Magnificent Bastard / Darker than Black

November 11: After you bring me a little acquisition and I ensure there's been no mistake, you'll receive two more briefcases of cash just like this.
Mob boss: And what do you plan to do with this acquisition, Mr. Smith?
November 11: Well, to start, I thought I'd walk through the doors of a rival company and kill 3000 of their best men! Kidding. Actually, I'll just resell it.

— "Red Giant Over Eastern Europe"

The world of Darker than Black runs on Black-and-Gray Morality where people give up their consciences to become supernaturally-empowered Contractors. Amidst the Gambit Pileup set up by the diabolical Syndicate and its rival organizations, as well as their more self-interested underlings, some schemers mark themselves as truly remarkable.

All spoilers are unmarked. You Have Been Warned!

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Series-Wide

• Hei began life as a young boy watching the stars with his sister Bai before the appearance of the Gates. Becoming an assassin to look after Bai, Hei became known and feared as the "Black Reaper" for his prowess in killing Contractors with strategy and skill. After Heaven's War, Hei becomes an agent for the Syndicate where he regularly kills Contractors with almost impossibly brilliant gambits, beginning the series by utilizing a brainwashed Doll to get close to his targets while acting as a careless fool in his civilian identity of "Li Shengshun" before slaughtering his enemies. Hei later dispatches another expert assassin by using his powers to restart his own stopped heart and resorts to splashing himself with his own blood to fool an enemy Contractor whose own blood is a deadly weapon, then ambushing and effortlessly dispatching him. Hei is constantly able to fool even his own handlers, friends and enemies alike, at one point assisting a young man saving a Doll bound for the sex trade while never revealing his true identity. Finally turning on the Syndicate, Hei is able to take a third option in the choice between the destruction of Tokyo and the Contractor race, saving the planet several times after. Even after losing his powers, Hei displays the same trademark skill in overcoming his enemies and remains one of the most feared men alive.

The Black Contractor

• Amber is an elusive, mysterious woman who betrayed MI6 to work for the Syndicate, eventually leading the deadliest squad of Contractors in Heaven's War. Realizing the Syndicate's true intentions and using her powers to see and rewind the future countless times, Amber manipulated the Syndicate and her own side to seal off Heaven's Gate, which caused a massive disaster that rendered most of South America uninhabitable. Returning in modern day Japan leading her own organization of Contractors, Evening Primrose, Amber orchestrates a series of bombings while kidnapping the scientist behind the Saturn Ring project, manipulating her former lover Hei and the world's intelligence agencies to place Hei close to Hell's Gate so he can seal it as well and prevent the Saturn Ring project from killing all the world's Contractors. After settling things with Hei, Amber sacrifices herself to rewind time and give him a chance to choose a third option, later revealing she had foreseen that possibility and left guidance in the new world Hei had made.
• November 11, alias Jack Simon, is a suave Contractor and one of MI6's best agents. First seen recovering the inactive former war criminal Havoc, skillfully reversing a double cross and eliminating everyone after interrogation, November later kills Havoc before she can reawaken to her Contractor state, showing himself the equal of Hei himself with a plan to nullify his electric currents. Later learning of the Syndicate's true reach and schemes, November defects to Evening Primrose and leaves his close ally Misaki Kirihara with clues she needs to dismantle the scheme, sacrificing his life to kill his former superior Decade in a choice his partner April describes as a rational decision and end that any Contractor would be proud of.
• "When One Takes Back What Was Lost Within the Wall" two-parter: Nick Hillman masquerades as a PANDORA research assistant who longs to gaze upon the stars of the old sky. In truth a Contractor desperately trying to reunite with his sister, Nick skillfully manipulates and murders within the facility as needed, even wiping out his own reconnaissance team to obtain a Reality Warping object from beyond Hell's Gate. Nearly managing to kill Hei himself, Nick ultimately reunites with his sister in a dreamlike world reverting to a child, leaving the Earth behind with her as a spaceship carries them to the stars.
• "A Heart Unswaying on the Water's Surface" two-parter: Bertha and Itzhak are a pair of Russian Syndicate Contractors assigned to hunt down the Doll Yin. Remarkably introspective for their kind, the duo also operate seamlessly, with Bertha using her vocal powers to incapacitate a police officer hunting for them and Itzhak his own ability to draw in observance spectres to blind their enemies. Nearly killing Hei himself to accomplish their mission, even when fatally wounded they just melancholically muse on the nature of being as they die.
• "Dreaming Shallow, Uninebriated" two-parter:
  • Shihoko Kashida is a Contractor with the power to rupture human organs the price for which she pays is to temporarily regain her emotions. Having seduced Huang, Shihoko fell in love with him for real and murdered his partner in front of him for her mission and partially to protect Huang. Assigned to kill the cult leader Contractor Alma, Shihoko spends three years fooling the cult deep undercover until being found by Huang and Hei. Revealing the truth of her emotions to Huang, Shihoko realizes he will be hunted as long as she lives and ends up using her death in such a way to spare him.
  • Alma is the charismatic founder of the "Fraternal Order of the Holy Gate" cult, who seeks to create a world of equality between humans and Contractors. With her ability to change her appearance, Alma inspires her followers with her words and murders any Syndicate operatives sent after her. Managing to persuade Hei himself to look beyond the Syndicate's schemes, Alma ultimately shatters his faith in his self-interested employer.

Gemini of the Meteor

• Shion Pavlichenko is a driven, unscrupulous Contractor who creates an Opposite-Sex Clone of himself to replace his dead twin sister Suou. Creating a clone of his father to be killed in his place for he and Shion to escape an attack to plot from behind the scenes, Shion manipulates events to have "Suou" venture to meet him at Hell's Gate, even murdering Suou's former friend and forcing her to be rejected by her horrified mother along the way. Using Hell's Gate's power to amplify his cloning ability, Shion uses all his strength to create a happy world for Suou, dying feeling fulfilled.
• Madame Oreille is an elusive French agent with a wealth of knowledge on everyone she deems useful for her mission. Targeting key persons for her own ends, Oreille uses a combination of choice words and giving information she knows will peak their interests, swiftly turning them into assets for her plot. Revealed to be helping Shio realize his dream and save the records of all of mankind's memories, Oreille operates meticulously to see her goal through.