Masashi Toogaito (遠垣内 将司 Tōgaito Masashi) is a third-year student of the Kamiyama High School and a president of the school's Wall Newspaper Club.
Masashi is the son of the Toogaitō family, well-respected and influential members of the educational community. He is the President of the Newspaper Club.
As an upperclassman to the main characters, Masashi acts mature and composed. He has proven to be a cautious individual, careful to keep his secrets and even resorts to lying to do so. It seems that Masashi is very wary of his family's reputation and is careful to not tarnish it. On the other hand, he uses the reputation of his family to disobey school rules, particularly smoking while inside school premises, with impunity.
Masashi is shown to be slightly taller than Houtarou. He has umber-brown hair that reaches past his chin. Masashi also has periwinkle eyes. Aside from his Kamiyama High School uniform he wears neutral colored clothing.
Masashi is introduced when Houtarou and the others are looking for the past anthologies of the Classics Club located in the Biology Prep Room, which was used by the Classics Club before the Newspaper Club moved in. Because of his smoking activity inside the Biology Prep Room, Masashi refuses to let the club search for their anthologies inside. It is later revealed that Masashi is an underaged smoker who hid his cigarettes in the same safe as the anthologies. Houtarou later uses this knowledge to blackmail Misashi to deliver the club's anthologies. As a result, Masashi has become cautious of Houtarou ever since.
During the Kamiyama High School Festival, Masashi clashes once more with the Classics Club in the middle of the Juumonji Incident. To gain readers for their next publication, the Newspaper Club followed the events in the Juumonji Incident and even challenged the culprit to show up, as if competing against the Classics Club. Neither side truly won in the case, although it is partly due to Houtarou handling the case from behind the scenes.
Mashashi is among the three who told Fuyumi about Houtarou's abilities.