Magnificent Bastard/Anime/One Piece

The most magnificently roguish and scheming scoundrels who sail the seas of One Piece.


 * The guy who kicked the series off to begin with, Gold Roger, is easily one of the biggest examples in the series. As one of history's greatest pirates, he and his crew blazed a trail around the world, pulling off all sorts of crazy heists and schemes, touching the lives of the many friends he'd make, defeating all who would oppose him, and ultimately doing the unthinkable: conquering the treacherous Grand Line and finding the fabled island of Laugh Tale. And upon learning he was dying from an incurable disease, Roger did everything he could to usher in a bold new age of piracy by uncovering forbidden knowledge of the world and making sure it could be passed down to those who sought it out, leaving all the treasure he gathered on Laugh Tale as the One Piece, and allowing the World Government to publicly execute him so he could kick-start the mother of all treasure hunts with his last words before dying with a defiant grin on his face. And keep in mind, he did all of this without a Devil Fruit!
 * Sir Crocodile, AKA Mr. 0. This guy manipulated an entire kingdom into a civil war between the king and his people while still presenting himself as a hero to the country. His entire slogan for his plan was, "The love for this kingdom will destroy it." He also added even more insult to the heroes about telling them about a bomb that would blow up the town square that was nearly impossible to stop because he had a backup in case his lackeys failed to set off the bomb. His plan was nearly flawless and would had succeeded if it was not for certain events.
 * In a side-story that took place after his defeat, Crocodile took over his jail block and, when given a perfect chance to escape, chose to light up a cigar and stay put. He would later agree to an Enemy Mine to break out of The Alcatraz that is Impel Down solely for the chance to kill an old enemy (who, incidentally, everyone else wanted to help save).
 * His successor in the Seven Warlords of the Sea, Blackbeard, is perhaps even moreso. The current part of his Gambit Roulette slash Batman Gambit resulted the biggest battle/war in the history of it's world, and manipulated all sides involved effortlessly, and got exactly what he wanted from it: . And he got away scot free, and because of the WG's pride, won't even be hunted down by them. All for his plan to become Pirate King.
 * Vice Admiral Jonathan of the G-8 "Navarone" facility is a rare semi-heroic example. The Straw Hat pirates just happen to fall directly into the impenetrable fortress at the same time that an inspector with an ulterior motive to have the place shut down pulls in. Rather than trying to deny the event, he takes time and makes observations about the crew, even when they show in front of his very face, turning their quirks to support a morale boost of the base's personnel and discredit the obstructive inspector. It's important to remember that his primary goal is to maintain the Marines' support of the facility, not the capture of the pirate crew, and even when things don't follow his voiced plan, he still comes out ahead.
 * Donquixote Doflamingo also made a gambit of taking over a country, and succeeded in a day and a night. He managed to keep power for a decade. His grip of the country was only shaken because of a single blunder by one of his subordinates, whose powers made everyone else forget about the very existence of the person who eventually led the resistance. Before that, he managed to position himself so well even his enemies (the World Government) were forced to cooperate. He also set himself up with one of the Four Emperors, Kaido, ensuring that anyone who went after him also risked the intervention of the Emperor. Even though he isn't as powerful as the admirals or the Emperors, he expertly maneuvered his way to the top. Only Luffy and Law are crazy enough/have enough knowledge to hit him where it hurts.
 * Trafalgar Law, after the timeskip. He become one of the Warlords of the Sea in order to get in close on Caesar Clown in order to stop his production of the SAD, a chemical crucial in the production of artificial devil fruits, but he also used this attempt to press Donquixote Doflamingo into quitting the Warlords. He is smart enough to befriend the protagonist, forming an alliance with him to take down Kaido of the Emperors (who wanted the SAD chemical). And last, but not least: he tricked Caesar Clown into stabbing what Clown thought was Smoker's heart, while it in reality was the heart of his own second in command, Monet seconds before she would have released an attack that would have killed everyone except for Clown, which he would have been perfectly fine with. It Makes Sense in Context.
 * Law's fellow supernova Capone Bege also comes into his own after the timeskip, though he was already a notorious chessmaster before it. A sharp-dressed mafioso-turned pirate, Bege isn't a brawny bruiser like most pirates in his weight class, but a master strategist who prefers psychological warfare and defensive maneuvers with his Castle-Castle Fruit. When he and the Straw Hat Pirates team up to take down Big Mom, his assassination plot that exploits her fragile mental state nearly goes off without a hitch, only failing due to pure bad luck. And when his wife Chiffon is taken hostage during the resulting hasty escape, he does the equivalent of a hit-and-run driveby shooting to save her and spirit her away, freeing her from her abusive family while getting away with making Big Mom look like a fool. While a sadistic thug who loves to spread chaos by toppling down powerful authority figures, he's also an honorable man who keeps his promises, a husband and father who deeply loves his family, and is good at landing on his feet when his well-thought out plans go awry.
 * Buggy the Clown also qualifies, oddly enough. While not as personally powerful as the above examples, he made it across The Grand Line just fine prior to Impel Down. Once he got captured, he managed to conceal his Devil Fruit abilities while getting locked up in a supermax prison and thus avoided receiving Seastone restraints (and also managed to sneak in powerful explosives), used carefully worded lies and half-truths to talk a bunch of incredibly powerful and dangerous convicts into working for him, thereby gaining one of the strongest crews in the series, and post-Time Skip, it's shown he managed to talk his way into a cushy position as one of the Warlords, all while operating under the guise of Obfuscating Stupidity. He's essentially John Constantine in the form of a pirate clown!