I heard there is a festival...
I couldn't help myself, so I came.

all that was his doing.       The first time Takasugi is introduced is during the Gengai Arc, where Takasugi manages to cause a commotion during a festival with the aid of the town's mechanic, 平賀源外 (Hiraga Gengai). Gengai's son had left some years ago to fight against the Amanto in a small-scale volunteer group that Takasugi had led. Upon learning of his son's death, Gengai completely immerses himself in his robotics, closing himself off from the world around him even further. It's during this arc that we see Takasugi's innate ability to manipulate people. It's also here that we learn of Gintoki's and Katsura's past lives. Of course, Takasugi's plan flops: he underestimated Gintoki, but no matter. He'll just try again next time, and try again he does.

save for
a rainy day

comrades? please.       The 紅桜 (Benizakura) arc begins with the assassination of Katsura, prompting his faithful pet Elizabeth to seek out the Yorozuya to help find him. While being commissioned on the side by two swordsmiths, Gintoki searches for a powerful living sword. Long story short, Takasugi is the master-mind behind these turns of events, but is not entirely responsible for the attack on Katsura. Instead, it is his subordinate 岡田似蔵 (Okada Nizou) who takes the benizakura sword and singles out Takasugi's old comrades in the area. Takasugi's initial plan was to overthrow the Bakufu with a military coup using an army of these specialized swords. Takasugi would have been successful, had it not been for Katsura and his infiltration of the ship. It's come to the conclusion that Takasugi has grown tired of his old comrades; he wants them gone and out of his way. And of course, what better way to do this than offer Gintoki's and Katsura's heads to the Harusame Space Pirates?

      Enraged by this, Katsura and Gintoki swear that next time they meet Takasugi, they'll cut him down for good. Takasugi no longer sees his old friends as his comrades; something happened to their relationship either during or after the war. Whether this was a trait he had all along or something that came to be after his teacher's death, Takasugi is the type of person who never actually cares for his subordinates. They are nothing but tools at his disposal, ready to be replaced at any given time. Takasugi treats both Gintoki and Katsura in the same light: he uses them as his ticket into the Harusame, completely severing the smallest attachment he could have harbored towards the two.

We started off in the same place. Now... we're worlds apart.

(Katsura, chapter 97)

you can't keep
up with my music?

      By using a Shinsengumi advisor named 伊東鴨太郎 (Itou Kamotarou), Takasugi planned to create a large crisis within the Shinsengumi, setting it up so that the organization falls apart from the inside. With Bansai as an additional destructive force, Takasugi was successful in creating a bout of riots within the ranks, but fall short after the interference of Gintoki. When Bansai returns, he gets a verbal beat down from Takasugi himself, but flatlines after Bansai questions if Takasugi understood what Gintoki protects. While Takasugi had no physically active part during this arc, he was, once again, the one pulling the strings.