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Start of Darkness
We first see Redcloak (who at this point has no such title) 34 years before the main comic takes place living amongst a small society of goblins. The goblins are suddenly invaded by a small force of elite Sapphire Guard paladins. Nearly all the goblins are slaughtered, including Redcloak's mentor, the bearer of the Crimson Mantle. As his friends and family are murdered around him, Redcloak sees a vision of the spirit of his former mentor, who instructs him to don the Crimson Mantle. Redcloak obliges warily, and as he does, suddenly learns all the secrets of the goblin deity, The Dark One. Thanks to his new found power, Redcloak escapes the paladins, and he saves his little brother, who has had one eye sliced out by one of the paladins. The two are the only ones to survive the massacre.
Four years later, Redcloak and a small army of goblin warriors are preparing to lay seige to an Azurite fort. Just before they launch their attack, they are interrupted by a group of lizardfolk who begin killing the humans. Redcloak and his brother's attention is then diverted to Xykon, who is flying up above. They see him start slinging destructive spells at humans and lizardfolk alike. The two goblins manage to negotiate an alliance with Xykon, and receive the name they will be known as for the rest of the comic: Redcloak and Right-Eye.
Redcloak and Right-Eye take Xykon to an evil diner, where Redcloak reveals a plan to take over the world. He seeks control of The Snarl, a god-killing abomination locked inside the planet. He needs Xykon to do the ritual which will unlock the gate holding The Snarl in its prison, and then he can use The Snarl as a weapon to create an equal world where low-level humanoids receive the same privilages as the humans, elves, dwarves and halflings.
The threesome and their goblin batallion enact this plan three years later. The gate is within Lirian's Glade, and guardded by a large group of elves and forest creatures. Though the goblin army originally has the upper hand, they are defeated by Lirian's 'Guardian Virus', which removes the magic from the goblin spellcasters, and most importantly Xykon, whose unequaled power is lost, reducing him to a feeble old man. He and the goblins are captured and locked in an underground prison from which they seemingly can't escape. However, due to the Crimson Mantle, Redcloak is unaffected by the Guardian Virus. He conducts a ritual to transform Xykon into a lich. As an undead, Xykon is no longer affected by the virus, and retains all his former power. He blasts the goblins out of their prison. Redcloak goes straight away to seize the gate, but accidentally destroys it in a forest fire. He believes all is lost, but is wrong - for Xykon has just obtained the knowledge that Lirian's Gate is jsut one of five gates dotted across the world, so they have more chances to gain power over The Snarl.
After becoming tiresome of Xykon's unrelenting evil, Right-Eye leaves 'Team Evil' to start a family in a small goblin village. Redcloak does not join him until eighteen years later, after Xykon goes missing. Still keen to carry out 'The Plan', Redclaok has his eyes on a mysterious monster who resides in the shadows. He is childlike in nature, but Redcloak knows him to be extremely powerful. One night Redcloak, assisted by his nephew Ridiziak, breaks the Monster in the Darkness out of the circus he belongs to. After the mission is successful, Xykon arrives in the goblin settlement. He orders everyone out their homes to join his army. Redcloak, Right-Eye and his family reluctantly accept.
Redcloak's final scene in Start of Darkness is set some six months before the start of the comic. Xykon, Redcloak and Right-Eye are trying to coax the mage Dorukan out of his castle, the location of the next gate. Right-Eye now hates Xykon passionately, after he watched and laughed as adventurers killed his family. As Xykon and Dorukan engage in a duel, Right-Eye flies up to kill the lich. Torn, Redcloakultimately decides to kill his own brother, believing it to be for the good of the goblin people. When queried about Right-Eye's death, he lies to Xykon, telling him that he fell while flying up to help him. He refuses to animate his brother as a zombie. Xykon knows the truth, and delivers Redcloak a speech on how he will never be able to accept the truth, and thus Xykon will always have power over him. Redcloak grudgingly accepts this as Team Evil takes Dorukan's castle.
Dungeon Crawlin' Fools
When The Order of the Stick reach the bottom of the Dungeon of Dorukan, the team leader Roy throws Xykon into the gate, blowing him into pieces. The Order is unaware that he actually still lives in the phylactery Redcloak wears round his neck. As they leave, Elan destroys the gate and the castle in the process.
No Cure for the Paladin Blues
Redcloak and Xykon travel to a library in tower containing a book with the locations of the rest of the gates. By a mad turn of events, Redcloak ends up Supreme Leader of tens of thousands of hobgoblins. He leads the march to the next gate - in Azure City.
War and XPs
The invading army plan to use the advantage of surprise on Azure City, systematically destroying each of the early warning beacons so as not to alert the city on their imminent attack. Their plan changes when they encounter Miko Miyazaki, a Sapphire Guard paladin, who they decide they can use as an asset to scry on and find out the location of the next gate within Azure City. This is successful, and they discover the gate is concealed in a sapphire located on the top of the throne.
The siege begins with Redcloak's order to fire the catapult. He launches several Titanium elementals which smash against the wall that surrounds Azure City, instantly weakening their defenses. The hobgoblin hordes swiftly move inwards. In order to confuse the paladins and protect Xykon, Redcloak has created three Xykon decoys. The defenders soon realise, however, that the real Xykon is invisible and flying above them atop a zombie dragon. Roy leaps on to challenge him, but is killed in the process. Xykon moves on to the throne room.
Back at ground level, Redcloak is watching the battle unfold and making plans. He has no sympathy for his hobgoblin minions as he sends thousands of them to their death. After a hobgoblin saves his life, he realises how unjust his xenophobia is, and charges into battle riding a giant red mammoth. He is able to surpass Azurite fortifications and enters the castle courtyard, where he kills the High Priest of the Twelve Gods. He also first encounters Tsukiko, a mystic theurge who had been hired by Xykon as the newest member of Team Evil not long earlier. He takes an immediate dislike to her, in part due to the fact that he has an inherent hatred for all humans.
Recloak finds Xykon in the castle throne room where he is fighting off a small army of paladin ghosts, among them Soon Kim, the creator of the gate. The two fight well, but are not powerful enough. They seem to be defeated when Miko enters the room. Deluded, she destroys the gate, blowing up the castle and giving the goblin and the lich a chance to escape.
Don't Split The Party
After Xykon and Redcloak successfully win the war for the hobgoblins, he persuades his boss to remain in the now occupied Azure City (though he wished to move on to another gate), as the other two gates were likely to be heavily defended, planning to create a new city for his people.
To help convince Xykon to allow him to do what he wished, Redcloak convinced him that O-Chul was withholding information from them regarding the other gates, and Xykon allowed him to interrogate him, though the lich deliberately endangered his life for his own amusement while he was not doing so.
This would later lead to Xykon temporarily losing his phylactery, after Vaarsuvius teleported to Azure City to slay him. During the chaos, O-Chul managed to escape, and pierced his eye using one of the bars of his cell, nearly killing him and taking the phylactery for him in the process.
The phylactery nearly fell into the Snarl's rift, though it ultimately fell into the sewers. Xykon, furious at Redcloak's incompetence, forbade him from regenerating his eye, causing him to resemble his brother. Aware of the similarities, he began to mock the bearer of the Crimson Mantle for the choices he had made, referring to him as Wrong-Eye or Red-Eye.
Afterwards, Redcloak renamed Azure City Gobbotopia, and promoted Jirix to Prime Minister of the city.
Blood Runs In The Family
Realizing that the resistance are also searching for the phylactery so that they can find a way to destroy Xykon, Redcloak plants a spy inside the organization, who alerts him where he can find their hideout. He proceeds to take action against them.
Redcloak wipes out the majority of the resistance by summoning several devils along with an Osmium Elemental to assist him in this grisly task. After the few remaining members (who were on a mission to retrieve the phylactery, which they succeeded in) return to the base, Redcloak and his summoned minions make quick work of them, with the hobgoblin spy tricking the resistance member carrying the phylactery into heading into a secret tunnel containing a pit fiend, then delivering it to his master after she is torn in half.
Thanh slays the resistance spy for betraying the resistance, but he is grabbed by Redcloak's Osmium Elemental. He tries to persuade the high goblin priest without his summoned minions by asking him if he was afraid to face him, but he tells the paladin that he did not wish to take any unnecessary risks, and ordered the Osmium Elemental to crush him to death. Only one of the resistance members survived to alert Hinjo of the group's destruction.
Shortly afterwards, Tsukiko confronts him when she notices that the scroll they are using for the ritual seemingly does not allow one to control the Snarl and was in fact designed to teleport it. She alerts Redcloak that she is going to tell Xykon about her suspicions, believing that he would allow her to do whatever she wanted and that Xykon would make her his new second-in-command.
Redcloak's response is to take control of her wights, order her to grapple her (which would prevent her from using almost all of her spells), and ward his study to prevent her from teleporting away. Berating Tsukiko for her foolishness, Redcloak instructed her wights to drain the life from her, then devour her corpse to dispose of the body and to prevent her from being resurrected. Likewise, he also instructed the wights to devour themselves in the order their mistress created them, and for the last one to incinerate themselves in his fireplace.
He explained what he had done to Xykon, using careful wording to make it sound like Tsukiko was planning to betray him. After forging a fake phylactery with the help of a hobgoblin, he hands it to his master and proceeds to guard it using powerful magic in an alternate dimension.
Afterwards, he arrives at Girard's Pyramid, just in time for it to explode and significantly injure them. Redcloak tries to persuade Xykon that the Order Of The Stick are a threat to him and that they must be wiped out, but after the Monster In The Darkness bluffs Xykon into believing that O-Chul was a bigger threat to him and that he was on his way to Kraagor's Gate, he believes that Redcloak is trying to set up a goblin colony in the desert like he did with Azure City and demands that they leave. The goblin reluctantly obeys, though not before summoning a Silicon Elemental to slay the Order Of The Stick, starting with Roy Greenhilt.