Much of the drama in the anime and manga of One Piece comes as a result of everyone's different ambitions and desires, but some of it comes from the characters making bad decisions, being clueless about their own idiocy and then being punished for it.
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General/Pre-Story Events
- A bunch of people ate mystical fruit that gave them superpowers but made them unable to swim.
You'd Expect: Them to immediately take a sturdy merchant ship to the nearest continent and live out their lives in a low-moisture area.
Instead: They keep living on a string of islands, and half of them work as sailors. Admittedly, this does have some historical justification: even in the real world, pirates and sailors of the old days could not often swim.
Admittedly: The world of One Piece only has one continent — the Red Line — and both reaching it and scaling it (it's situated in the middle of some ridiculously dangerous seas and rises thousands of meters above the sea level) is considered near impossible without having a really strong crew and a ship that can travel on walls (like the immensely wealthy Vinsmoke family). The rest of the entire world is made up of nothing but scattered islands and the occasional archipelago, meaning that it's kind of hard for Devil Fruit users to avoid the water. - Zeff taught Sanji a lesson to never hit women, which explains the latter's feelings for them.
You'd Expect: For Zeff to give him an extra lesson that he is only allowed to attack women that are evil. Take Kalifa, for example.
Instead: He never thinks about doing the above, which led to the complications below when Sanji encounters Kalifa in Enies Lobby, and Black Maria in Wano. - Vice Admiral Garp wants to make sure that his grandsons, Monkey D. Luffy and Portgas D. Ace, grow up to become respectable Marines, or at the very least anything other than pirates. Unfortunately, he's unable to raise the kids himself (presumably due to his duties as a Marine).
You'd Expect: Garp to try and put Luffy and Ace in the care of people who he knows will raise the kids right. As a Vice-Admiral, and one of the most important figures in the Marines, Garp would presumably have a number of subordinates on hand who could fit this role in some way. He could also make sure they're kept away from negative influences, and work on building up a bond with them, so that he'll have more chance of influencing their decisions.
Instead: Garp just leaves Luffy and Ace in a backwater village in East Blue. Luffy subsequently befriends a crew of pirates (Garp apparently making no attempt to stop this) and decides he wants to become a pirate. At this point, Garp realizes that he made a mistake, takes Luffy out of the village... and sends him to live with a load of bandits, which naturally does absolutely nothing to curb Luffy's ambitions, or teach him respect for the law. And when Garp is around, his interactions with Luffy consist solely of him giving the kid a Hilariously Abusive Childhood, leading to Luffy fearing him more than anything.
Result: Luffy becomes one of the most notorious pirates in the world, and Garp has to deal with the very real possibility that he'll either have to fight his grandson, or watch him be killed by the World Government's forces. And this is exactly what happens to Ace during the Marineford arc.
Admittedly: Ace and Luffy are the children of the two most wanted men in the world, the deceased Pirate King Gol D. Roger and the Supreme Commander of the anti-World Government Revolutionary Army Monkey D. Dragon respectively. If they had come into Marine custody, there would have been no guarantee that the more brutal elements in the organisation like Sakazuki or operatives from another WG agency, like the Cipher Pols, would've let the boys live. - Nami's backstory has this. It's revealed that after Bellemere died, Nami cried Tears of Remorse, believing it was her fault since Bellemere, rather than save herself, said the paltry money she had would keep her two children — Nami and her sister— alive. Arlong then finds out Nami is a great navigator and cartographer; he makes a bargain with her that she'll join his crew, and if she pays a million berries, he'll set her free. Only her sister knows that she's entered indentured servitude with Arlong to make sure no one else in the village dies. When Sanji finds out and declares they need to save Nami, Nojiko says Nami doesn't want their help because she doesn't want another death on her hands.
You'd Expect: That Arlong would honor the agreement. Even if Nami is too valuable as a navigator, he has entire decades' worth of her expertise. Plus, she has nowhere to go due to the whole joining pirate crews and then stealing their money to pay the ransom. Luffy forgave her because he knows there must be more to the story, but Nami is seen as a "brat" overall. Arlong still can hire her, with a new deal.
Instead: He has a corrupt Marine take all the money just as Nami is preparing to buy her freedom and that of the villagers. Nami puts on a brave face about it and says she'll save up again, but eventually breaks down crying knowing that it means she is trapped forever or that the village will die fighting off the pirates. Arlong gives an Evil Laugh while talking with his crew that it means Nami is his servant for life.
The Result: This leads to his downfall. When Luffy sees Nami crying and begging him for help because her neighbors and friends will die in her name, he gives her his hat for safekeeping, and challenges Arlong to fight for hurting Nami's feelings. He's not happy and gives one heck of a fight. When Arlong tries to bargain with Nami to surrender, she remembers he's dishonorable and says she'd rather die fighting than trust him again. Oh, and Luffy not only destroys the map room where Nami spent her childhood but also ensures Arlong is defeated. - Right after Bellemere was killed as mentioned, the Arlong pirates see one of Nami's maps and decide that she would make a good navigator so they kidnap her and the villagers watch this helplessly. After some time Nami returns with a lot of money, the Arlong crew tatoo and a forced smile. She then confesses she joined them and that she got that money from them for drawing maps.
You'd expect: The villagers to realize that the poor traumatized girl joined the crew out of fear and that they will be gentle with her.
Instead: They are shocked Nami would do something like this and call her out for it, hurting her even further. Later Nami reveals to Nojiko that she joined the Arlong pirates in order to make enough money to pay the debt for her village, thus setting the village free. Very well thought guys. - The villagers at first are infuriated that Nami is allied with Bellemere's killer, but they find out in secret that she entered the deal to save them. They also found out from Nojiko that Nami feels guilty and thinks she's the reason Bellemere died.
You'd Expect: They would either gather the money in secret as well, seek help from outside the village, or at least talk to Nami. Sheriff Genzo ultimately tells Nami it wasn't her fault that Arlong was a murdering bastard, and she's not obligated to bargain for their lives. That's his job, as the town protector. It really wasn't her fault; Bellemere made a conscious choice to ensure her children wouldn't be hunted down and unceremoniously executed. As we see, more than a few pirates want a piece of Arlong— Sanji and Luffy included—- for hurting their navigator.
Instead: They let her suffer in silence to respect her wishes to handle this alone, despite the fact that Genzo is their Parental Substitute. It becomes a case of I Know You Know I Know and Nojiko smacks Sanji for saying he needs to defend Nami's honor.
The Result: The town only stands up to Arlong when he reneges on his deal with Nami, and that's when Genzo reassures Nami that their lives aren't in her hands but theirs. This leads to her breakdown and realizing that Luffy is the only person who can save them. She could have avoided eight years of suffering alone and betraying pirates if they had opened up earlier. - During Franky's backstory, he makes a series of stupid decisions that cause problems for years to come.
- Franky is able to build ships known as Battle Frankies, which are powerful enough to defeat Sea Kings and have his logo on them. Iceberg warns him to get rid of them before someone gets hurt.
You'd Expect: Franky to listen, or at least hide them in a secure location.
Instead: He leaves them where anyone can get at them.
The Result: Spandam is able to steal the Battle Frankies and use them to attack the judicial ship to frame Tom's Workers. - In the ensuing trial, Tom is able to use the pardon from building the Sea Train to save Iceberg and Franky from being sentenced to death for the attack, but at the cost of having his original death sentence for building the Oro Jackson upheld. As a result, Tom ends up being taken to Enies Lobby to be executed.
You'd Expect: Franky to do as Kokoro says and not resist, since it's impossible to save Tom.
Instead: Franky attacks Spandam, then tries to stop the Puffing Tom from taking Tom away.
The Result: Franky is nearly killed and forced to rebuild himself as a Cyborg. Much later, CP9 uses Franky's role in the incident as a pretext to arrest him to interrogate him for the blueprint's whereabouts. - After Franky's "death," he meets with Iceberg. Iceberg, knowing that the government is keeping tabs on him, gives Franky the blueprints to Pluton and insists that he leave Water 7.
You'd Expect: Franky to do as Iceberg says. Granted, Iceberg's secretary Kalifa was a CP9 spy, but this would have increased the chances of the blueprints slipping out of the World Government's reach.
Instead: Franky stubbornly stays on Water 7.
The Result: After CP9 raids the Galley-La headquarters to find Iceberg's blueprints, Lucci realizes that Iceberg gave them to Franky. With Franky still on Water 7, Lucci's team tracks Franky down and captures him the very same night.
- Franky is able to build ships known as Battle Frankies, which are powerful enough to defeat Sea Kings and have his logo on them. Iceberg warns him to get rid of them before someone gets hurt.
Super Rookies Era
- During the events on Conomi Island, Luffy is rescued from the pool and returns to fight Arlong. Arlong is aware of the Devil's Fruit users' weakness of being powerless in water, and he had put Luffy into the pool to begin with.
You'd Expect: Arlong to throw Luffy into the water again, thus putting him in trouble.
Instead: He chooses to gloat over how Fish-men are a higher race than humans, by talking about how humans are helpless underwater, among other things, and then fights Luffy on land. - Upon entering the Grand Line, the Straw Hats' ship is in danger of crashing into a giant whale. They slow down by firing the ship's front mounted cannon, but still sail into the whale. The only damage is the ship's figurehead being broken off and the whale doesn't notice them and starts submerging.
You'd Expect: The Straw Hats to wait for the whale to go, and continue on with their journey, reattaching the figurehead later on.
Instead: Luffy, angry at the whale for breaking his favourite seat, punches it in the eye. The whale notices, and swallows the ship in response.
Subverted: Believe it or not, this stupidity leads to Luffy learning about the whale's past, and befriending it. Its name is Laboon, and it is waiting on its old crew to return. This becomes very important when the Straw Hats encounter Brook for the first time. - During the Alabasta arc, after having escaped Crocodile's cage trap and making their way across the country, the Straw Hats know, or can guess the top remaining Baroque Works agents are waiting at the capital with orders to kill princess Vivi on sight. Since the rebellion sparked by Crocodile is already well underway, with rebels swarming in the millions towards the same city, they also know they are seriously pressed for time. The Straw Hats manage to draw the agents away with a clever scheme to give Vivi an opening to talk to the rebel leader and explaining the situation, thereby halting/stopping the whole war.
You'd Expect: All the princess had to do was run up to them, showing her face to the leader, who happened to be a good childhood friend who risked his life to save her from bandits at one point, and who would be certain to at the very least hear her out, which would've halted the rebellion and maybe stopped it before the fighting got serious.
Instead: She stops a few hundred meters in front of them, which at first seems smart, (not appearing as a charging enemy and all) but a mole in the army fires a cannonball that lands right in front of her, obscuring the view of both rebels and princess, thus stopping the attempt at stopping the war. It should be noted that Crocodile told her he had moles in the army, and she still stands within firing range of the city, with people who know what she attempts to do, and have orders to hinder/kill her to the best of their abilities.
Then: She gets badly trampled by the advancing army, only saved because her duck throws himself on top of her, saving her from the worst. And the war goes on as planned, resulting in the deaths of hundreds, possibly thousands, of combatants on both sides of the conflict before it is finally stopped. - While in Water 7, Usopp gets jumped by members of the Franky Family, beaten up, and has a large amount of the Straw Hats' money stolen from him, which they were planning to use to buy a new ship. He's understandably very upset about this.
You'd Expect: Him to stay on the Going Merry and recover from his injuries. Or, if he really wants to make up for losing the money, ask the other Straw Hats to come with him to the Franky Family's hideout as backup, and take the money back by force.
Instead: He decides to go to the hideout on his own. Virtually all of the Franky Family are there, and they beat the crap out of him. AGAIN. Granted, he was ashamed he lost the money in the first place, but that was still a pretty stupid move. - Shortly after Luffy and the others take down the Franky Family, Luffy has to break the news to Usopp that they have to get a new ship, since Usopp wasn't around when Luffy and Nami met with the shipwrights.
You'd Expect: Luffy to calmly and reasonably explain the situation to Usopp — that all the money in the world won't fix the Going Merry. In fact, Luffy himself couldn't accept the news at first, either.
Instead: Luffy starts off by cheerfully announcing the decision to get a new ship, while suggesting that they can go for a larger one with the money they have, inadvertently causing Usopp to assume that they don't have enough money to repair the Going Merry because he lost two thirds of the money. Luffy only brings up the fact that the ship is beyond repair after Usopp starts getting upset, and when Usopp protests, Luffy harshly (if correctly) points out that he's not a real carpenter.
Then: Luffy tells Nami to shut up when she intercedes on his behalf by bringing up how angry he'd gotten upon hearing the news. Luffy gets increasingly defensive about his decision, with the last straw being when Luffy tells Usopp to leave the crew if he can't accept the decision. Sanji kicks Luffy and tells him to get a hold of himself, but the damage has been done, and Usopp leaves. - In order to rescue Robin, the Straw Hats need to defeat each of the CP9 and get their keys. Unfortunately for Sanji, the first opponent he faces is Kalifa, a woman.
You'd Expect: For Sanji to either drop his feelings for women for once and beat her, or run away and try and find another opponent to fight.
Instead: He constantly lets her kick his ass several times. Nami even noted how stupid that was of him.
Then: She takes his place and is reduced to hiding with a Mirage Tempo. They both would've been screwed if Monster Chopper hadn't arrived. - Garp arrives at Water 7 while the Straw Hats are there recuperating from the battle at Enies Lobby. Since the captain of the Straw Hats is Garp's grandson, he decides not to capture them.
You'd Expect: That when it comes to Garp's report, he would either claim that the Straw Hats escaped him, claim that he found no trace of them at Water 7, or simply not mention them at all.
Instead: He outright states that he refused to arrest them because of his relation to Luffy. Unsurprisingly, Sengoku orders him to return to Water 7 and do his job once he gets the report. - Gecko Moria. Summary of the situation: The Straw-Hat crew are weakened after their fight against the super zombie Odz/Oars. Their captain, Monkey D. Luffy is himself severely worn out after using 100 shadows to temporarily gain the power to curb-stomp the aforementioned super zombie. Moria, angry at them, decides to finish them off himself. Since he didn't himself do much fighting this day, he is still in better condition than most of them, despite taking some strong blows from Luffy.
You'd expect: Him to use his power to absorb 200 or 300 shadows, which considering what 100 shadows did for Luffy, would have probably granted him enough power to easily crush all of them, while keeping control of the shadows, which he can do much better than Luffy since this power is initially his own.
Instead: He absorbs every shadow on the island to get a immense strength boost. Problem is, this proved to be too much to control, even for him, and the shadows started trying to escape. All the Straw-Hats had to do was to hit him hard enough in the stomach to make him spew out the one thousand shadows. Possibly justified as people who knew him in his prime remark on how he's let himself go. - In the final battle of One Piece Film: Strong World, Big Bad Shiki knocks Luffy into a massive pool of levitating water.
You'd Expect: Shiki to watch and wait for Luffy to drown since he was completely powerless to escape.
Instead: Shiki gloats a little at Luffy before attacking him again with Razor Wind, knocking him out of the water.
The Result: Luffy is free to continue the fight and eventually defeats Shiki. - Boa Hancock, ruler of Amazon Lily, is one of Seven Warlords of the Sea, as part of a treaty to protect her people and country from the World Government, who have some extremely powerful forces at their disposal. She's called upon to fight for them in the upcoming war with Whitebeard. Admittedly, she has a very good reason to hate the World Government.
You'd Expect: Her to grit her teeth and agree to fight Whitebeard, if only to keep the World Government off her back and protect her people.
Instead: She refuses, and not only that, she tries to rob the ship sent to get her and attacks the crew. Needless provocation at its finest.
Admittedly: As stupid as it sounds, Hancock does have a very valid point that she's so beautiful that she can practically get away with anything she wants. And, sure enough, she's not punished for her insubordination. When the World Government finally decides to end the Warlord system, it's mainly because of Crocodile and Doflamingo's actions, not hers. - What Chief Warden Magellan did during the Impel Down Arc could probably be considered the epitome of this trope. During said Arc, Luffy, Emporio Ivankov, and Inazuma manage to get down to Level 6 of Impel Down and free Jimbei and Crocodile. Shiryu (a former Chief Guard of the prison who is on death row in Level 6) witness this and tells the officers to pass word to Magellan about what happened, saying that he'll lend a hand with handling the escapees. There's also the problem of Buggy and Mr. 3 causing a prison riot and as if the situation couldn't get any worse, the Blackbeard Pirates have entered the prison and began wreaking havoc.
You'd Expect: Magellan would completely ignore Shiryu and retreat, along with all his forces, to the prison's entrance and make a stand there, since all of his enemies will eventually have to go there. In the case of Shiryu, it should be noted that he was imprisoned because he killed prisoners as a pastime, referring to his victims as "just trash".
Instead: He. Lets. Him. Out. The Chief Warden of a maximum-security prison authorizes the release of a ridiculously powerful Ax-Crazy Master Swordsman from Level 6, where the most powerful and dangerous prisoners are kept, because he thought he needed this psychopath's help.
Result: Shiryu refuses to play along, joins Blackbeard, and helps him, along with several very dangerous criminals, escape the prison. But worst of all, Shiryu takes it upon himself to kill as many people on the way out of the prison as he can for the sake of bloodlust, starting with the guards who released him.
Bonus Idiocy: Magellan had previously beaten Luffy with ease, and goes on to thrash virtually anyone who tries to fight him, thus showing that he didn't need Shiryu's help here. - Magellan's first fight with Luffy. Before the fight starts, Luffy is told that Magellan can poison anyone who touches him. Also, the reason Luffy's in Impel Down in the first place is to rescue his brother Ace, who will be taken away and executed in a few days.
You'd Expect: Luffy to either try and get past him, or attack Magellan in a way that doesn't involve him making contact with his bare skin.
Instead: He REPEATEDLY PUNCHES the guy. After all, it's what he does best and has worked against everyone else right? So against the guy who can poison anybody who touches him, it'll work without a problem.
Result: He's predictably beaten easily and fatally poisoned by the Chief Warden. He only survives thanks to one of his allies having the sense NOT to fight, and said ally being a Determinator in getting him to someone who can help. To make matters worse for Luffy, by the time he's recovered, it's too late for him to save Ace from being taken away from the prison. - Luffy and Ace, along with the remainders of the Whitebeard Pirates, are trying to flee Marineford. They run into Akainu, who begins to trash-talk Whitebeard, something that Ace doesn't take kindly to.
You'd Expect: They ignore the trashtalk and continue to hightail it out of there to their escape ship.
Instead: Ignoring his fellow shipmates' and even Luffy's urgings to ignore Akainu and his words, Ace takes the bait and starts a fight with the Admiral, someone who can injure him despite his usual intangibility, and ends up with a lava fist through the gut in order to protect Luffy when Akainu decides to go after him too. And unlike everyone else in One Piece, he actually dies.
New World Era
- From the Fish-man Island Arc, Vander Decken has used his Devil Fruit powers to turn a gigantic ship into a homing missile, and send it flying towards Princess Shirahoshi. Not wanting the ship to crush her homeland, Shirahoshi flees into the ocean, and the ship follows. Hody Jones is none too pleased with Decken's actions, and starts climbing up a large chain attached to the ship in order to sort him out. Luffy sees him, and wants to stop him from harming Shirahoshi. Remember that the ship is moving further into the ocean, and that not only do Fish-men like Hody have the Home Field Advantage over humans while in water, but Luffy has eaten a fruit that renders him unable to even MOVE in water.
You'd Expect: Either Luffy would ask his ally Jimbei to go after Hody and Decken, or Jimbei himself would offer to do so. Since Jimbei's also a Fish-man, fighting an underwater battle would be no trouble for him, and he's just as tough as Luffy, if not tougher.
Instead: Luffy decides to go after the pair of them himself. Sanji manages to launch him onto one of the chains, above Hody. Now this, on its own, isn't too idiotic, but...
You'd Then Expect: Luffy to jump onto the chain Hody's on, and knock him off it, and get Zoro or Sanji to take him out and stop him from getting back onto the ship. It's been established earlier that Luffy has Hody completely outmatched in melee combat, and Zoro and Sanji aren't that much weaker than him.
Instead: He goes straight for Decken. Although he's able to solve the water problem somewhat by blowing a bubble, Hody soon ends up nearly owning him when they're both underwater, and Luffy only survives thanks to Fukaboshi. - Mermaid princess Shirahoshi has one that surpasses even Magellan's in terms of facepalm-inducing stupidity. When she was a child, Hody Jones assassinated her mother, Queen Otohime, for wanting fishmen and humans to peacefully coexist. However, the incident was framed on a human, with the citizens of Fishman Island none the wiser. Shirahoshi learns this from her pet shark, Megalo, who witnessed the assassination firsthand.
You'd expect: For Shirahoshi to immediately notify her father King Neptune about what really transpired that day. Honor be damned, that's her mother that Hody killed, and he'll only keep killing for blind hatred's sake if nothing is done about him. Not only that, but Hody was a massive anti-human racist before he showed his true colors to the public, so him being the main conspirator behind the queen's death isn't entirely unreasonable, as far as Neptune and the rest of the royal family are concerned.
Instead: She keeps this information secret for years, not telling a soul, even her own family. All because she didn't want the cycle of hatred to persist by having her people understandably despise such a monster.
Result: By the time she finally comes clean with this revelation, Hody Jones and his crew have not only gained enough power and men to initiate a deadly coup, but Shirahoshi and her family (as well as Jinbei) are currently chained up and set for execution, and they all would have been killed had the Straw Hats not conveniently been on Fishman Island at the time. Hody even flat-out calls her an idiot for not informing her family of the truth the moment she learned it. - The New Fishman Pirates have managed to get their hands on a very powerful and potent drug - the Energy Steroid. It greatly increases the strength of the user, but at the cost of some of their lifespan.
You'd expect: For the New Fishman Pirates to use this drug sparingly, and only when necessary. Abusing a life-sucking drug such as that just might have dire consequences in the long run. Also, they're still drugs, so it's still possible to become addicted to them if the crew isn't careful about using them.
Instead: None of the crew take this into consideration. The officers OD themselves fighting Neptune's army and the Straw Hats, the biggest offenders being Hyouzou and Hody Jones himself, who gobble down the pills like they're M&Ms.
Result: Not only is their blatant substance abuse pointless, as the Straw Hats are able to completely wipe the floor with them anyway, but after they're finally defeated and imprisoned, the side effects of the steroids kick in, rapidly aging them into frail old men who can't even attempt to bend the bars of their cells open without fracturing their wrists in the process. Even if they had been successful in their takeover of Fishman Island, it would have been short-lived, as they'd be easily overthrown without much of a fight. Don't do drugs, kids! - Several of the Straw Hats have switched bodies thanks to the powers of Trafalgar Law. As Franky is heading out in Chopper's body, Chopper instructs him in the use of Rumble Balls: taking one will transform him into a massive monster that will give him immense strength for three minutes, but afterwards leave his body paralyzed for several hours. Furthermore, it took Chopper a long time to learn to control this body at all, and it would have been conceivable that Franky could not have done that either. He is naturally told to eat the drug only under an extreme emergency.
You'd expect: Franky to pocket the Rumble Ball and save it for when it is needed the most.
Instead: He eats it immediately and goes on a drug-infused rampage. - Usopp, Robin, and the Tontatta tribe are planning to take out Sugar, one of Donquixote Doflamingo's executives, as part of their strategy for taking the Warlord down. Sugar has eaten a Devil Fruit that allows her to turn anyone she touches into a living toy that can only do what she says. The plan is to force-feed her a grape that will render her unconscious. She's normally untouchable due to her bodyguard Trebol being constantly at her side, but some distractions cause Trebol to leave Sugar alone for a moment.
You'd Expect: Usopp to take this chance and try to shoot the grape into her mouth undetected, or at least have the dwarves slip the grape into her bowl of identical grapes.
Instead: Usopp refuses to fight, claiming that if he does so, he would quickly beat Sugar. And the Tontatta tribe, who severely underestimate Sugar's badassery, consider this a good reason for him not to fight. The Tontatta tribe then pretty much march into Sugar's room, announce their intentions, and Zerg Rush her. Because a little girl who can enslave anyone she touches could never be a dangerous opponent.
Result: The Tontatta are all beaten and turned into toys, along with Robin. The plan subsequently only succeeds because the good guys get lucky. - Trafalgar Law and Luffy are both in bad shape. The former is missing an arm and barely conscious, the latter has been immobilized with Trebol's flammable slime. After Law insults Trebol, he too is covered in slime and immobilized.
You'd Expect: Trebol to set the slime ablaze and wipe out both in one shot.
Instead: Trebol gets pissed off and walks up to Law to kill him barehanded while ranting about how Doflamingo is family. This is in spite of the fact that Doflamingo is yelling at him to step back because he's walking into an active Room. Law uses the opportunity to levitate his severed arm and severely injure him; he at least TRIED to pull a Taking You with Me after this by igniting the mucus, but Luffy got Law out of the blast radius just in time and Trebol only managed to knock himself out and was later arrested by the Marines. - Jack and his men are quite a bit worse for wear after a prolonged battle with the Mink Tribe when Jack hears about Donquixote Doflamingo's defeat and arrest and decides to go and forcibly bail him out. Upon reaching the fleet escorting him to Impel Down, Jack is informed that it is guarded by Sengoku, Fujitora, Bastille, Tsuru, and Maynard (among others).
You'd Expect: Jack to decide that it is simply not worth it. As monstrously powerful as he and his men are, they have absolutely no chance of winning a fight with that many heavy hitters, at least one of which could probably even give Kaido pause.
Alternatively: To trail the escort fleet while calling for any possible reinforcements before attacking. Getting his fellow Lead Performers like King and Queen along with the Tobi Roppo to help would boost his chances of success. Kaido might let any signs of weakness slide if it means getting Doflamingo back. It is a more preferable path than one that leads to certain failure.
Instead: Jack is actually offended by the notion that those odds would intimidate him in the slightest and goes straight for the fleet without a second thought. He managed to sink two of the ships in the fleet, but the end result was all too predictable: he got his ass kicked by the escort guards. - Not one to learn from his mistakes, Jack decides to make another big play with minimal planning not long after getting beaten to a pulp by Doflamingo's escort guards and goes straight for Zunesha, attempting to kill it and bring down all of Zou.
You'd Expect: Jack to assume that maybe killing an island-sized elephant (inhabited by the Mink Tribe, who are a) now very pissed at him and b) currently hosting the Straw Hats as well, who also have a bone to pick with Jack and Kaido) isn't going to be the easiest task and plan accordingly instead of just charging in like he usually does.
Instead: He immediately starts attacking Zunesha, who takes the blows until Momonosuke (who had the power to hear Zunesha's voice and command it) releases it from its orders to wander eternally, resulting in Zunesha annihilating Jack's entire fleet in one shot. Once again, he did survive, but it cost him his fleet and has left him completely helpless while he waits for someone to rescue him from the ocean floor.
At Least: Jack almost definitely did not know about Momonosuke's ability to talk to and command Zunesha. He's still suicidally impulsive and shortsighted, but that is not something that he could reasonably be expected to know. Not only that, his attacks left practically everyone on the island pinned down trying not to get killed by Zunesha's shaking, meaning that he doesn't have to worry about them attacking him at sea. On the other hand, Kaido probably did know, and given that Kaido was also aware that his underling was extremely prone to ill-reasoned spur-of-the-moment attacks on others where he essentially just relied on the hope that he was strong enough to survive whatever they threw at him, the argument could be made that some of the fault lies with him as well for not ordering him to turn back. - Periodically, Big Mom gets a craving for random sweets. This wouldn't be so bad, except that when this happens she goes on a complete destructive rampage, causing massive collateral damage and loss of life, and she won't stop until she gets what she craves.
You'd Expect: Her crew to have every single type of sweets nearby and on standby, just in case. Especially since Big Mom's territory consists of multiple Level Ate islands, and several of her crew and family members are Supreme Chefs, or can create sweets with their Devil Fruit powers.
Instead: No sweets are kept around. As evident, by her most recent rampage, every single time she flips out, her crew scrambles to find what they need, and perform a rush job each and every time to get it to her. - Nami comes off this way in Chapter 844. Sanji is forced to put up a front and tell Luffy and Nami that he really doesn't care for them or the crew he's been sailing with. To drive the point home, he kicks the shit out of a tired Luffy and asserts that what he's saying is true.
You'd Expect: Nami to suspect that something is wrong and that the lovable perverted cook she's been sailing with all these years would never mean what he's saying to them. Hell, she saw Robin do something similar to this during the Enies Lobby saga, and she herself put up a front during the Arlong saga, with Sanji suspecting something is wrong. At that point, he just joined their crew.
Instead: She slaps Sanji across the face and mockingly calls him "Lord" Sanji before telling him good-bye. It's pretty sad that Luffy of all people is the one who knows that Sanji is actually suffering from what he's done and he rightfully tells Nami to shut her mouth when she tries to argue that Sanji went "too far". Good thing she later realizes her mistake and apologizes to Sanji. - The Vinsmoke family wants to marry Sanji to Charlotte Pudding, but doesn't want to be brought into the fold under the command of Pudding's mother (and one of the Four Emperors) "Big Mom" Charlotte Linlin.
You'd Expect: Them to realize that such a thing is impossible and not even agree with the wedding/combination of their forces since it isn't what they want.
Instead: They believe they'll be able to convince Big Mom, someone who they KNOW keeps her many children close to her, have her daughters and sons-in-law live with them instead of her. And then use Charlotte Pudding as a hostage to force Big Mom to listen to them. Big Mom, a woman who only cares about her children as long as they're useful to her and her ambitions, would actually care about Pudding if she became their hostage and they revealed the wedding DIDN'T combine their forces like Big Mom wanted. They even comment on how it going the other way wouldn't work because they don't care for Sanji. - Some time ago, Caesar Clown accepted funds from Big Mom for his gigantification experiments, for she dreams of having her family members become as large as her so she can look them in the eye.
You'd Expect: Clown to manage the money wisely. Even if he can't create a perfect serum, he could use his work to curry favor with the Four Emperors and perhaps get extended patronage. However, remember Caesar is a total jerk.
Instead: He blows most of the money on booze and girls. And then has to meet Big Mom without any protection from Kaido or Doflamingo. - While the World Nobles are enormous assholes, one of them (Donquixote Homing) turns out to be a rather sweet guy and he's not happy with such a situation...
You'd Expect: For Homing to use his influence as a World Noble to do philanthropic work, or at very least to cut deals with the Marines to try making things better for others. The World Nobles are really, REALLY hated due to their assholery, so Homing's good deeds would start making people change their view of them or at least consider him as the exception to the rule.
Instead: He decides to renounce to his World Noble role and title, to live among the commoners. He does it without realizing that only the Marines' influence protected him and his family, and once he brings himself down to commoner status, the family is shunned and persecuted. His Delicate and Sickly wife passes out shortly after, he and his sons are almost tortured to death by angry mobs, and his eldest son Doflamingo (who's already not very well in the head) resents Homing so deeply for the family's poverty and blames him so much for the death of his mother that he ends up murdering him.
However: It is very likely that he could have succeeded in his goals if Doflamingo hadn't continued to act like a stereotypical World Noble and hadn't called unnecessary attention to the rest of the family, or Homing himself spilling the beans in the anime. Rocinante had the same upbringing as his brother and was always a genuinely good person, which lends great credence to his belief that there was something very wrong with Doflamingo that could only be blamed on innate nature. Without that giant monkey wrench that was Homing's awful son, the horrors that befell his family may have never come to pass. As for staying as a World Noble to use its influence, being the White Sheep meant that any action that benefits the normal people might get stalled or opposed by his 18 other peers, as it's implied when Mjosgard defends the Fishmen without leaving his position and hits Charloss, but Roswald plans revenge on him. - Luffy is stuck in Mirror World, a place only reached and exited with Charlotte Brulee's Devil Fruit ability. Charlotte Katakuri is also there in a practical death match against Luffy. Brulee has been forced to use her ability to serve the Straw Hats after being beaten and kidnapped, but has managed to escape capture. She has eavesdropped on Luffy's fight and is ratting out his allies' and crew's plans to the other Big Mom Pirates, and takes a moment to taunt him from the mirrors to try and injure his morale.
You'd Expect: Her NOT to go back into Mirror World PERIOD after knowing Luffy would gladly kidnap her, thus making it impossible for Luffy to leave and getting him trapped in a losing battle against the strongest son of the Big Mom Pirates.
However: Big Mom has succumbed to her eating disorder and has become a walking disaster destroying anybody who gets in her way as she fiends for a giant wedding cake she didn't get to eat.
Instead: Brulee predictably takes cover in the Mirror World from Big Mom's rampage in Totto Land and Luffy kidnaps her again the very instant he spots her and bails from his fight long enough to recover. Then, to cap it off, Katakuri points out how illogical it was for Brulee to return to Mirror World. - As Luffy continued dodging Katakuri's attacks, Flampe blows a needle into his knee, causing him to fall and get brutally stabbed by his strike, He immediately notices Flampe.
You'd Expect: Katakuri is reasonably pissed, but takes advantage of it and defeats Luffy, who was evolving and becoming a bigger trouble for him.
Instead: He criticizes Flampe and proceeds to actively wound himself to make things fair between him and Luffy and loses the fight by a hair's breath.
Moreover: Not to mention that Luffy himself has not done anything that justifies an honorable battle. From his perspective, since he arrived, Luffy has done nothing but kidnapped his sister, screw over his captain's mental balance, thus endangering his family, and not to mention has attempted to attack and succeed in attacking many of his siblings. - An amnesiac Big Mom has just made her way into the Wano Country and wanders into the Prisoner Mines; upon hearing about oshiruko, she develops a craving for it which, as anyone can tell you, is bad news. Queen (who is the overseer of the mines) hears her mention oshiruko and is angered by it, and is ready to guard his supply, only to be told by Babanuki to leave her alone and get ready to run.
You'd Expect: Queen to heed the warning. It's goddamn Big Mom. The Three Calamities put together would lose to her, let alone one of them, and if she's not mad at you, giving her the food she's craving will get her to leave you be.
Instead: Queen decides to defend his supply. She, predictably, whoops his ass, and the sheer force of the beating he receives frees Kid and Killer and badly damages Kawamatsu's cell door.
However: Luffy ate the supply beforehand anyways. Queen was fucked no matter what.
Furthermore: Queen did manage to defeat and capture her largely through sheer dumb luck (recovering enough to ambush her with one final, all-out attack that cured her amnesia and caused her to fall asleep, but didn't actually hurt her), but in the process of boxing her up for transport to Kaido's palace, he completely forgot about Luffy and left him free to rampage through the Prisoner Mines, with no one stronger than a Headliner available to stop him (and, as Luffy demonstrated with Holdem, a Headliner is nowhere near sufficient).
At Least: Considering that's friggin' Big Mom we are talking about, you can forgive Queen for putting all his attention on her and forgetting everything else. - Luffy, Zoro, Kid, Killer, and Law are fighting Kaido at the peak of Onigashima. It turns out Luffy has gained the ability to coat his body with Conquerer's Haki, and is now able to pierce through Kaido's defenses with his attacks. Turns out Kaido can do the same thing, and is naturally more experienced with it, being an Emperor far longer than Luffy has.
You'd Expect: For Luffy to keep Law and the others close together. Even as battered and injured as they are, Luffy still has a better chance of beating Kaido alongside them than going it alone. Remember that Law explicitly stated that their chances of winning against Kaido are 30%, at best - and that's if they fight together.
You'd ALSO Expect: Luffy, having been curb-stomped by Kaido before, would know just how strong his opponent is, and to not underestimate him - especially now that Kaido has gone One-Winged Angel and is no longer holding back, now that Luffy can legitimately damage him.
Instead: He tells the rest of the group to go off without him, foolishly thinking he can defeat Kaido by himself. This is while he's currently in cooldown mode regarding Gear Fourth.
Result: Luffy's arrogance gets him beaten into unconciousness and thrown into the ocean below Onigashima by Kaido almost as quickly as he began soloing him. Kaido even lampshades that he got too cocky after learning a powerful new technique.
Granted: Zoro's injuries were too severe and while Law could have helped Luffy needed someone to get Zoro out of the rooftop while Big Mom was so dangerous that Law would have been more useful against her. Luffy probably didn't see another option than fighting Kaido alone. - Despite the boy's new power-up, Kaido has defeated Luffy yet again.
You'd Expect: For Kaido to finish him off. He only kept Luffy alive the first time because he believed he would make a fine soldier, but all that got Kaido was a prison break and a war, so there's no point in keeping the pirate captain alive. In fact, killing one of the figureheads of Wano's liberators would certainly kill their morale and tip the scales of the war, and the Straw Hats would refuse to believe their captain is dead unless Kaido delivers Luffy's head on a platter.
Instead: Kaido throws Luffy off off Onigashima, guaranteeing that he gets rescued (which is exactly what happens). Kaido even muses to himself that he should've killed him precisely because of the reasons listed above. - After the events of Wano, Kid has decided to take on Shanks in revenge for his earlier defeat. Problem for Kid is, Shanks doesn't appear to take him seriously despite him aiding in the fall of Big Mom.
You'd Expect: Kid to wait patiently for Shanks to notice him. Despite being in the same category as the fallen Emperors, Big Mom and Kaido, Shanks has directly worked with Gold Roger, and even ignoring it, Kid to remember that he and Law barely won against Big Mom, with Kaido's munitions playing a major role in her defeat, and keep his guard up.
Instead: Kid, irritated that Shanks is not paying him any attention, decides to fire on his weaker allies. According to Shanks's Observation, Kid's Damned Punk cannon takes out several of his ships and killing numerous people aboard the ships.
Result: Shanks finally decides to take him seriously in order to prevent the future from coming to pass. He fires Divine Departure at Kid (and Killer) who dived in to protect him, as both get knocked out. His subordinates, finally getting the message, try to bargain with the Red Hair Pirates about the Road Poneglyphs they got from Wano, but Shanks, pissed off at Kid, orders Dorry and Brogy to attack Victoria Punk, destroying it and sending the Kid Pirates to the bottom of the sea.
