Captain Crook showed up as the main villain in the episode "Viva Las Lapras," a pirate captain who makes his living poaching Pokémon. He's the kind of guy who doesn't care who gets hurt—not his crew, not his own Pokémon—as long as he gets what he wants.
His typical operation involves his first mate Ghali spotting targets from the ship, then Captain Crook firing cannons loaded with Poké Balls containing Tentacruel to capture wild Pokémon. When he needs actual firepower against authorities, he switches to regular cannonballs instead.
Ash and his friends ran into him when they spotted a school of Lapras near Tarroco Island—Crook's next target. Misty, unsurprisingly, wasn't having it. Her Water Pokémon destroyed his ship and tied up the crew with rope, leading to Captain Crook and his entire gang getting arrested alongside Team Rocket. Misty then freed all the Tentacruel he'd been using as weapons.
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