Fun Question....
To talk baseball with - I'm a history buff -- I guess JJ McGraw or John M. Ward -- both knew the game really well and would be articulate and able to go way back... Contemporary I'm thinking Joel Maddon (but he admittedly never made the majors as a player) or maybe Billy Beane.
To just shoot the breeze I'm thinking about who is nice, interesting and intelligent so probably I'd stick with Maddon, Buck O'Neill or (to go waaay back Orator O'Rourke or Mathewson)
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Other People who I thought about were Branch Rickey (who barely played) and Bart Giamatti (ap) (who never played but I think it would be really interesting and was supposed to be a really good guy)... Also thought of non-players Theo Epstein and Bill James - which could happen, I guess.
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