User blog comment:Flamesword300/KANEME'S DEAD FRIEND/@comment-1429792-20091210232908

No. Miyako Shiba was killed before Kaien was possessed by the Hollow. And this was less than 40 years before the current timeline. Tosen, who joined the Shinigami because of his friends death, was a Shinigami over 100 years before the current timeline