, we’re working on Phillip’s new pro part and new board for later this year. Some other events we have slated for this year is the continuation of our island tour showing our 4th volume of Paradise Papers, which was also Berry’s pro debut part,” Rohan added.
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