Baloo and Becky go shopping and Kit is left with the responsibility of babysitting Molly. Kit has his hands full, until Molly's favorite radio program, 'Danger Woman,' comes on. During the commercial break, Molly wants ice cream. They were instructed not to go further then the corner store. Meanwhile, Don Karnage sends Mad Dog and Dump Truck to steal goods from Cape Suzette via sub. When they cut through the net that keeps all sea creatures from entering Cape Suzette's harbor, A giant squid follows them. When Molly's wagon rolls all the way down to the docks, Kit asks Molly not to tell her mom how far away they strayed. However, Becky heard everything and told Kit that he was reckless and irresponsible. But when the apartment building is attacked by the squid and the pirates on the loose, Kit's job of protecting Molly is far from over.

Baloo is lost at sea while attempting The Master Run. Turns out Don Karnage has devised a plan that fools all pilots into thinking they are flying upside down, thus causing them to fly up (or down) into the ocean. When Karnage reads Baloo's 'Greatest Pilot in the World' trophy, he mocks and belittles him into depression. Kit tries to think of a way to get out of this mess, but Baloo is wallowing in self pity. When Kit finally gets everyone free, they are chased by the pirates. Kit makes a suggestion that will help them cripple the pirates planes, but all the other pilots say that Kit's plan won't work. Finally Baloo breaks free of his self loathing and stands up to the others telling them that Kit is the best navigator he ever had and if he says the plan will work, then the plan will work.