The art of the sad backstory is a time-honored trope in all of anime, and this is no different for One Piece and its harsh waters. While the pirating life may look glamorous, its history is rife with the pain and sorrow of a corrupt government, a vain society, and just generally flawed people.
When these elements come together, nothing good ever really happens, and some genuinely shocking events come to haunt the One Piece world. This list will try to work through the tears, as it ranks the saddest and most powerful backstories between the One Piece characters.
10 Señor Pink
Even gangsters fall in love, but that doesn't mean the pirate and social life can mingle. After marrying a woman named Russian, tragic events would befall when Señor Pink wouldn't be able to be there when his own son became sick. This would force Russian to discover Pink's dark past herself, leaving her to overreact and befall an accident of her own that left her near brain dead.
The only way that he could make her smile now is by wearing the old baby clothes that their son once wore besides the ridicule. If anything, it added to his inherent stoicism, as the hilarious demeanor comes off as nothing less than badass.
9 Tony Tony Chopper
Being a blue-nosed reindeer that ate the Human Human Fruit, Chopper was just bound to be ostracized by both human and reindeer societies alike. However, one person was able to see past the strange features and befriend and help him like anyone else. That would be the criminal turned doctor, Dr. Hiluluk, who took Chopper in as his own son and medical apprentice.
Unfortunately, Hiluluk himself had an incurable disease, one that Chopper tried to cure himself by unwittingly feeding him a poisoned mushroom. Not one to be discouaged, Hiluluk, in his last hours, still took the time to run to the aid of his kingdom's doctors, despite the fact that he was obviously being trapped by its corrupt king. These events would give Chopper the sense of unprejudiced heart and romanticism that make him who he is today.
8 Monkey D. Luffy
Luffy surprised many of his fans with his uncharacteristically cheery backstory. That's not to say that Shanks losing his arm wasn't heart wrenching, but it's a little tame for a Shonen protagonist origin story. Fortunately/unfortunately enough, Oda would go deeper into his life later on, when he revealed the tragic tale of his brotherhood with Portgas D. Ace and Sabo.
Such a history was rife with both growing kinship and the tragedy of poverty, corruption, and class differences, things that came to haunt Ace and inevitably "kill" Sabo. People know why Luffy wants to be a pirate; but now, they know why he hates crybabies, why he has a problem with rich people, and why he cares so much about defending his friends and family.
7 Nami
Nami was an orphan of war who would be taken in by a Marine, one who struggled to raise her and her sister as both a single mother and a poor member of her community. The latter would come to haunt them, when the Arlong Pirates invaded their village and demanded ransom in exchange for their lives.
Nami's mother was only able to pay for Nami and her sister. Throwing on top Arlong's subjugation of her and her long journey to try and buy back her village, and there's little ambiguity as to why Nami is as greedy as she is.
6 Sanji
Sanji is another character with a two-part backstory, and unfortunately for him, both of them are really sad. The first involves his trying history with "Red Foot" Zeff. A pirate raid gone wrong and a terrible storm would bring the two together by stranding them for days on end on a lone island. This would force Sanji to go through starvation and his future master to eat his own leg.
This is already pretty dark, but it doesn't compare to his years of loss and abuse at the hands of his biological father. As a member of the infamous Vinsmoke Sanji, Sanji was expected to be a powerful soldier, despite his love of cooking and kinder tendencies. His family would not only resent him for this but even imprison him to hide their family's shame.
5 Boa Hancock
Boa Hancock and her sisters were kidnapped at a young age by slave traders. This would subjugate them under the direct rule of the Celestial Dragons who branded them and forced them into a long history of ridicule and torture for their own amusement.
It wouldn't be until Tiger Fisher's selfless liberation of Mariejois that she and her sisters would be freed, but the psychological trauma had already done its work.
4 Donquixote Doflamingo
Doflamingo was once a Celestial Dragon whose family forsook the title to live a humble life among the peasants. However, this wouldn't absolve them of all the prejudice associated with the nobility's evil, and they were targeted by their new community as scapegoats for years of pain and torture.
His family was forced out of their new home, hunted down, and made to live in poverty. His mother would die of some illness, and Doffy himself would try to earn back his family's status by killing his father. When this didn't work, he'd turn to piracy as a means of getting back at peasants and nobles alike.
3 Brook
As it turned out, Brook was one of the pirates from long ago that befriended Laboon when the whale was just a baby. They genuinely meant to return to their old friend again, but tragedy kept them from doing so in one piece.
Brook's captain would die of a mysterious illness; and under Brook's command, the rest of them would be killed off when they were ambushed in the Florian Triangle. Having eaten the Revive Revive Fruit but having no means of escaping the triangle on his own, Brook would be subjected to more than 50 years of isolation on the sea surrounded by the dead bodies of his lost comrades.
2 Nico Robin
Everything about Nico Robin's backstory just hurts. She had a Cinderella-esque upbringing, when her mother left her in the care of some less-than-kind relatives who made her work like a dog while they showered their other child in praise. This wouldn't discourage her, however, because she'd befriend her country's community of archaeologists and learned their trade.
That same knowledge would, unfortunately, lead to their demise, as the World Government feared what they had learned and decided to destroy the entire country, people and all. Robin was forced to see new and old friends alike as well as her own mother die at the hands of the Marines. She would then be forced to travel the world alone, hunted down by the government and recreating her country's research on her own.
1 Trafalgar Law
The only thing that can top how sad Nico Robin's backstory was is the never-ending tragedy of Law's. Government greed and oversight would not only result in his country being inflicted with an incurable disease, but their own ignorance had the country and its people burned to the ground. Law, having escaped in a trolly of dead bodies, eventually found his way to the Donquixote Family, where he begged to join as an agent of destruction.
As fate had it, he would be taken in by a double agent within their ranks, Corazon, who took Law away from the pirate life and tried to show him the good in the world by taking him to hospitals from all over. Unfortunately, Cora would only prove Law's distaste for humanity as a whole. It wouldn't be until Cora sacrificed himself to get Law the Devil Fruit that would save his life that Law would see the kindness of some people and embark on a new journey to avenge his old master.