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Brian H (misunderestimated)I though I would approach this somewhat chronologically (giving each decade & the Negro Leaguers a representative). The loosers in this game are basically the second best players of any decade or two (Joe Jackson, Tris Speaker, Lou Gehrig, DiMaggio),and long career players whose greatness is based on 15-25 yrs of excellence such as Cap Anson or Pete Rose. I did try to credit power and On Base percentage rather than simply batting average (hence Frank Thomas' inclusion over Griffey and Delehanty over Keeler):
Dan Brouthers
E.J. Delahanty
Honus Wagner
Ty Cobb
Babe Ruth
Rogers Hornsby
Oscar Chaleston
Stan Musial
Ted Williams
Josh Gibson
Mickey Mantle
Willie Mays
Hank Aaron
Frank Thomas
Barry Bonds
Also, how did Bill James fail the Red Sox ? You must know something I don't. More or less when he became involved (presumably at Theo Epstein's urging) they won their first World Series in ... (well we all know the story)