Creature sent David Gravette and Taylor Bingaman. Sk8mafia sent Wes Kremer and Tyler Surrey. Habitat's Marius Syvanen came as a designated hitter for any injured or sunburnt member of either team. The battleground was historic pirate territory—Grand Cayman and its massive Black Pearl skatepark. Did these guys have serious competition, or just party it up in paradise? You decide.

Filmed by Chris Ray.

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Huge thanks to JR, Skate Cayman, Treasure Island Resort, Billy Bones Bar, The Brick House & Brew House, and Calico Jack’s.