Grim Buccaneer

Many pirates who sail the Never Sea have heard of the tale of the Grim Buccaneer's wicked ways. Legend tells the Grim Buccaneer used to be first mate to Captain Colossus, one of the most famous pirate captains to ever sail around Neverland, with his ship having 100 sails while being named the mighty colossus after the captain himself. That was before he turned bad, betraying his captain and subsequently being cast away. Interestingly, Colossus himself disappeared shortly afterwards while working with King Neptune to take down a fearsome sea serpent known as the Strake. The mighty colossus sunk that very day, leaving a mystery that wouldn’t be solved until years later, when the young captain Jake began to rise to power, using a magically enhanced cutlass to raise the sunken ship from the depths of the ocean. The ship was utilized in a close battle against the jealous Lord Fathom, an evil mer-wizard desperate to take over the Never Sea, having once been a close advisor to King Neptune himself. Interestingly, this makes him and the Grim Buccaneer very similar in their motivations. However, most of the tales surrounding the Grim Buccaneer mention little of why exactly he became sinister. Only that is he sinister, while the Captain was a good man betrayed by his first mate. The reality of the situation was that Captain Colossus, much like many others in Neverland, was an idealist, seeing himself as a force of unconquerable good and selflessness, as in a place where nobody truly grows up, things tend to revolve in black and white. He saw the Grim Buccaneer as resourceful, intelligent, and charismatic, though a bit lacking in his moral compass. However, due to his belief that the good outweighed the bad in him, he kept the Grim Buccaneer on as his first mate. Not only that, but he saw him as his own son due to his deep seated paternal nature, which made the betrayal hit much harder for them both. The betrayal occurred immediately before Colossus was set to take on the Strake, as the Grim Buccaneer suspected that the sea serpent was too risky of an opponent, and that if King Neptune himself needed help from mortals, than defeating the creature was a lost cause. However, Colossus sought to ignore his warnings, more than happy to focus on doing what he could to help Neptune at any cost. In other words, to Grim, Colossus was willing to sacrifice their safety just to blindly follow someone into the unknown. What followed was an intense argument that led to Grim abandoning Colossus to whatever fate would await him. That fate being him disappearing for long enough that Grim thought he couldn’t possibly be alive, only to eventually show up as a very frail man, and a mere fraction of the legend he once was.

Overall, Grim is very ambitious and self-centered. The self-centered part became much clearer after the mental wound Colossus created in him. Grim genuinely wanted to remain by his side, as having a parental figure in a place as strange and mystical as Neverland was a grounding force. However, he couldn’t risk being lost to the waves just because his Captain wanted to go down with his ship. Instead, he wishes to be Captain of his own ship with his own rules, and his own autonomy. His main goal now that the mighty colossus has resurfaced is becoming the captain of it, since he believes the ship deserved to have him as its figurehead from the very start. He will step on anyone to achieve his goals including his own allies. He is calm and calculating but can lose his temper when things don't go his way. However, he is immensely intelligent, devious, cunning, and scheming. He can think on his feet, deduce correct facts from very little clues, adapt his plans to the situations at hand and devise nearly flawless schemes since he is an expert at creating traps and illusions. Grim's only moment of hesitation is during "The Legion of Pirate Villains", where Captain Colossus confronts him as an old man, saying that he once trusted Grim like a son, leading Grim to become somewhat troubled. However, he quickly recovers, believing Captain Colossus was merely trying to trick him. And rightfully so, considering how long it had been since they had seen each other. He also has an intense rivalry with Captain Jake despite Jake being only 10 years old, with his crewmates Izzy and Cubby being around the same age. This is probably because Jake’s crew are consistently seen in Neverland as a force of good by most people, just as Captain Colossus himself used to be, and it really doesn’t help that they have laid claim to Colossus’s ship, and have prevented him from re-possessing it on multiple occasions. This has created a painful jealousy, almost to the point of frenzied bewilderment as although he left Colossus behind, he was still the most legitimate heir to the title of Captain, not some kid pirate with a penchant for being adored due to being the bravest and the kindest pirate around. That being said, Grim doesn’t hate Jake for personal reasons. He actually thinks Jake can be quite bold and fierce when he wants to be, which is exactly what he admires. Rather, he hates Jake because of how the Colossus somehow was simply summoned by the boy’s sword, and even when Jake learned who the ship belonged to, he refused to give it up to the person who truly deserved to have it. On another note, Grim finds some of the sea shanties about him sung by the pirates Sharky and Bones to be annoying and a misrepresentation of his motivations, particularly since the shanty the duo has sung goes like this: “watch in the shadows for a darker shadow, of the Grim Buccaneer. They say by the time you blink your eye, he disappears. Just get one look, and he’s gone that quick, he’s nowhere near. He’s a phantom in the rigging, shrouded in swirling smoking fog. He’s a no-good mutineer and he’s a treacherous scurvy-dog!” Needless to say, the Grim feels disgust for the slightest implication he was the one who betrayed Colossus, as to him, he was the one who was betrayed by someone who valued optimism and pure heroics over acting with sensibility.

Appearance wise, Grim is a tall and slender pirate who has short brown hair and sideburns, with a silver earring on each one of his ears. His eye color is unknown, since his pirate hat creates a permanent shadow over the upper part of his face, though his eyes are most likely green or brown. His attire mostly consists of green clothing, as he wears green gloves, pants, and a green shirt with yellow buttons. His other dominant color is black, which his cape, hat, and boots are. He also wears a brown belt with a silver buckle, and he also has a silver clasp on his cape with a black skull. He’s almost always shown smiling when he’s trying to be charismatic, though he is definitely capable of breaking his smile to showcase frustration, disappointment, surprise, or any other host of emotions.

Skill wise, Grim has demonstrated amazing cleverness, as he has shown feats of being able to outsmart enemies multiple times. During his debut, he showed that he was capable of evading capture from Jake and the other pirates despite being greatly out-numbered and over-powered. In The Legion of Pirate Villains, he was quick to ally himself with the other villains into forming his legion to not only locate Colossus's legendary treasure but also defeat their common enemy Captain Jake and his crew. Grim is also very fast and agile, and he possesses good reflexes. He is able to hide into the shadows and can conceal himself quite easily. The only person who can keep up with him is Captain Colossus himself once his strength was restored. Swordsmanship: Grim has demonstrated some swordsmanship abilities, though his primary weapon of choice is a crossbow. He also likes to use smoke as a concealment device, giving off the illusion of teleportation.

His main interactions with Jake and his crew come from shortly after he realized that somehow, the Colossus was back sailing on the open sea. He snuck aboard the Mighty Colossus and began abducting the various members of Captain Jake’s crew from the shadows. He later reveals himself to Captain Jake, and a sword fight commences. Grim soon gets the upper hand due to his underhanded tricks and deep knowledge of the Mighty Colossus. Grim then locks Jake and the others down within the holding cell holding them prisoner, plotting to abandon them all on Pirate Dread Island just as he abandoned Colossus. Once at the helm of the Mighty Colossus, Grim savors his victory, and the glorious sensation of being the one to finally control the ship that should have been his. This is short-lived when Jake and the others manage to escape and confront Grim. Grim then attempts to flee and gets captured by Jake and his crew in a net. Ironically, Jake decides to send Grim to Pirate Dread Island, as he thinks it would be the perfect place to keep him from causing trouble in the future. Grim, however, manages to break free and swears he'll return more powerful than ever and that the battleship will become his, before vanishing in a cloud of smoke.

The Grim Buccaneer reappears as he pursues Captain Colossus's pet Fire Bird, Wildfire who has been searching for Jake and his crew to help Colossus, who was revealed to be marooned and severely ill. Grim summons three sinister pirates, ShiverJack, a pirate with potent ice powers who wishes to freeze all of Neverland, Doctor Undergear, who is obsessed with creating pirate-related technology, and unintentionally, Captain Hook to form the Legion of Pirate Villains. Captain Hook was someone he was deliberately trying to avoid as both he and Captain Hook have massive egos, and Hook was certain to double cross him if Grim didn’t double cross Hook first. Nevertheless, Hook gets dragged into the legion, with the three of them working together to locate Colossus's legendary treasure hidden on Colossus Island. Their main objective is to find three keys, The Crystal Key, The Golden Key, and The Iron Key. The villain's pursue Captain Jake and manage to steal the keys he and his crew have found. During this chase Grim makes a deal with Hook, promising him half of Colossus's treasure, knowing perfectly well he won’t hold up the bargain he made with Hook if he doesn’t have to, since who else could possibly deserve the treasure of the weakened Colossus except for him. Hook later as expected, becomes Grim's downfall, as Jake convinces Hook to help him instead, knowing that Grim was merely using Hook and had no intention of sharing Colossus's treasure with him. At the end of it, Grim, Undergear and ShiverJack are left stranded in the middle of the Never Sea on a tiny raft arguing who is the captain of the tiny vessel after being defeated. The villainous trio's anger is soon replaced by terror as Tick-Tock the Crocodile emerges out of the Never Sea and attempts to devour them. The villains flee with the crocodile in hot pursuit.

Grim has just managed to get himself away from the dreaded Tick Tock Crock, and away from his infuriated legion of pirate villains, who have lost whatever trust they previously had in him. Unfortunately, he’s now stuck on Skull Rock, trying to figure out few options he has left for revenge. After spending a full day on the haunting formation, he sees a ship coming close to the shore, belonging to a new pirate that has made their way to Neverland, looking for a stake in the competition.