Brook/Personality and Relationships

Personality
Brook is an eccentric character with a distinct personality of his own, like the other Straw Hat Pirates.

While he looks like and claims to be a gentleman, he does possess vulgar and perverted manners such as asking to see women's panties (although in a mermaid's case he asks if they can lend him some money - however, he asked the former question to the Mermaid Princess anyway), yelling impatiently for food (a trait shared by Luffy), and occasionally burping and farting conspicuously. Despite this behavior, he still remains very polite and soft spoken in speech, usually referring to people using the respectful "-san" ("Sir") and always speaks to everyone even enemies in a very courteous manner. He appreciates the simplest of things: from a gesture of kindness, the company of others, and walking in the sunlight after receiving his shadow back. Brook was moved to tears at just being able to share a dinner with people after decades alone in the Florian Triangle.

Despite his eccentric behavior, Brook is an extremely upright and compassionate person befitting of a true gentleman as Brook utterly disdains wickedness and cruelty. When Zeo began to ruthlessly assault his own men, Brook even defended one of the enemies from Zeo's attack, reprimanding Zeo for his cruelty. Brook's compassion is shown in Zou where he was horrified by the immense devastation the Beast Pirates caused. He readily helped the badly injured minks along with his crew mates. After Luffy arrived at Zou, Brook gave specific instructions not to mention anything about Wano and samurais out of consideration for the minks. He even beat up Luffy after he expressed disappointment in not meeting Raizo.

His reactions to different occurrences can be somewhat extreme, often comically so. For example, when the Straw Hats were alarmed at him for being a living skeleton, he forgot the object of fear was actually himself and also began to panic. Although he tends to display more extreme emotions at times, Brook has been known to over-relax when he is told to stay calm. He is also very patient, having stayed on his former crew's ship for years, waiting for the day when he would eventually be reunited with his shadow. However, due to his rudeness, he can also be impatient about things like waiting for dinner to be served. Brook's most notable trait amongst others, however, is that he cracks "skull jokes" about himself being a skeleton complimented with his distinct laughter of "Yohohoho" even if there is no one around to hear him. When Chopper broke one of his jokes by saying what he intended to say beforehand, Brook became temporarily depressed.

While stuck in the Florian Triangle, Brook discovered his skeletal body was now very limber and developed a strange gag to keep himself entertained- going completely rigid and then leaning against a wall or object at a forty-five degree angle. Though he mainly uses it to show it off in front of people and his crew just for a laugh, Brook later turned this into one of his signature poses as the Soul King. He has sometimes practiced and attempted to tilt in even further than forty-five degrees, but if he makes the angle too acute, he will lose his balance and slip. He can even run around in circles while maintaining this pose- when Nami had him be a lookout as half the crew was headed for Zou, Brook struck his 45 degrees pose and didn't check any other angle, causing Nami to yell at him to look in every direction, so Brook began a 45-degree rotation, annoying her with his antics until she attacked him.

Brook is a great lover of music. In times of joy or sorrow, music is what generally keeps Brook going. When he was about to die during his first life with his fellow members of the Rumbar Pirates, Brook suggested playing and singing a song with their last breath. As a result, his love for music often reflects itself in various other aspects of his character, such as in his fighting style wherein the names of his attacks are derived from various songs and dances. He gave himself a musical theme so noticeable that while he was alive in his first life, he was called "Humming Brook" by the authorities.

In contrast to the other cowardly crew members' own fears - Usopp's being out of insecurity, Nami's as a survival instinct, and Chopper's from cautiousness - Brook's fear is more down to Earth; he fears the things that are not normal. An example would be that Brook is easily scared by the ghosts and zombies (despite technically being deceased himself). In order to fight the various Thriller Bark creatures without fear when he encountered them, Brook convinced himself that if he sings while fighting, he would not be afraid of them (though he starts running in fear when he stops singing). This singing while fighting, however, had a side effect of making him seem like a more sinister creature to the zombies - a rather ironic fact due to him being the contrary and the fact the song he sings during battle being one of life and joy than one of ominous threat and evil as perceived by them. Because of this, despite his equal fear he was given the name of "Humming Swordsman" by the zombies and was ironically feared by them in turn.

He apparently does not like moving fast, evident when he was in the more intense rides at Sabaody Park. Linked to this is moving at high speeds via the Flying Fish Riders flying fish or theme park rides and fighting a Pacifista cyborg there was little chance to win against. Comically, most of these fears are things he himself has the potential to unintentionally cause such as being an almost living skeleton that can run so fast that most people would have little chance to win against.

Before encountering the Straw Hats, Brook was very lonely while floating adrift on his ship and longed for the company of other people. He initially accepted Luffy's offer to join the crew and invited himself over for dinner upon arriving on board the Thousand Sunny just so he could interact with the crew and fill the void that he experienced all those years. Also, while possibly one of the oldest pirates "alive", Brook still retains an air of childishness about him that enables him to behave in a manner similar to Luffy and Chopper, noted by the ease with which he participates in their childlike antics.

His distinct personality and laughter allowed Nami, Usopp, and Chopper question a "guardian" of Hogback's lab, Ryuma, who had Brook's signature laughter and personality. This was because Ryuma possessed Brook's shadow until the samurai was defeated by Zoro, upon which Brook's shadow was returned to its rightful place.

Awkwardly, Brook has a tendency to lack common sense in slightly frantic times. For example, when Luffy falls into the water, Brook (and Chopper for that matter) jumps into the water, despite being a Devil Fruit user himself. He also has a tendency to accidentally go on rides that go obviously fast and sit out on slower rides.

Also in One Piece Film: Strong World, he appears to take offense if someone avoids him because he does not have any "substance", later commenting he is like that because he is "dieting". This was later seen again during the Punk Hazard Arc when Brook grew furious at a dragon for rejecting him, claiming that bones have plenty of nutrition. However, during the Zou Arc, most of the canine minks from the Mink Tribe constantly bit Brook due to him being made of bones, which he did not enjoy at all.

Brook believes in and has quoted the philosophy "Good things come to those who wait", given the years he spent on the ghost ship, and Laboon's patience.

And what would you know?! It's not like you've died before!!! Die and be left as a grudge!!? That's absurd!! Nothing is left behind!!! After death living things are just bones!!! People who waste lives... are what I hate the most!! That reeks of shame!! Not that I smell it without a nose~!!

However, one issue he has stood by is the act of wasting lives. As he had experienced death, he knows more than most about the consequences of dying. He shares a very strong emphasis on keeping promises and friendship, as he would do everything in his power to reunite and fulfill his promise to Laboon his long lost friend, something Franky had complimented him upon. Though he is prone to being childish, he proves a loyal and fearless friend. Standing between Usopp and a Pacifista stating that he shall protect him even though he knew his chances of survival were slim. Even Zoro has quietly acknowledged that Brook is a true man to his heart, facing down odds that are near impossible unflinchingly to save a friend. As possibly the ultimate example of this, he shows absolutely no fear in the face of Big Mom, a Yonko, who is specifically able to use an opponent's fear against them. He even goes so far as to call her "young lady" during their fight, an unprecedented sign of contempt for someone of a Yonko's status.

Like Sanji, Brook's mind is often filled with lecherous thoughts. Ironically for his relationship with Sanji, however, two women whose beauty Brook has explicitly complimented are Vinsmoke Reiju (Sanji's elder sister) and Charlotte Pudding (Sanji's arranged bride); in the case of Reiju, Brook even expressed regret at not having lips with which to receive a kiss from Reiju. Brook is also chivalrously protective over women (as is Sanji), as he chastised the New Fish-Man Pirates for aiming their firearms at Shirahoshi. However, unlike Sanji, Brook is not against fighting a woman to protect his friends or to complete an important objective. He defeated Jora to cancel the effects of her Devil Fruit powers and battled against Big Mom to keep the copied writings of the Poneglyphs safe.

Though he knows other songs, Brook's favorite song to sing is Binks' Sake which he was singing upon his first appearance. Even when he asks for requests from the others, he seemed to instantly switch over to singing this song. Other songs Brook sings include Black Handkerchief of Happiness and his own originals, Bone To Be Wild and New World.

Brook is also clever enough to trick Jora into turning his weapon back to normal by pretending to side with her.

He loves to drink tea, as he is often seen holding a cup of tea.

Brook's attitude of waking up the crew in person is seen when he woke the Rumbar Pirates with his song White Handkerchief, much to his old crew's annoyance. His attitude carries on to the Straw Hats when he woke them up in person, much to their annoyance once again.

Rumbar Pirates
As a member and eventually the second captain of the Rumbar Pirates, Brook and his crew were very close friends, and was akin to family. They all enjoyed music and each other's company, and Brook was amongst the sad when Captain Yorki and half of the crew contracted an incurable illness that forced them to be separated to prevent it from spreading to the other half. The remainder of the crew trusted Brook to the point of appointing him as the succeeding captain. When the remainder were wiped out by a force that used poisoned weapons against them, Brook alone shouldered the crew's promise to reunite with Laboon, and became lonely and depressed when everyone else died.

Straw Hat Pirates
The Straw Hats were immediately wary of Brook prior to his initial entry into the crew (save for Luffy, who invited him on board the Thousand Sunny), but this changes after the events of Thriller Bark.

Despite his obnoxious personality, Brook deeply cares for his crew, going so far to protect Usopp and Sanji from Kuma. His eccentric personality often gets on the crew's nerves, showing no appropriate respect for Nami and even Robin when he asks to see their panties, and makes skull jokes in serious situations which often lead to him being beaten up, even shattering Robin's normally limitless patience. This is likely due to his long years of isolation with no real human contact.

Nevertheless, Brook's sense of humor and music can enlighten an organization as big as the Thriller Bark Victim's Association. Franky is moved to tears upon hearing Brook's backstory, and the rest of the Straw Hats gain respect for him, even Usopp and Chopper who were initially afraid of him, after hearing about his devotion to keeping his promise to Laboon.

During Brook's fight with Charlotte Linlin, he says that the "worst case scenario" for the Sanji's Retrieval Team is if Sanji deciding to not rejoin the crew, and when asked about it by Big Mom, he refused to presume that any of his friends would die during their mission.

Monkey D. Luffy
Before he officially joined the crew, only Luffy made friends with him, due to finding him hilarious as well as being amazed to see a living skeleton. The two even goofed around in the same manner during their dinner on the Sunny. As Brook explained his thoughts, Luffy was not afraid of him and even offered him a place on his crew. This was enough to make Brook happy after being alone in the dark for so many years.

Brook seems to respect Luffy a lot and unlike most of the crew members, he follows the captain's rules without question, going on record to state that he only follows Luffy's orders.

After the time-skip, Brook gave up the life of a music star to rejoin the Straw Hats as he was indebted to them and Luffy for accepting him. He was also amazed at his captain's improved strength as he defeated Surume. His loyalty still remains and is even fiercer as he told Zeo that his captain will become the Pirate King.

During Brook's fight with Charlotte Linlin, he described Luffy as someone who would break through any and all walls in order to pursue his beliefs and ambitions, showing his admiration for his captain's spirit.

Roronoa Zoro
In their first meeting, Zoro was very disturbed and confused by Brook's skeletal appearance but after hearing about Brook's connection to Laboon and saving him from Ryuma, Zoro began to enjoy the undead skeleton's company. Brook is indebted to Zoro for defeating the undead samurai which gave Brook back his shadow and Brook was further amazed when Zoro along with Sanji offered their own lives instead of Luffy's to Kuma. Brook also shared a laugh with Zoro about his recent induction into the crew, stating the skeleton had bad luck.

After Zoro recovered from his pain, Brook informed him of his entry in the crew as Zoro jokingly told him to be prepared for the craziness it holds. As the two swordsmen of the Straw Hats, Brook and Zoro get along very well. Brook is in awe of Zoro's sword skills, although Brook is 69 years older than Zoro.

After the time-skip, they still get along though they argued on Punk Hazard when Zoro called him "grandpa".

Nami
Nami was terrified of Brook when she first saw the skeleton and hid behind Sanji, but after she got to know him better, they formed a rather comical relationship. He can often be seen with Nami, as well as the "weaker" members of the crew (Chopper and Usopp) crying over scary situations, such as when Donquixote Doflamingo closes in on the Thousand Sunny for an attack. A recurring gag between Brook and Nami is that Nami will often kick Brook in anger when he asks to see her panties; to which her response usually entails something like, "As if!" or "Why the hell would I?!". As she will with other crewmates, Nami will hug onto Brook when she is scared (much to Brook's joy). Nami trusts Brook as much as she trusts the rest of her crew. She also enjoys listening to his music. She was also impressed that he managed to copy Big Mom's Poneglyphs, hugging him and congratulating him for his success though she kicked him when he asked to see her panties as a reward.

Nami can be very rude and short-tempered with Brook at times, albeit the skeleton often gives her reasons to be angry at him due to his comical and perverted nature. This frequently leads to Nami hitting him over the head.

Usopp
Usopp was naturally terrified of Brook when he first appeared on the crew and tried to ward him off with a crucifix, being against the idea of Brook joining the crew even after finding out he was harmless. Usopp at the time stated "I wouldn't be able to sleep with a skeleton walking around". Only after hearing about Brook's connection with Laboon and subsequent battle at Thriller Bark, did Usopp finally trust the musical skeleton, accepting Brook as a crewmate. Usopp loves when Brook plays songs, in particular Binks' Sake.

Usopp, like the rest of the crew (except Luffy), finds Brook's skull jokes annoying, especially when they are unbelievable like Brook trying to heal himself with milk, saying that calcium doesn't work that fast. After the time-skip, Usopp admitted to be jealous of Brook's new ability to phase through walls, citing its perversion potential.

Sanji
Sanji was one of the first members of the crew to meet Brook. He was shocked to see a walking and talking skeleton, and questioned Brook on how he came to be. Sanji couldn't understand why Brook seemed so constantly upbeat, telling the skeleton that his life was depressing, but the skeleton laughed him off. After Sanji learns about Brook's connection with Laboon, Sanji joined the rest of the crew in supporting Luffy's decision to recruit him into the crew. Sanji still gets irritated at Brook's immature character traits, including his burping and farting during dinner, and by his lame 'skull jokes'. He also once threatened to attack Brook when the latter laughed at the resemblance between Duval and Sanji's first, hand-drawn wanted poster.

However, Sanji has a lot of similarities to the un-dead musician. Both of them wear suits and act like gentleman and fawn over Nami and Robin, making them the "pervert duo" of the Straw Hats. While they do fight over Nami and Robin's affection, the cook and the skeleton are good friends and were both (along with Kin'emon) very jealous of Momonosuke's "special attention" from the ladies. Brook looks up to Sanji and was in awe when the cook battled Doflamingo and was even prepared to aid him when Sanji was in trouble, but Sanji instead trusted Brook to look after Momonosuke, Nami, and Chopper. Brook was very depressed over the outcome of events in Zou, and insisted on joining Luffy in the Sanji Retrieval Team as he felt responsible for Sanji's capture. Like Robin, Brook was aware of the Vinsmokes and never thought Sanji would be connected to such an infamous family. Along with the others, Brook showed great surprise that Sanji turned down Pudding.

Sanji appears to have a lot of trust in Brook's strength as he once entrusted Nami's safety to the skeleton while he went on to explore Claw City. Brook was also the only crewmate Sanji asked to accompany him when he had to deal with Pekoms and Capone Bege.

On a more humorous note, Brook was also very jealous of Sanji after meeting Charlotte Pudding, Sanji's arranged bride.

During Brook's fight with Charlotte Linlin, he described Sanji as a kind man that would refuse to budge once he decided to sacrifice himself for the sake of other, showing his admiration for the chef's spirit. He claims that his mission to retrieve the information from Big Mom's Road Poneglyph is so Sanji wouldn't feel like his friends' journey was for nothing.

Tony Tony Chopper
When Chopper first met Brook, he was terrified of him because he was a walking, talking skeleton and agreed with Usopp that he would not accept him as a crewmate. But after hearing the story about Brook and Laboon, Chopper cried and stated he was not afraid of skeletons anymore. Chopper and Brook get along very well despite Brook being the oldest Straw Hat and Chopper being the youngest. Chopper loves the undead skeleton's music and will often dance to it.

Nico Robin
When they first met, Robin stood there emotionless and, similarly to how she responds to Sanji's advances, did nothing when Brook asked to see her panties. Robin did find Brook annoying when he started cracking jokes instead of telling them how to stop Zombies and had difficulty stopping Franky from hurting him (she eventually let Franky do so). Nonetheless, they are on comfortable, friendly terms with each other. Robin seems to hold Brook to high standards as the oldest member of the crew and finds it slightly annoying when he doesn't act his age. With that said, however, she is still very fond of Brook and especially his music.

Franky
At first, Franky seemed to be very annoyed with Brook's skull jokes, often threatening to shoot Brook when he did them, as well as beating up Brook on Thriller Bark after he went too far. He soon questioned Brook about his past and after listening to his story, he became rather fond of him. This led Franky into accompanying Zoro to head after Ryuma to help get Brook's shadow back. After the battle against Gecko Moria had ended, Franky, alongside Usopp, built an impressive memorial grave for the Rumbar Pirates which deeply moved Brook. After Brook's entry in the crew, the two get along very well as the two oldest members.

After the time-skip, Franky revealed that he was aware of Brook's status as a famous musician, expressing an unsure attitude of him returning to a life of piracy. He was soon surprised that Brook actually gave up such a life and welcomed him back to the crew when they reunited. They still get along and often share jokes.

Jinbe
Brook, along with the rest of the crew besides Luffy, met Jinbe first on Fish-Man Island. When Jinbe had retracted his attempt to leave the Big Mom Pirates, Brook thought something was wrong as he thought the Jinbe he came to know is not a coward as the Totto Land News made him out to be, and was more understanding of Jinbe's decision than the scorning citizens of Totto Land.

The respect is reciprocated on Jinbe's side, as he complimented on how Brook faced a Yonko and hid the Poneglyph copies from her.

When Jinbe told the Sanji Retrieval Team to press forward after Pedro sacrificed himself, Brook was at first infuriated that Jinbe was acting so insensitively to a comrade's death before being told that it was what Pedro would have wanted.

Laboon
In addition to losing our crew, my face, my body, I've lost it all. Even if we met again you wouldn't recognize me at all in this skeleton form. I don't have anything left but they all said... this head of mine made you laugh...!!! I'll protect this look to the end because I'm coming to see you. I just hope you're waiting at our promised cape...!!!



Over fifty years earlier, Laboon met the Rumbar Pirates after becoming lost and separated from his pod and began following them in his loneliness. After a while they notice how sad he looked and they cheered him up by singing and as a result he continued to follow them. The crew grew attached to him because he was "cute". Eventually, while feeding him bait, Brook named him "Laboon". He was accepted as a crew member and even aided them when an attack left a few crew members having fallen overboard and no one else could help them.

Brook cares a lot about his afro. Because it is the only part of him that did not rot away after he died, it means a lot to him. It is the only thing he believes that Laboon would still recognize him by after fifty years. Since it will not ever grow back again should it be cut, Brook is extremely protective of it. Because of the promise Brook and the rest of his crew made to Laboon, Brook feels obligated to meet up with Laboon in order to fulfil that promise. He feels that Laboon would not forgive them for dying irresponsibly in the Grand Line. Brook later learned from the Straw Hats that Laboon is still waiting at the Twin Capes, resulting in him becoming overjoyed that he can now continue his late crew's promise. During the From the Decks of the World: The 500,000,000 Man Arc, Laboon is shown very happy after learning of Brook's new bounty indicating he is aware of Brook's survival and involvement with the Straw Hats.

Crocus
Fifty years before the current storyline, Brook first met Crocus when Rumbar Pirates entered the Grand Line through Reverse Mountain from the West Blue during which time he became acquainted with the Brook and his crew while they where staying with him at Twin Capes Lighthouse as their ship was being fixed in preparation for their journey into the Grand Line. Since Laboon was too young to follow them the Rumbar Pirates entrusted the young whale to Crocus. Crocus agreed to watch over Laboon until the pirates came back from sailing around the world and came back down Reverse Mountain again. However despite the Brook and his crew's promise to come back after two to three years, Crocus did not meet them again at the promised time and waited much longer.

Twenty-six years before the current storyline, Crocus ended up joining the Roger Pirates in order to find out what happened to Brook and the rest of the Rumbar Pirates. Crocus discovered a report that stated that some of the Rumbar Pirates had tried to escape the Grand Line through the Calm Belt. Crocus believed that the entire crew had fled the Grand Line in cowardice and broken their promise to return to Laboon, unaware of their tragedies and Brook's condition. After the Roger Pirates disbanded, Crocus returned to Twin Cape to tell Laboon what he believed had happened to Brook and the crew, however Laboon refused to believe him and started bashing against Reverse Mountain in an attempt to rejoin his pirate comrades. Despite his belief that the crew had broken its promise to Laboon, Crocus continued to care for the whale in their place. It is unknown if Crocus has learned of Brook's survival since he became the world famous musician, Soul King. However, during the From the Decks of the World: The 500,000,000 Man Arc, he and Laboon were seen reading a newspaper detailing the Straw Hats new bounties. It can be assumed Crocus now knows of Brook's current condition and his status as one of the Straw Hat Pirates.

Fans
During the two year timeskip, Brook became a world-famous celebrity and had flourished so much in his career as a music star. By the time he was seen again in Sabaody, he was ready to conduct his final concert for his hardcore fans before returning into piracy once again. His fans were shown to be quite devoted to him, tolerating the fact that he was a walking, moving skeleton, and were greatly saddened when the Marines publicly declared Brook's past identity as a pirate and possible membership in the crew of the Straw Hat Pirates. They were even willing to brush off the attempts of the Marines to apprehend Brook when he announced that he will perform one final song for them to hear.

Mink Tribe
Due to his group's efforts in saving the Mink Tribe after they were devastated by an attack from Jack, Brook and his crew are considered as saviors to the minks. Therefore, they formed a harmonic relationship. Because Brook is literally made only of bones, he gets scared whenever he would come face-to-face with the "Canine" species of the minks. In turn, they call him "Baron Corpse" to show affection to the person they love to bite on so much. When Brook was departing Zou on a quest to rescue Sanji from Big Mom, many of the canine minks requested to be allowed to accompany the Sanji Retrieval Team just so they could continue chewing on Brook's bones.

Pedro
Pedro joined the Sanji rescue attempt from the Big Mom Pirates, and was paired with Brook as a side mission to get Big Mom's Road Poneglyph. Brook and Pedro both agreed that Pedro will be used as a distraction so that Brook would copy the poneglyph information, an act that Brook considers as another reason to complete his task and "save face".

When Pedro and the others rescued Brook from Big Mom, Pedro apologized to Brook for putting him through so much danger with the Yonko, but Brook revealed that he accomplished his task and thanked Pedro for his efforts.

When Pedro sacrificed himself in a kamikaze attack against Charlotte Perospero to give the Straw Hats an opening to escape, Brook was among the ones who mourned for him. When Jinbe spoke in such a way that made them think they should just look past this and move forward, Brook was angry at Jinbe for taking Pedro's death so lightly.

Enemies
While alive, Brook encountered many enemies during his journey through West Blue and the Grand Line, including the group that killed him and his crewmates.

Marines
He also received a bounty from the Marines in this time, and due to his managers betraying him, Brook's existence as a pirate and affiliation to the Straw Hats has been revealed to the Marines. His bounty remains active and following the defeat of the Donquixote Pirates, he receives a new bounty and wanted poster (which uses one of the promotional posters from his concerts) along with the rest of the Straw Hat crew.

Thriller Bark
Because of the mess he made five years ago in Thriller Bark, three of the Mysterious Four know how troublesome he is. Dr. Hogback, in particular, greatly fears him, mainly because Brook once had him at sword point five years ago and learned the weakness of the zombies. Only Perona does not know of his doings because she was asleep at the time and ignored Kumashi's attempts to wake her.

Ryuma
Brook's main enemy from his time on Thriller Bark was Ryuma, the zombie that was animated with his shadow. After Brook was set adrift at sea, he returned to the island in search for his shadow. After causing some problems on the island, Brook came across Ryuma who possessed his shadow, and while they shared the same techniques, Ryuma had the stronger body and was able to best Brook at his own fighting style. Knowing that he could not kill Brook (because if the original owner of the shadow is killed, their shadow is destroyed and the zombie becomes a lifeless corpse again), Ryuma let Brook go with a broken skull.

Later, while sitting down and drinking tea in Hogback's lab, Ryuma is confronted by Brook. The skeleton then challenged Ryuma to a duel. After several bone shattering strikes, Ryuma easily defeats Brook with his own style. Ryuma then grabs Brook's afro and decides to cut it off as a final blow towards the skeleton. However just before Ryuma could cut off the afro, the entire island suddenly shakes and makes Ryuma lose his grip on the afro. Franky then arrives in the lab to tend to Brook. Ryuma, upon regaining his balance, attacks both Franky and Brook. However before it hits its mark, Zoro blocks Ryuma’s attack and challenges to fight Ryuma himself in Brook's stead.

Managers
Brook's managers were bandits on Namakura Island, led by Sancrin. Two years ago they used to steal and kidnap from the people of Namakura Island until they were virtually penniless. After kidnapping a young girl, Brook wrote a song that encouraged the locals to fight back and capture their tormentors. The people of Harahettania planned on displaying them as freaks, but were convinced by Brook to let them go. However, as a result, they kidnapped Brook and instead put him on display as a freak show at their home island of Kenzan Island. They were worried at first when he did not move and asked him to do so. They were then surprised when he suddenly started performing for everyone.

Two years later they have apparently become quite close with Brook, as they are now dressed up in suits and have become his managers; however, it was soon revealed that this was only because they only saw him useful for getting rich, as after Brook informed them about his plans for retirement, they betrayed him by calling the Marines (in spite of this, Brook was still grateful for their care over the last two years). They were last seen at the concert hall, furious about Brook's escape. During From the Decks of the World: The 500,000,000 Man Arc, they are shown stabbing Brook's new wanted poster which clearly shows they are still angry at him for leaving them.

Charlotte Linlin
When Brook came face to face with Big Mom, he was truly terrified at seeing one of the Yonko while Big Mom was very interested in Brook being a living skeleton. During their fight, Big Mom overwhelmed him and soon questioned Brook's motives before ridiculing his optimism. Brook told her not to underestimate the will of his crew before standing firmly to tell her that he will be taking the Poneglyphs in her possession. During the fight, Brook managed to damage Prometheus, a feat which Big Mom unabashedly praised later.

Despite Brook's efforts, he was defeated by the Yonko who mocked him by treating him as if he were a pet as the latter felt humiliated by his loss. Brook was further shocked when he listened as Big Mom conversed with Pudding about their intention to slaughter the entire Vinsmoke Family, Sanji included, during the faux-wedding ceremony. Despite his defeat, Brook was able to create copies of the Poneglyph text before Big Mom caught up with him, and with the help of his comrades, ultimately escaped from her grasp with them. Charlotte Brûlée and Diesel were shocked and horrified at this revelation.

During the tea party, Brook dealt a powerful blow to Big Mom by disguising himself as one of Luffy's duplicates, slipping past her, and destroying the picture of Mother Carmel, her most treasured item. Big Mom was very surprised to see that Brook is still alive after he revealed himself and left her in a state of shock at his action. Linlin swore to never forgive Brook for destroying Carmel's portrait. Despite his animosity towards her, Brook asked to look at her panties as she was chasing the crew.

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