Desperate to get the money to save his ship, Long John agrees to a plan another pirate recommends to steal Spanish gold. But the pirate turns out to be just as much of a liar as was the last time Long John met him.
Arrogant Lord Ellington is put in his place by members of Long John's crew, and gets the Cask and Anchor shut down in retaliation. But Long John smells a rat, and sets out to bring down Ellington and reopen Miss Purity's Inn.
Miss Purity and Long John decide Jim should be sent to a private school after he causes trouble at a local birthday party. But things become worse then Jim's roommate is the same boy who actually caused the trouble at the party.