I noticed something interesting about the eight managers that made it to the post-season. Half of them are ex-Cubs. No other team could claim more than two, but the Cubs once had four of them.
Of the four, Joe Girardi would be the one most identified as a Cub. He was drafted by the Cubs in 1986, and made his MLB debut with them in 1989. He was selected by the Rockies in the 1993 expansion draft and spent time in Denver and with the Yankees, before returning to the Cubs for three more seasons (2000 - 2002). He played more games in a Cubs uniform than with any other team.
The other Cubs product is Jim Tracy. In fact, he played only for the Cubs in his brief, relatively unproductive two year big league career. He would have been one of the last former Cubs I would have ever figured to become a manager.
Terry Francona spent the 1985 season with the Cubs as a part time outfielder.
The final ex Cub is Tony LaRussa. He also had the briefest tenure with the Cubs of the four managers, one game. Tony made the Cubs roster coming out of spring training in 1973. He made his only appearance for the Cubs, on April 6, Opening Day. He pinch ran for Ron Santo in the bottom of the ninth inning and would eventually come around and score the winning run as the Cubs beat the Expos 3-2. On April 17 he was outrighted to Wichita and would never appear in a major league game again.
Pictures on him in a Cubs uniform are pretty tough to come by. Topps didn't issue a Cubs card of him (his last as an active player was with the Braves in 1972) I spent a while poking around several different websites and couldn't find one Cubs picture of him. Anyone out there got one to share??