I would guess one of the tough ones would be Tommy Lasorda, who I remember from an interview he managed when Lasorda was pitching. I know for sure you'd have Ted Williams, Enos Slaughter, Ernie Banks, Ron Santo, Larry Doby, Billy Williams, Bob Feller, Satchel Paige, Bob Lemon, Joe Gordon, and George Kell. Then himself as he was a player/manager for the Indians. That'd be 12. My great-grandma was a huge Cubs fan, and I remember her talking about the year that he managed the Cubs. They had Don Zimmer, who should be a HOF guy eventually, but he's not in yet.