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Doflamingo, you evil, evil man...
For a series known for having an idealistic hero as protagonist, it also contains some of the most monstrous and despicable actions committed by villains.
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  • Captain Kuro spent years posing as a man named Klahadore and serving as the butler to Kaya, whose father had supposedly saved his life and let him work there. Since her father passed away, he became the closest thing she had to a father figure, and the two of them did many things together. As it turns out, he was biding his time all for the day when he could kill her and claim her inheritance money, which he'd use to retire from piracy for good. The real sick part? Killing her wasn't truly necessary — he wanted to do it for peace of mind, because he'd secretly hated her all these years, finding tending to her whims to be degrading! And he tells this all right to her face when confronted about it, leading to a big Break the Cutie moment that rightfully enrages Usopp. It's no wonder he is deemed irredeemable.
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  • The World Government re-enacts the Massacre of the Innocents to find the child of Gold Roger. That and the following below, will probably earn what should be the good guys in the story a likely overthrow which is probably going to happen if the series has a happy ending.
  • "Normally, carpenters are not charged for the ships they construct, but this is in regards to the Pirate King. This is a special case. All those who supported his piracy, even a little, will be seen as dangerous."
    • Ohara's destruction for just having one person almost discovering the Void History.
    • Keeping quiet of the toxic nature of the Amber Lead in Flevance just to make more money off of the mining industry, and when a epidemic is spread they leave them to die, and slaughtering those who tried to escape. Let's face it, the higher ups have crossed the line so many times that you can write a thesis on it.
  • The World Nobles are descended from the founders of the World Government, which gives them carte blanche to treat their lessers as they see fit. They are introduced to the readers when two of them are seen sneering at a slave who was wounded after trying to escape from them, kicking him and shooting him several times. Then one of them commented how his captain collection was now ruined and tells the other that she's getting a child slave, not the giant slave she wanted next.
    • The third one was seen riding a man and kicking him the head for not going fast enough. When a doctor and a nurse were trying to get to the hospital to bring in an injured man when they should be bowing to him, the World Noble simply kicked the injured man to the ground. When he saw that the nurse was a beauty, he promptly named her his newest wife, and when her fiance stood up to him, he shot him and dragged the crying nurse away.
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    • The audience (excluding the pirates) at the slave auction were just as bad. They started laughing at Hachi and saying how thankful they were that someone had shot the monster.
  • Vice Admiral Onigumo has no problems about killing his subordinate and over a thousand other marines as long as he manages to kill the pirates.
  • Admiral Akainu, in his debut, orders the destruction of a civilian ship, all because it might just contain an escaped archaeologist. He would then show up later to execute a lowly mook who, after he saw how outclassed he was fighting with the upper class pirates and marines at Marineford, just wanted to go home and be with his family and tried to flee the battle.
  • Arlong killed Nami's adoptive mother for not having the money to pay a toll that he just imposed on the town, it looks as if he's at least willing to let Nami work to buy her town back. So he lets her join his crew and work tirelessly for 8 years to earn the 100 million berries that she needs to meet his price by going out and robbing pirates on the side. And then, when she only has one voyage's worth of money left to earn, he sends a corrupt Naval officer to steal all of the money she worked for eight years to collect. And when she confronts him about it, he has the gall to simply smile at her and ask "What promise did I break?". And then? He laughs right in her face. He later reveals that he had no intention of letting her go, and would only do so after she had drawn the map for the whole world. And considering his hatred of humans, if Luffy hadn't done anything, Nami would be let free of her association to the Arlong Pirates.
    • This becomes apparent with Hody Jones, a member of the Big Bad Duumvirate in the Fishman Island arc and Arlong's would-be successor. He's an even bigger racist and more merciless fisherman than Arlong ever was. He has the queen promoting peace killed and frames a human in order to cover his tracks. He planned to make a Fascist state out of his home country in order to spread these racist ideals and frequently uses his crew as meat shields (Where Arlong's love for his fellow Fishmen was his one redeeming quality). Because Hody despises humans and Fishmen who have compassion for them, after he takes over the kingdom and has King Neptune hostage, he decides to start killing all those who signed the peace petition that Queen Otohime had worked for. Judging from her success, he's willing to kill thousands. Finally, he has NO reason for doing this other than blind racism.
    • Vander Decken IX, the other half of Fishman Island's Big Bad Duumvirate, willingly partnered with Hody to overthrow Fishman Island's monarchy, with the side benefit of getting Shirahoshi for himself... and when Hachi (a former ally of Arlong, who Hody held in high regard) tried to persuade them to call off their plans, what was Decken's response? He used his Devil Fruit ability to impale Hachi with arrows to the point of near-death. Oh, and his willingness to flatten Fishman Island with a big frickin' boat just because he's a Stalker with a Crush and Shirahoshi rejected him.
  • Following the Paramount War, a flashback shows this to be true for practically the entire city of Goa. They arrange a pirate crew to burn down the massive junkyard next to the city and everyone living in it, as the sight of refuse and poverty could offend some visiting Celestial Dragons. If this wasn't enough, they also trap the pirate crew in the firestorm outside the city walls, so they don't have to award them the noble titles they promised. They talk about all this as if it were a pleasant spring cleaning.
  • For the longest time, even after it was revealed they ordered Ohara burned to the ground, some fans were willing to give the Five Elder Stars a pass. After all, they were trying to protect the world from ancient weapons of mass destruction. Then came the ending of the Paramount War, in which they order the escape of many vicious criminals from Impel Down covered up, and it became apparent that they're more concerned with their own power and image than protecting the world. This one was so bad that Sengoku and Garp resigned on the spot rather than work for a government that would condone such things.
  • In the Punk Hazard arc seem to show Caesar Clown gleefully doing his latest heinous actions. That subordinate of yours that sang praises of you helping prisoners/ex-pirates like him? Kill him, he's just getting in the way. Those giant children found in your labs? Hey, turns out you've drugged them (in the form of candy) to make sure that they don't leave their island. Also, their addiction to said drug causes them to go berserk when they don't have access to it. Then there's the fact they weren't giant when he first kidnapped them. And oh golly, it turns out that if they keep on using them, they'll end up dying in 5 years and he wouldn't bat an eye.
    • He's also been developing horrific chemical nuclear level bombs on Punk Hazard, which he's planning on selling to the highest bidder. One of which he's going to test by deploying on Punk Hazard, murdering everyone who isn't in his HQ.
    • What Caesar does to Brownbeard is horrible. He admits to causing the explosion that ruined his crew, while making it seem that the latter was acting crazy and pretending to be the good guy, causing his crew to turn against him.
    • Once he is cornered, he uses the powers of his Gas-Gas Fruit to merge with the poisonous gas to invoke a One-Winged Angel, and demonstrates it by killing his own minions who still have faith in him.
    • Even after Luffy defeats him, he crosses even further than he already has. Seeing that he is unable to move and likely to die, he tries to kill Smoker, via having his heart in his possession through Law's tradeoff, while the latter is completely unaware. Fortunately for the intended victim, Law anticipated that Caesar would pull something like this and actually gave Caesar his secretary Monet's heart instead.
  • Crocodile disgraced the reputation of both the Seven Warlords of the Sea (whom he was a part of) and, partially, the World Government (whom said Warlords worked for) by creating the Baroque Works crime organization and invading the kingdom of Arabasta, one of the few kingdoms uninvolved in the pirate/World Government conflict (formerly) for kicks, and to get his one greedy hand on a legendary superweapon, Pluton; along the way, he kills some of Arabasta's most loyal soldiers, and actually manages to defeat Luffy in combat. For this Troper, Crocodile crossed the line when, after it was revealed that he had hidden a bomb in the city that would reduce it to a crater, despite becoming its new ruler at the time, and the heroes manage to find it, it is discovered that it is a time bomb right near the end of its timer, meaning he had anticipated that they would find it and made sure they would still explode even if they found it. The fact that the ones who found the bomb (the princess being one of them) went down on their knees in despair and shouted to the heavens what a monster he is should say it all. Oh and he kept on sending sand storms to Toto's village, and during his first bout with Luffy, he sends a massive sand tornado to finish him because Toto was being optimistic and Crocodile felt like punishing him.
    • To put it in perspective, the next time Crocodile meets Luffy, in Impel Down, even though he acts "slightly" civil towards his old enemy, Cloudcuckoolander Luffy just looks at him in quiet disgust and, knowing better than to trust him, outright refuses to let him out of his jail cell, only doing so when he was out of any other options (he was trying to escape with his brother Ace).
  • Donquixote Doflamingo always seemed to be a nasty character, but revelations during the Punk Hazard and Dressrosa arcs that he does have genuine shared loyalty with his crew had redeemed him to an extent. Then we learned that during his takeover of the Riku Kingdom, not only he blackmailed King Riku into giving him the wealth of the entire nation, but it was actually a ruse to literally manipulate the King with his String-String Fruit into slaughtering his own people, intending to portraying himself as their savior. Even In-Universe, learning the full truth of this even has Nico Robin, a character whose pragmatism would normally have her advise against fighting someone like Doflamingo, declare This Is Unforgivable!.
  • Byrrndi World from "3D2Y" has lost sight of the person he used to be, sees his subordinates as expendable, kills anyone who disobeys him or tries to leave, and plans on using his ship's enormous cannon, originally intended as a deterrent against anyone who would come to fight him, to destroy Mariejois. But what really puts him over the line is trying to kill his sickly older brother and Morality Pet when he tries to get him to see the error of his ways.
  • Z was trying to have the entire second half of the Grand Line explode into a fiery wasteland, killing thousands of civilians and marines in the process. Even Fleet Admiral Akainu thought he must be stopped at all costs.
  • Vinsmoke Sanji's brother, Niji, crossed it when he brutally beat Cosette, an innocent chef, into unconsciousness, just because Sanji defended her cooking. All three of Sanji's brothers crossed it with their downright monstrous abuse of Sanji in the past. At the same time, it should be noted that all of their evil can also be directly attributed to their "father" Vinsmoke Judge's actions, since he literally experimented on them in the womb to turn them into emotionless TykeBombs, making them almost literally incapable of understanding that what they're doing is wrong. Considering how Reiju and Sanji turned out otherwise...
  • Vinsmoke Judge was a complete asshole from his very first apparition. He was shown as an even bigger asshole as he was revealed to be Sanji's Archnemesis Dad, plus the horrible circumstances that led to this and how he only wants Sanji back to force him in an Arranged Marriage. But what made all of this worse was The Reveal that he experimented with Sanji and his quadruplet brothers (Ichiji, Niji and Yonji) when the four were still in their mother Sora's womb, intending to make them Tykebomb super soldiers with zero empathy from before they were born. The reason why he hates Sanji so much is that, thanks to a risky gambit from Sora, he was the only one who escaped to this.
  • Kurozumi Orochi crossed it when he mixed SMILEs that failed to produce Gifters into the usually rotten leftovers sent to the impoverished Ebisu Town, knowingly tricking the inhabitants into becoming Pleasures incapable of expressing emotions like grief due to being unable to turn away actual fresh food. Why? The twofold reason of both being tired of them constantly mourning their dead and out of pure unadulterated spite towards the former Daimyo, Yasuie.
  • Daifugo/Scorpion, the vicious warden of Udon Prison, crosses this when he starts murdering Udon's prisoners completely at random with bullets filled with the "Mummy Virus", until the infection spreads to Luffy and his allies. Said virus inflicts unbearable pain on its victims, as if their entire bodies are on fire, as Daifugo himself sadistically explains.
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