Captain Plooby began sailing the seas of the earth since he was 14 years old alongside his father, "Captain Blackeye III", who also owned a restaurant on a very small island in the Bahamas called "The Flying Dutchman's Graveyard Diner", which still runs today by Captain Plooby's brother Captain Crampton. In Mr. Fireman Crusaders of Fire, Captain Plooby reaches shore of an island, where his henchmen rob a electronic store and steal many electronic devices, including a TV. Plooby, who has never seen such a device before, watches it and sees a commercial made by Mr. Fireman, who announces to the public the chance to line up and receive a small portion of Buzz Tarco's lottery money during the taping of an episode of The Morning Show! With Mr. Davis. Plooby, hearing about the money, sets sail for Mr. Fireman's home town to seize the "treasure". However, by the time they get there, Buzz Tarco has been taken away to boot camp along with the firemen, and arrives there to find that the money is stowed away in a checking account. As a result, he kidnaps Buzz Tarco's daughter, Delilah, as well as Mr. Ambulance, who was visiting Tarco's apartment at the time of the kidnapping an accidentally admitted to knowing of the money's location. The two are taken aboard Captain Plooby's ship, where Tarco is assigned by a ransom note to hand over the money to him within seven days, otherwise, his daughter, as well as Mr. Ambulance, will walk the plank. The ransom is forwarded to the boot camp's mail room by the mailman, where the sergeants believe the letter to be a ploy to bust Buzz Tarco out of prison (by this point, Tarco has been incarcerated for "refusing to follow orders"). Mr. Fireman and his co workers, however, believe the note, even though nobody else does. He logically concludes that they could either break out of boot camp and risk some embarrassment of being wrong, or stay behind in boot camp and possibly let the two die. The Crusaders of Fire successfully break out of boot camp and manage to travel to Captain Plooby's home location due to the address being written on the letter. Meanwhile, Captain Plooby's crew finds a robotic body at the bottom of the ocean, which is later revealed to be Striktrus, Clonebot's son, who has been lost at sea for 15 years. Days later, the "Crusaders of Fire" finally make it aboard Captain Plooby's ship, where they successfully free Delilah and Mr. Ambulance (although one of the Crusaders of Fire, Ryan, dies in combat, and his body is buried at sea from the ship). Captain Plooby, having been knocked unconscious from the battle, wakes up and finds that Striktrus has also woken up, having been discovered by Wonka during the rescue mission aboard the ship. When Striktrus learns that Wonka is partially responsible for killing his father, he teams up with him to seek retaliation on the Crusaders of Fire, as Captain Plooby also wants to seek retaliation on the firemen for foiling his ransom plan. The Plooby returns to Mr. Fireman's home town once again along side Striktrus. The duo, along with Plooby's numerous henchmen, form an army and declare war on the Crusaders of Fire. The battle continues for a length of time until Sergeant Jones, the sergeant in change of the firemen and Tarco back at boot camp, makes a surprise appearance with an army of his own and aligns with the Crusaders of Fire. The battle continues until the Crusaders of Fire achieve victory. Striktrus, and all of Plooby's henchmen are killed in battle, and Captain Plooby is arrested after the battle comes to an end.
Captain Plooby is portrayed as an completely generic stereotypical pirate, despite that all of his henchmen are portrayed as much more realistic portrayals as pirates. He runs a pirate ship known as "the Great Bessie!", which is, in reality, a modern cargo ship that Plooby converted to look like an old fashioned pirate ship. Plooby, however, refuses to accept this as fact, and insist that everyone refer to his ship as an "old fashioned pirate ship", threatening death on anyone who defies this. Plooby also insists that nobody call him "sir", and that everyone refer to him simply as "Captain Plooby".