I have been looking at this thread since it appeared and there are too many choices so I will categorize... Forgive me in advance.
Negro League ... Buck O'Neill
Pioneer .... Cap Anson
Manager.... Casey Stengel
Pre WW 2 player ....Ty Cobb
Post WW 2 player ...Stan Musial
Modern post 1980 ... Ichiro
Umpire ....Doug Harvey
Each era reflects not just baseball but also America , and most players and umpires are good storytellers. One of my favorites was Warren Spahn , but I did not include him since I spent a lot of time with him . Mickey Mantle could tell great stories but would really only open up around people he was comfortable with , he was very guarded .
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