The Wooden Elephant first appeared in the episode "The Elephant Surprise!", While Jake and his crew are playing volleyball, Cubby discovers a large wooden elephant as a gift for the crew. Jake seemed to be curious along with the rest of his crew-mates as to which of there Never Land friends left them such a gift. Unknown to the young pirate team Captain Hook and Mr. Smee were hiding inside of the elephant in order to gain access into Jake's treasure room. Once Jake and his crew place the elephant inside the treasure room. Soon Jake and his friends hear Bucky's bell alerting them its lunchtime. As Jake and his mateys leave for lunch, Hook and Smee reveal themselves and begin stuffing the elephant with all the toys. Jake and his crew soon hear something strange coming from the treasure room and rush to find that the wooden elephant is rolling away. Jake and his crew soon track down the elephant through Pirate Island. As the young pirates roll the elephant back to the Hideout, Jake and his crew soon hear voices coming from inside the wooden elephant and discover Hook and Smee inside with the toys from their treasure room. Hook soon gloats about the sneaky plan and claims to take all the toys and the wooden elephant as well. Jake and his crew remind Hook once you give a give just can't take it back which Smee also agrees with them. Hook refuses to give up the treasures only to be blasted skyward with Smee from the erupting geyser from Geyser Beach sending the villainous duo crashing back to the Jolly Roger. The Wooden Elephant is last seen back in Jake and his crew possession placed once more into the treasure room with the rest of the toys.
The wooden elephant is a reference to the Trojan Horse:
Captain Hook and Mr. Smee act as the Greeks in the statue.
Jake and his crew accepting the wooden elephant is like the way the Trojan accepted the Horse as a gift.
The treasures being stolen are like the Greeks taking over Troy (Jake's treasure room)
Hook and Smee inside the Wooden Elephant
Jake and his crew discover Hook and Smee inside the elephant.