Captain Plunder

Captain Plunder is a fictional character (a sometime-villain, sometime-antihero), created by Nigel Kitching and Richard Elson in Sonic the Comic. He leads a band of "Sky Pirates", who resemble stereotypical buccaneers in every way, save that rather than sailing on water they travel using a flying ship. Plunder himself wears a traditional eyepatch, a black hat, and a wooden leg (albeit with a wheel attached to the end). Although he first appeared as an antagonist in stories featuring Sonic the Hedgehog and his allies, the character soon became popular enough to receive his own stories.

Although Captain Plunder is highly feared by the people of Mobius (most of whom have never met him), he is less respected by his peers. Several encounters with Sonic and his friends have shown him to be little more than a nuisance, and he has a bad reputation among other pirates. Most sensible pirates steer well clear of the dunderhead who has earned himself a place in Queen Zorabel’s bad books.

His second-in-command is a reptilian poltergeist called Filch, with a large hole in his head; Plunder shot him dead for taking the last biscuit without asking.

Pirates of the Mystic Cave
Sonic first met him when he kidnapped Amy Rose and held her for ransom at his base in the Mystic Cave Zone, but as the two groups started fighting Amy suggested they formed an alliance: the Freedom Fighters could do with help and they could tip of Plunder if they heard about Doctor Robotnik’s expensive cargo. The successful arrangement worked for a while until Porker Lewis accidentally told Plunder where Sonic had hidden the Chaos Emeralds. Plunder and the Sky Pirates disappeared to collect the emeralds, with Sonic in hot pursuit. In the ensuring battle, Plunder successfully managed to walk away with all the Emeralds. However, the Chaos Emeralds temporarily absorbed all of Plunder's negative energy, as well as that of the entire crew; this made them "mellow out" and turn into hippies, allowing Sonic to easily retrieve the Emeralds.

Arrested
Sonic gave Plunder information on Robotnik just once more. Plunder and his crew successfully robbed Doctor Robotnik’s luxury airship, the Roboticus, only for Plunder to be accidentally left behind. Plunder was given a show trial and sent to Highview Corrective Centre's dungeons until he could be hanged. Plunder was chained next to a black cat called Simpson, who was capable of altering reality for comical effect (a parody of cartoon cats such as Felix the Cat and Stimpy). Together they managed to escape into the sewers - simultaneously, Filch led Plunder's crew in a rescue attempt, and both groups unwittingly passed each other. Plunder returned to his ship to find his entire crew (bar Filch who could escape easily) was now being held prisoner in Highview. Rather than go to rescue them and thus have to share the Roboticus booty, Plunder promptly decided to get a new crew.

The Floating Island
For years, Plunder had had a chest full of ancient scrolls on the Floating Island; once it was discovered the Island really existed, he headed to the Sandopolis Zone with his new crew to loot the Great Pyramid. Plunder and his crew ran afoul of Sonic and Knuckles the Echidna, but managed to avoid them while they were preoccupied fighting the pyramid's giant stone guardian. Free to loot the Pyramid, Plunder and his men were ill-prepared when the lights went out, causing the Sandopolis ghosts to arise and attack. The pirates barely escaped the pyramid but had left the treasure behind; irritated, Plunder left the island and lied about the number of ghosts there'd been to his crew.

Some months later Plunder and his crew landed on the Floating Island when trying to steal the Tantaragor Idol, a powerful teleportation device, from the mysterious Ghost Ship. Plunder bribed Knuckles into assisting with the promise of his ancient box of scrolls, but didn't mention the ship was inhabited by powerful alien slavers called Tantaror. The pirates boarded the ghost ship and Plunder managed to obtain the Idol, only barely escaping the Tantaror thanks to Knuckles and leaving several of his crew behind. Returning to Scourge Bay, home of all Sky Pirates, Plunder and Knuckles clashed over returning to free the Tantaror's slaves until Zorabel the Pirate Queen arrived. She demanded Plunder leave Scourge Bay before the Tantaror arrived looking for the idol, but the building they were in was suddenly teleported to another world; the slavers were heretic Tantarors and the idol was in fact a trap designed to capture them by supreme Tantaror Ekkletos. Plunder had to watch as Knuckles was sent to the Ghost Ship to free the slaves and help capture the heretics. In the end Plunder was left with no Idol and Zorabel forced Plunder to give Knuckles the scrolls.

Later solo appearances
Using a Star Post attached to the wheel, Plunder and his crew arrived in the Special Zone to press-gang a few more members. The crew captured Proctor Speckle, only to make him walk the plank when he stole from Plunder's private chocolate stash. It was then the pirates discovered he was the alter-ego of the murderous Mr Fry, who emerged from the ocean with a dead shark in his jaws. Luckily it turned out Mr Fry wanted to join Plunder's crew; unluckily, the serum that created Fry had spilt into the ocean and created several "super sharks". Plunder took matters into his own hands and pummelled the sharks unconscious with a giant hammer, but Mr. Fry had vanished - and so had Plunder's vintage rum truffles, floating back to shore with Speckle.

Plunder returned to Scourge Bay, failing to press-gang anyone until Zorabel hired him to join her on a quest for the treasure of King Akotek along with her daughters, the Spice Maidens. The crew set sail and after a long adventure they eventually found the treasure. Unfortunately, it turned out Zorabel hired Plunder because the treasure was cursed and she wanted him to contract the curse instead of her. Now doomed to spend the rest of his life cursed by misfortune, Plunder barely made it back to the ship in one piece. He then lost his share of the treasure overboard, where it disrupted the shield around the ship - at the exact moment when Captain Tiberius, an old rival of Plunder's, finally caught up with him. Now with a destroyed ship, Plunder and his crew were left stranded on a desert island. Plunder was last seen sitting underneath a coconut tree cursing his bad luck, with coconuts about to thwack him on the head.

Sonic the Comic Online
In the unofficially official fan-comic continuation, Plunder made a cameo appearance in #239 - interviewed by a documentary crew, he claimed he and Sonic were close-knit allies. He was still cursed. Filch made an appearance of his own in #242 as part of a team Tails had assembled, and his dialogue suggested the Sky Pirates themselves are still active.