In 2005, Takahashi is a lieutenant of the Shimano Family. He is sent by his boss to try to coerce protection payments out of Stardust, a host club in Kamurocho that has been functioning without paying protection thanks to permission granted by the Kazama Family.
When Takahashi arrives at Stardust to try to extort them, he is refused by the club's manager and bouncer, Yuya. Takahashi causes a commotion that is heard by the club's owner, Kazuki, and his guest at the time, Kazuma Kiryu. When the argument between Takahashi and Yuya escalates, one of the lieutenant's goons tries to attack the host with a champagne bottle, only for Kiryu to stop him with a punch to the face. A fight breaks out and Kiryu and the Stardust hosts manage to drive the Shimano goons away without paying them.
Later on, a heavily bruised Takahashi reports the incident to Shimano while he is preparing to attend Chairman Masaru Sera's funeral. Based on the description provided by Takahashi, Shimano correctly determines Kiryu was the one who aided the Stardust hosts. Shimano then thanks Takashi for the information before cutting off one of his fingers for failing to get the protection money.