(This is for the fanfiction "Crossover Together". Info may change from canon information)
Gakuho Asano is the principal and top mind behind Orora High School.
He has neatly combed brown hair and violet eyes. Asano wears a formal business suit that is unique from the other staff members in Kunugigaoka, as it's brown instead of the usual grey or black. He also wears a sawtooth leaf pin on his tie that was given to him as a present from his cram students.
He is noted to be a shrewd administrator who made Orora High School the best in the nation within the 10 years since its founding. He was the one who created the Class E system, under the thought that having someone to discriminate makes one progress further. His aim was to create "stronger" students in both mind and power with this method.
His obsession with education gives him an abnormal sense of prioritization, as he prioritizes the maintenance of his educational ideals above all else. The maintenance of his school and system is his primary driving force. An example of this is when he decides to put Nagisa Shiota (a hero for defeating Pluton) into A class so people wouldn't shame the school for their poor treatment on him. This also makes him move towards decisions that question his basic morality, such as him deliberately letting E class go on a field trip to Elysium without informing them of an important test to be sure they don't pass, and earlier when he allowed Akira Tataoka to take charge over class E to make sure they stay the lowest rank, in spite knowing of Tataoka's cruelty.
When Heine Wittgenstein is hired into his school, Heine's actions began to put more pressure on Gakuho, and he became more desperate to keep his system in tact. As he failed more and more times against him, he got to the point that murdering Heine would be his only option, putting other students' lives in danger to do so. It wasn't until after being stopped here (and hearing of Ciel Phantomhive's torture compared to his own) that he began to see the error of his ways.
He didn't try to encourage the students and staff to look down onto the E class any further since this incident, and tried to treat all classes more fairly from then on. This though was more of him being worried that his school could be shut down altogether because of this.
In the past, Gakuho Asano was a more level-headed man, who taught his students at the main building, A through E, to be kind and well-rounded. He was close friends with one student, Rikuto Ikeda, who he admitted was a son he wish he had. One day, Gakuho couldn't find him, and went to look for him, just to find that he committed suicide by jumping off of the cliffside south of the 3-E building.
After finding out the culprits, He would later use his brainwashing techniques to turn his student's bullies into desperate gambling addicts as revenge. The memory poisoned him, and he saw it out to make his students "strong" instead of "good", as he thought that was the reason he couldn't do anything for himself.
After hearing rumors of Demons roaming near his school, he decided to call Nagisa Shiota to his office as he suspected he would have some connection with them, along with the sudden spike in good grades by the E class. Using footage of Blair inside Nagisa's locker as a bribery, he promised to remove the incident off of his record in exchange for Nagisa to spy on the E class to see what was going on, as Gakuho chose him for his observant and quiet behavior.
When Nagisa returned, Gakuho was disappointed to find that Korosensei had found him first, and he requested for him to try again, just for Karma Akabane to come in and volunteer for him. Suspicious, Gakuho had Karma placed in E class, something he seemingly wanted to do on his own terms rather than his.
In the final exams, he deliberately made the questions extremely difficult, some questions not even having a correct answer to them. On Nagisa's test, he wrote in "clever" on his report, as he was one of the few to see the catch.
Gakuho was confronted by Niji sometime after he put Akira Tataoka in charge of the E class, being asked if he was going to do anything about the class's situation. Gakuho though made it clear that it was intentional for a brutal instructor to be placed there, and that it shouldn't concern her as she wasn't even in his school. Despite believing nothing horrid would happen, Gakuho went to check on the E class anyway, just to find Tataoka "killing" Niji. This over-stepped the boundaries he had placed, and he promptly fired Tataoka sometime later.
Gakuho welcomed Team Harmony back upon their return, hearing of their efforts with the Pluton incident sometime prior. He was contacted by one of his staff, as a new instructor, Heine, wanted to take part in his school. He got him through a competence test, but also suggested that he checked on him to be sure he didn't make the same mistake as with Tataoka.
He started to sense his system weakening as time went by thanks to Heine's involvement: moving E class to the main building, and the improving grades on top of it all. He tried numerous methods to keep his system in tact (starting a test while class E was on a field trip, moving Ciel Phantomhive to Class A, and giving Heine a personalized, extremely difficult competence test), but all of his attempts didn't work. This drove Gakuho off the edge, and he got a pistol with mind to kill Heine to be sure his system didn't fall apart on him. Team Harmony tried to stop him, but he threatened their lives just as well. When Ciel Phantomhive arrived and asked for his reasoning, he revealed the true origin of his ideals, just to hear the horrifying past of Ciel.
After his "episode", he found Heine once again and promised that he'll try to treat all classes fairly from then on.
Gakuho briefly appeared when he was confronted by Hiromi Shiota, in hopes of getting Nagisa transferred. When he heard that hiromi won't let Nagisa have a say in it, he promptly refused, saying the students' opinion mattered as much as hers.
He's seen during the graduation, giving diplomas to the passing students, including Nagisa, with a smile on his face.