Oboro
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Oboro is the current leader of the Tensho School and the strongest assassin within the Naraku organisation. Trained in the Tensho school and later succeeding the previous generation's head position. He once fought against Sakata Gintoki during the Amanto War, but wasn't able to kill him. It is heavily implied that he was under Tokugawa Sadasada orders to kill the remaining Joui Patriots. Oboro also has extensive knowledge about Yoshida Shouyou and Gintoki's past. He refers to Gintoki as a demon who howls at Heavens.
