This is still one of my most favourite scenes of Takasugi from the anime (it’s great in the manga, too). The lighting, the way his hair frames his face, his gaze…I’ve said this many times to the point where I even give myself secondhand embarrassment, but this man is beautiful.
There’s this frame in a flashback where Takasugi slides his hand over his heart while presently talking to Gintoki about avenging Shouyou. The specific quote is, “You could put an end to everything by piercing that chest with a sword.” I had originally assumed that Takasugi was referring to Gintoki, but an epiphany hit me during a random rewatch of episode 305.
Unlike us, Gintoki doesn’t get to see the scene of Takasugi alone at the bow of his ship. It’s almost too easy to take Takasugi’s statement at face value (get revenge for sensei by taking the life of his executioner in exchange), but that flashback is actually a privilege and subtle clue to us viewers. Takasugi is suicidal over Shouyou’s murder. In his most raw and unguarded moment, Takasugi is actually confessing to Gintoki his rock bottom thoughts: It makes more sense to take his own life because they deserved to die that one day as their sensei was the one who truly deserved to live.
But Gintoki doesn’t flinch at this revelation, like he has always been aware of the darkness Takasugi has been carrying ever since. Even after all these estranged years, Gintoki has kept Takasugi in the back of his mind. Though, Gintoki disagrees at the notion of Shoka Sonjuku dying alongside Shouyou. Shoka Sonjuku lives on through them, as the remaining disciples. Gintoki has willingly allowed himself to be the focus of Takasugi’s hatred. …Perhaps in the hopes that somehow he can keep Takasugi from completely sullying himself and in turn keeping the soul of Shoka Sonjuku alive.
In the end, Takasugi is amazed that despite his all-consuming faithlessness, Gintoki and sensei still accept him. Remember, Shouyou himself once told a little Shinsuke that it’s alright to lose your way in order to find your own definition of being a samurai.