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* ''[[Sword Art Online]]'' designer Akihiko Kayaba, a pioneer in the field of Virtual Reality (VR), traps 10,000 players inside his game, killing them in the real world if they die in the VR one. Disguising himself as [[Big Good]] Heathcliff and guiding the players through the dungeon floors of Aincrad, Kayaba intends to betray and kill them in the last dungeon, acting as the [[Final Boss]] of his own game. When Kirito is able to deduce "Heathcliff's" true identity, Kayaba praises the boy for his observance before challenging him to a duel, promising to end the game of Kirito wins. Keeping his word and freeing the players, Kayaba seemingly commits suicide, though actually copying his Fluctlight onto the internet to continue existing. Reappearing in the next arc, Kayaba helps Kirito defeat the [[Arc Villain]], Sugou, whom even he finds repellent. Entrusting Kirito with his last invention, Kayaba encourages him to go on to share it with the world, leading to the creation of many innovative VR games. Though utterly sociopathic, Kayaba never strayed from his strict moral code and stood out as one of Kirito's most noble foes.
** Initially presented as Kirito's eccentric and annoying benefactor, Seijirou Kikuoka [[Beware the Silly Ones|is revealed to be much more]]. Actually a lieutenant in the JSDF, he leads RATH, creators of the virtual world Underworld, which is inhabited by highly developed AIs known as "Artificial Fluctlights". Convincing Kirito to work in the Project Alicization while hiding its morally dubious aspects from him, Kikuoka intends to use "complete Fluctlights" as combatants, hoping to avoid human casualties in warfare and showing Japan's potential to the world. After Kirito is hospitalized and suffers from brain damage, Kikuoka takes him from the hospital to the Ocean Turtle and connects him to the Underworld, hoping to save his mind out of genuine concern and affection. After the Ocean Turtle is attacked by Glowgen Defense Systems, Kikuoka helps to defend it, sends Asuna to the Underworld to save Kirito and stop the sociopathic Gabriel Miller, and is injured while trying to protect his companions. Initially willing to sacrifice infinite AIs for one single human, Kikuoka learns to value the Underworld and promises to protect it. Having helped Kirito and Asuna one last time, he successfully fakes his death after showing Japan's potential, [[Karma Houdini|completely avoiding any punishment.]]
* The
* [[Black Knight|AxeKnightmon]] of ''[[Digimon Xros Wars|Digimon Fusion]]'', whose magnificence is aided by being as [[Badass]] as [[Black Knight|his name]] would suggest. {{spoiler|1=He spends years manipulating a meek [[Child Prodigy]] into thinking that the Digital World is a game where no one can die so that he'll willingly work for him and grant him access to [[Fusion Dance|DigiXros]], then blackmails his sister into helping him too by using him as a hostage, neither aware of the other's true situation. While he is a servant (and younger brother) of the [[Big Bad]], Bagramon, he poses as the leader of [[Evil Versus Evil|a rival faction]] for much of the series, and even spies on and sabotages the plans of the [[Quirky Miniboss Squad]] (partly to keep up the charade, partly [[Enemy Civil War|to make himself look better]], but mostly because [[For the Lulz|it's hilarious]]). And in the end it turns out he really ''was'' [[The Starscream|working against Bagramon]] - he [[Stealth Mentor|encouraged the protagonists to get stronger]] so that they would be around to attack Bagramon while he was focusing most of his power into his doomsday technique, allowing AxeKnightmon to stab him in the back while he's distracted and absorb him.}}
** The manga's version of Bagramon also qualifies. Rebelling against Homeostasis because of her plan to have Digimon branded as heroic or villainous, in a system that would result in his brother's death, Bagramon is defeated and exiled. Finding the remains of the digital deity Ygdrassil, Bagramon uses them to empower himself and begin his conquest, creating the Xros Loader and the powerful artificial Digimon Tactimon. He then rebels again with the loyalty of dark Digimons, defeating the Royal Knights and breaking the digital world. Manipulating his brother using two minions and some humans, Bragramon intends to judge humans and Digimons based on who wins between them. When his brother "wins" while losing his sanity, Bagramon cries for him before using him to recreate Zeed Milleniunmon, intending to use it to euthanize both the digital and human worlds and save them from decay. When he is proven wrong by the heroes, Bagramon cheers for them and dies saving his brother, encouraging him to be better.
** Devimon and Myotismon from
** There was also {{spoiler|Yukio Oikawa}} from ''[[Digimon Adventure 02]]''. The guy was pretty much behind everything that happened in the series, and he started it all with just {{spoiler|a simple e-mail he sent to Ken Ichijouji, a young boy wretched with guilt over his brother's death that he blamed himself for, which tells him to use the digivice he found some time ago to travel into another world. Little Ken does so and ends up in the Dark Ocean, a world of darkness and negativity which corrupts Ken into the evil Digimon Emperor. Now with Ken as his unknowing pawn, he uses him to conquer the Digital World and set up Control Spires, obelisk towers of darkness used to weaken the Digital World's defences and, in the long term, the border between the Digital World and the Real World. However, when the Digidestined defeats Ken and cleans the Digital World of the spires, Oikawa sends his agents Arukenimon and Mummymon to kill them by transforming the spires into monsters, and to destroy the Destiny Stones in order to hasten the weakening of the border. With enough Destiny Stones destroyed, the border becomes so weak that Digimon invade the Real World in thousends, and with that as a convient diversion, Oikawa moves on to his next step. He and his minions recruits some lonely kids with promises of power and talents and then kidnaps Ken, copies the Dark Spore that was planted inside him, and transplats the copies inside the children. With time, those copies would grow into something so powerful that it would give Oikawa the final crack on the border he needed to enter the Digital World and claim it as his own. A simple goal which required complicated tactics and difficult planning to reach, and yet Oikawa pulled it all off like it was no problem at all. But then it's revealed that he was just a pawn of Myotismon all along, and that Myotismon is the true [[Chessmaster]] of ''Adventure 02''}}.▼
▲** Devimon and Myotismon from the original ''[[Digimon Adventure]]'' could be the first ever contenders for this trope in the franchise.
*** Devimon, as the first ever [[Big Bad]], was behind all Black Gears and traps set for the children on File Island and rarely lost his composure, even while dying! Not to mention that he was probably the only Digimon villain who had some sanity in him, except the conquest thing. Even in death, he still pulls some strings behind the scene; by appearing before the Digimon Emperor he played on Ken's superiority complex into making him use some of his own data to create Kimeramon and so, Devimon had full control of it and gladly use Kimeramon against the Digidestined and the emperor.
*** Meanwhile, Myotismon's entire scheme for traveling to the Real World is a gambit to kill the Eighth Child before she can fulfill her destiny and defeat him. He distributes mock crests to his minions so that they can tell when they're near the chosen child, and when that fails, he uses that child's potential partner to pick out the child for him (all while keeping the digivice and crest safely far away). He is charming enough to beguile human women so he can drink their blood in a weirdly sexual way, and his plans are shrewd enough to be frighteningly competent. And this is just the first season!
** In the second movie, "Our War Game", Diaboromon's mad search and hunger for data earns the attention of Gennai and the DigiDestined. Assaulted as a Keraman by Tai, Izzy, and their Digimon, he tricks the latter two by jumping from Rookie to his Ultimate Form, Infermon, and subsequently overpowers them. Earning his first victory by attacking them mid-transformation, Infermon escapes and covers his tracks by clogging up the dial-up phone lines. When Izzy uses a satellite uplink to continue the pursuit, Diaboromon hijacks the connection to send missiles to Colorado and Japan to put them on the clock. Multiplying himself to hide the real one to kill time, it takes the might of Omnimon to destroy them all. Although Diaboromon resorts to outspeeding them, he's eventually caught and defeated. Returning in the sequel, he orchestrates his revival by tricking the DigiDestined into opening gates for his Kuramon swarms. Diaboromon holds out against his old foe Omnimon in the Digital World, showing how much he learned, before successfully digivolving into Armageddemon in the real world. Boasting a mere two appearances, Diaboromon regardless managed to be one of the DigiDestined's most cunning, adaptable, and dangerous adversaries.
▲** There was also {{spoiler|Yukio Oikawa}} from ''[[Digimon Adventure 02]]''. The guy was pretty much behind everything that happened in the series, and he started it all with just {{spoiler|a simple e-mail he sent to Ken Ichijouji, a young boy wretched with guilt over his brother's death that he blamed himself for, which tells him to use the digivice he found some time ago to travel into another world. Little Ken does so and ends up in the Dark Ocean, a world of darkness and negativity which corrupts Ken into the evil Digimon Emperor. Now with Ken as his unknowing pawn, he uses him to conquer the Digital World and set up Control Spires, obelisk towers of darkness used to weaken the Digital World's defences and, in the long term, the border between the Digital World and the Real World. However, when the Digidestined defeats Ken and cleans the Digital World of the spires, Oikawa sends his agents Arukenimon and Mummymon to kill them by transforming the spires into monsters, and to destroy the Destiny Stones in order to hasten the weakening of the border. With enough Destiny Stones destroyed, the border becomes so weak that Digimon invade the Real World in thousends, and with that as a convient diversion, Oikawa moves on to his next step. He and his minions recruits some lonely kids with promises of power and talents and then kidnaps Ken, copies the Dark Spore that was planted inside him, and transplats the copies inside the children. With time, those copies would grow into something so powerful that it would give Oikawa the final crack on the border he needed to enter the Digital World and claim it as his own. A simple goal which required complicated tactics and difficult planning to reach, and yet Oikawa pulled it all off like it was no problem at all. But then it's revealed that he was just a pawn of Myotismon all along, and that Myotismon is the true [[Chessmaster]] of ''Adventure 02''}}.
** [[Digimon|The franchise's]] greatest example would be Millenniummon, since unlike all the others he ultimately achieved what it wanted
* ''[[Lone Wolf and Cub]]'': Both the protagonist and antagonist are viciously efficient operators:
** Series [[Anti-Hero]] Ogami Itto is a stoic, charismatic warrior unjustly framed by the Yagyu clan. On the run with his three year old son Daigoro, Itto constantly showcases his strategic genius in his assassinations. In one instance, he allows himself to be captured by the enemy to get close to a target, revealing that the warning they received was written by him. In another, he uses Daigoro drowning as bait to trick a target's bodyguard into trying to save him so Itto can kill him. Itto singlehandedly brings down the powerful Yagyu clan on his own, showing why he is a man who walks the road of demons, the Path of Meifumado.
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