George was a pirate, but he wasn’t a very good pirate.
He managed to get taken captive by The Dread Pirate Roberts.
“My real name’s Westley, and I’m in a bit rushed,” said Roberts. “I need to get back to Florin to rescue my true love from kidnappers. Mind taking over things for a while?”
George agreed, and Westley trained him as quickly he could.
“Good luck,” said Westley, handing off the mask, and rowing away in a lifeboat.
George waved, put on the mask, and took command of the ship.
Which smashed into The Cliffs of Insanity and sank.