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Kurama said:*Spoilers past the Chapter involving Isshin and his dirty little secret. 180, I think*
Isshin could've been a decendant of the Shiba family, abandoning the Shinigami and tossing the name into disgrace. He could've fled to the human world and met up with an old friend (Urahara), meeting Masaki (who could've been Kurosaki already, in Japan they sometimes take the wife's name), falling in love, and then asking Urahara to make him a special Gigai. Thus, Ichigo could be both a relative of the Shiba family AND the reincarnation of Kaien.
Kurama said:Well, I meant that Urahara had already left, and Isshin stayed behind. Then when Isshin finally does leave (yeah, likely for Masaki), he remembers Urahara, and meets up with him.
Of course, it could all just be Kubo Tite being an ass and having nothing to do with anything.