When he was a teenager, Danjuro failed in his classes and repeated many grades, almost destroying his dream of wanting to be a hero. One day, he was called into the office of his school and told that he would be expelled if he did not improve. Later that day, Danjuro accidentally got in the way of a hero trying to save a window cleaner falling from a skyscraper.
While Danjuro tried to jump to the rescue, the Pro Hero bounced from the elastic surface Danjuro had created, making the hero too late to catch the falling man. The window cleaner received severe injuries and Danjuro was expelled from his school. Both his parents no longer supported him, therefore making him give up on his dream of becoming a hero and he left their house.
At the age of 22, while unemployed, he met an old classmate Takeshita who had become a successful Pro Hero. However, he did not recognize Danjuro when the latter greeted him. This traumatized Danjuro and made him realize that he was not fit to become a hero.
Six years later, Danjuro had become known as the villain of the media world, though he has been mostly unsuccessful at gaining popularity during his criminal career.
However, his videos inspired Manami Aiba, a young woman who was going through a deep depression. Desiring to meet him, she used his computer skills to locate Gentle, who welcomed her with open arms. After spending time together, Gentle decided to make Aiba his sidekick and gave her the villain name La Brava, believing that they will be the perfect combo.
Danjuro is robbing a store, as some Heroes try to stop him. He easily defeats them as La Brava records him. The new villain reveals himself to the world to be Gentle, a fancy and lavish-style villain, and tells La Brava that they will be going. Gentle wishes for his name to be etched in history. On top of a building, La Brava informs Gentle that their video of the store robbery is getting a lot of views. Gentle sees that he will have to accomplish a lot more if he wants people to start taking notice of him. While pouring tea, Gentle tells La Brava that he is searching for something that will make him extraordinary.
Gentle explains that he commits crimes for reasons such as attacking the J Store for hiding expiration dates of Fluffy Pudding that was about to expire even though there was evidence about the misgivings of the sales. Despite this, the pudding company selling the pudding feigned ignorance and tried to sidestep the matter. Gentle explains that he hands out punishments to those who do not act "gentlemanly" and is the Chivalrous Thief. When La Brava becomes infuriated that the video has not got any views. Gentle and La Brava think that Stain's biographical video stole the spotlight from them. Gentle talks about his next project which involves U.A. High School's Culture Festival. As the school was fortified after being attacked and is the current symbol of the Heroes, Gentle believes that if he invades the festival, then he will become the center of attention.
The next day, Gentle is seen working non-stop. As La Brava goes to fetch some tea, Gentle notes that dissatisfaction is growing towards Heroes nowadays because of their feeble-minded nature. Gentle praises U.A.'s preparations but criticizes their resourcefulness when faced with the unpredictable. La Brava wonders if Gentle will involve the U.A. students, he replies that simply invading U.A.'s School Festival in and of itself is a wake-up call for them to grow stronger, which La Brava finds cool. On his computer, Gentle decides to double check the route they will take to get to U.A.'s School Festival.
On the day of the attack, a disguised Gentle and La Brava run into Izuku Midoriya. Izuku apologizes while the disguised Gentle is more worried about losing the aftertaste of the Golden Tips Imperial tea he had just drunk. Gentle and La Brava attempt to leave wanting to avoid further contact. Hearing them talking about coffee, Izuku notes that the house was a coffee shop which grabs Gentle's attention. Gentle is impressed that Izuku knows of the Golden Tips Imperial tea, and Izuku admits that a friend served some to their class. Izuku finds the disguised man's voice familiar while Gentle praises Izuku's friend but soon deduces that Izuku is from U.A. Suddenly, Izuku manages to figure out his identity. Gentle sees that it is too late to cover up since Izuku is not naive, he turns around and takes his mask off asking who Izuku was referring to. Izuku tells Gentle that he saw his video; Gentle faces Izuku as he tells La Brava to turn the camera towards him. Izuku prepares himself and tells Gentle to leave U.A. alone.
Gentle praises Izuku for figuring out his identity while Izuku charges at Gentle but suddenly stops moving as he has run into an elastic sheet. Gentle reveals his Quirk's abilities. Gentle uses Gently Rebound on Izuku which blasts him across the street, as he comments on his dislike for using violence to solve his problems. Gentle and La Brava attempt to make their escape but Izuku comes charging at them. Gentle turns around and uses his Quirk on the ground. Izuku gets caught by Gentle's Gently Trampoline and is shot into the air. La Brava remembers that Izuku is from U.A's Sports Festival and tells Gentle this fact, which surprises Gentle who now wishes to not be further involved with Izuku and decides to quickly infiltrate U.A. Izuku charges Gentle and smashes him into a construction building.
Retreating from the construction site Gentle and La Brava discuss her quirk until they are interrupted by Izuku appearing above them. Charging at them with super speed, he manages to pin them both down on the ground. Looking at La Brava Gentle thanks her as she speaks of her love for him which grants him a power up to overthrow Izuku. As Gentle delivers an attack to Izuku, he's surprised to see Izuku unaffected.
Gentle's jacket is caught on a construction beam, hanging him in mid-air. Refusing to waver, he plans on going through with his infiltration. Gentle jumps into the air using an elastic trampoline, but Izuku charges at him, until he starts bouncing around Izuku at great speed by turning the construction beams around him into elastic. Gentle uses his Quirk and turns a crane's hook into elastic, planning to slingshot himself and La Brava out of the construction site. He does and the pair are flung in U.A.'s direction. Using his enhanced strength, Izuku fires a long range attack at Gentle and La Brava. Gentle dodges it and notes Izuku's tenacity.
When they are knocked back by Izuku's attack, Gentle refers to him as incorrigible. La Brava apologizes for her love not being enough but Gentle tells her nothing can prove that her feelings weren't enough. He attacks Izuku with a Gentle Sandwich claiming he must fulfill his fleeting dream. Revealing the more he tells him to give up the more determined he becomes. When he's asked why he must infiltrate the festival he says there's no other way for him to further his goals. As Izuku gets up he tries to throw him but is rebounded. They then proceed to clash with each other.
Izuku and Gentle clash with La Brava cheering Gentle on. Izuku is beginning to be overpowered by Gentle's enhanced strength which Izuku assumes to be the work of La Brava's Quirk. Gentle asks Izuku why he aspires to become a Hero. Izuku answers that just like Gentle his dream is no longer his and will achieve his dream for the sake of those who believed in him, wanting to be the man who shows everyone a brighter future. Izuku's response brings a smile to Gentle's face. As Gentle knocks back Izuku, La Brava takes the opportunity and brings out her computer and using special wireless technology plans to hack into U.A's internal network to disarm its security. However, she is out of range and tries to move closer.
Izuku sees this but Gentle plans on keeping Izuku occupied longer; Gentle jumps from his aerial elastic barrier and lunges into Izuku who manages to keep his guard up, mitigating the damage. Gentle creates several aerial elastic barriers and jumps from them all over the vicinity hitting Izuku and knocking him down. Gentle yells that he will discard his reputation and style of fighting to defeat Izuku, having developed respect for the boy. Meanwhile, La Brava has moved closer to U.A, but isn't able to proceed further as Hound Dog and several clones of Ectoplasm have caught a whiff of Izuku and Gentle's battle. On the ground, Izuku launches several wind pressure attacks which Gentle manages to evade most of but is hit by one of them. Gentle loses his balance and is stunned as a result of Izuku's air pressure attack. Using this opportunity, Izuku jumps in front of Gentle and attacks him with Shoot Style: St. Louis Smash. The strength of Izuku's St. Louis Smash is enough to finally bring down Gentle and render him immobile. Izuku apprehends Gentle and admits that out of all the battles he has fought, the one with him has been the toughest so far.
La Brava returns to Gentle and sees that he has been defeated by Izuku as Gentle orders her to run away. Devastated, a crying and flabbergasted La Brava demands Izuku to let Gentle go and while hitting Izuku, lamenting that Gentle poured his heart and soul into their U.A infiltration plan and that she is unable to live without him. Knowing that La Brava is fine with committing criminal acts as long as it's with him, Gentle realizes that if he allows La Brava to escape she will go on to committing an even worse crime. Blaming himself for La Brava's nature and knowing that she will be charged as being an accomplice, Gentle musters up the remaining strength given to him by La Brava's Quirk and pushes Izuku off and into the air, using his Quirk to bounce Izuku away. Gentle hugs La Brava as he tells Izuku to fly away for the sake of La Brava's bright future.
Hound Dog and the Ectoplasm clones find Gentle and La Brava, as Gentle declares his surrender. As he is interrogated by Hound Dog, Gentle downplays La Brava’s role in his crimes, and insists that he brainwashed her. When asked about his injuries, he claims he got them in a fall, and when confronted about Izuku’s scent on him, points Hound Dog in his direction. Some time late, during a police interview, Gentle continues to downplay La Brava’s involvement in his crimes, and explains his motivations to the officer.