For someone who is just a student (with a brand-new Quirk to boot), Izuku Midoriya has certainly had his fair share of fights against high-end villains, and surprisingly lives to tell the tale. Strangely enough, however, Deku's toughest battle is often overlooked.
Gentle Criminal and La Brava make a fleeting appearance in My Hero Academia, but, according to Deku, they are the strongest opponents he had ever faced. The trio has their big fight in Season 4, Episode 21, just before the UA School Festival is about to get underway (which is supposed to be dearest Eri's first big outing).
You've Been Struck By- A Smooth Criminal
Danjuro Tobita prefers to go by the more mysterious moniker, Gentle Criminal, which is quite an adept description of his underrated Quirk (and personality type, too.) As a passionate video content creator, Gentle Criminal ensures to a add dramatic, flamboyant flair to his attacks, and for a peace-lover, he is a surprisingly formidable combatant. Danjuro's Quirk projects elastic properties onto any inanimate object he touches, creating a significantly unstable landscape for his opponent to navigate through.
The highly-intelligent Gentle Criminal increases his mobility and speed substantially after bouncing off his carefully placed elastic air trampolines, which also double up as shields against an unsuspecting assailant. By creating multiple invisible barriers, Danjuro can entrap his foe in a "Gently Sandwich," granting him the perfect opportunity for escape. He seems to be fully aware of where all his stretchy traps are placed, so as best not to get caught up in his own transparent barriers.
The Power of Love
La Brava was once a sweet and innocent girl who went by the name Manami Aiba, but her world was turned on its head when she first laid eyes on Gentle Criminal. Determined to also follow a villainous path, one might wonder how Love could thwart her prospective enemies, however, even the great All For One would be blessed to have little La Brava on his team!
Manami's hacking talents are so on point that many first assume that it has something to do with her Quirk, but those are all learned skills! La Brava's special ability makes her the ultimate support character, as her Quirk immensely bolsters her beloved's power levels (so long as her love is true.) The greater the girl's affections are, the more substantial the boost, however, they would be ineffective if La Brava's affinity is questionable.
A Gentle Glow Up
True to his villain name, Danjuro is consistently a perfect gentleman, even in the middle of conflict, and he is always up for a spot of tea! Unlike Saiko Intelli, his tea-drinking obsession hold no greater value than adding some style and sophistication to his videos; and becomes a calling card of sorts to provide clues regarding his target's location. From a young age, Danjuro aspired to become a Hero but his lackluster performance at school sadly led him to be ostracized. Giving up on his dreams, the despondent young man tried his luck at villainy and technically got it right this time around (although it is unlikely that Shigaraki would agree!)
As the most flaccid, (oops!) placid villain in My Hero Academia, Gentle Criminal's new goal in life seems to have more to do with gaining subscribers that causing any great harm. Some of his greatest offenses include breaking and entering or obstructing justice (while ensuring to get it all on camera, of course!) La Brava makes the perfect sidekick with her passive Quirk and keen technological skills, and has been a huge help in editing and uploading copious amounts of video footage.
Deku's Toughest Opponents
The only reason why Gentle Criminal and La Brava pose any kind of threat during the School Festival Arc is because all of the Heroes have been on high alert since All Might's retirement. Villains have been crawling out of the woodwork and have started acting out, and even holding a festival in the first place is a massive risk. To quell concerns, Principle Nezu instated the rule that any suspicious disturbances would result in the event being shut down immediately, which would be a great disappointment for poor Eri. Gentle Criminal and La Brava had no idea the commotion they would cause, but knew that it would likely gain a lot of attention!
The duo of delinquents pulls out all the stops as they attempt to bypass Deku and step foot on the school grounds, and for a while, it seemed like they may just be successful. Deku is forced to reveal some epic moves of his own and eventually lands the winning blow with his St. Louis Smash. Following their exciting battle, Deku told Danjuro that he is officially the toughest opponent he has faced (so far), which is a grand statement to make considering he had recently fought against the potent power of Overhaul.
While gaining the upper hand over Gentle Criminal may have been a particularly tricky feat, many fans believe that Deku's main struggle was an emotional one (who's surprised?) or he was simply trying to boost Danjuro's ego out of pity. As an excessively empathetic young man, Deku often finds himself sympathizing with others, be it friend or foe, and he could completely relate to the rejection that Danjuro faced for most of his life. The bond between this Criminal and La Brava is so sweet and pure that everyone's heartstrings feel a massive tug during their teary separation, as this devoted make-shift little family is too adorable to pull apart. As a final act of love, Danjuro convinces the authorities that he brainwashed the young girl into being his accomplice in the hopes that she would receive a lighter sentence than him.
Season 6 of My Hero Academia is currently streaming on Crunchyroll.