An intrigue involving the election of class president reminds Wishbone of the twin brother of King Louis XIV of France who must decide if he should risk everything to escape his iron mask and trade it for the king's crown.
Because Wishbone keeps getting interrupted while trying to take a nap, he begins thinking about Rip Van Winkle and finds himself in Rip's shoes, finally waking to a changed world.
While hunting for treasure in an old barn with Joe, David and Samantha, Wishbone imagines he is orphan Jim Hawkins from "Treasure Island", fighting pirates and searching for buried treasure.
When Joe Talbot's backpack is confiscated, Wishbone and Joe must confront a scary neighbor who owns a big mean dog that reminds Wishbone of the monsters defeated by Beowulf.