Tsuna and his friends are now on Year 2 and Tsuna is checking the board to find out which class he is in for that year. He doesn't see his name in class A, class B and class C, making him think that he needs to redo a grade. He suddenly notices the name of "Naito Longchamp" ostensibly decorated, in the column of Class A. Tsuna removes the decoration and see that his name was hidden under it. He also sees that Gokudera, Yamamoto and Kyoko are in the same class too.
As he wonders who Longchamp is, he realizes that he is right behind him with three other people throwing him to the air to celebrate him becoming second year. Longchamp then approaches Tsuna and introduces himself as the eight boss of the Tomaso Famiglia. Tsuna tries to pretend to not know anything but Longchamp ignores him and introduces him to the three people which are members of his family. Longchamp asks Tsuna to introduce his family to him when Gokudera and Yamamoto arrive. Longchamp introduces himself to them and Gokudera informs Tsuna about a large skirmish between the Vongola Famiglia and the Tomaso Famiglia during the second generation, causing Tsuna to realize that Longchamp is really connected to the Mafia. The group then heads to class.
As Tsuna talks to Kyoko and Hana. Reborn arrives as the substitute teacher, Reboyama, informing the class that their teacher is absent. He decides to start the nominations for class president. Mangusta immediately nominates Longchamp followed by Gokudera nominating Tsuna. Reborn tells the two to show their skill and Longchamp sees it as a bragging contest and begins to tell the class his failures in life. When the class gets irritated by him, Longchamp decides to introduce them to his girlfriend who enters and leaves immediately. Gokudera then begins to tell everyone about Tsuna's home tutor and Naito also reveals that he's being tutored by Mangusta too. The class starts to decide to vote for Tsuna, causing Mangusta to shoot Longchamp with his Desolation Bullet. The bullet causes Longchamp to get the sympathy of his classmates and causes him to be elected as Class President.
Note: Bold + Italicized = First Appearance