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Baseball history is so amazing that there is probably no wrong era to play, and the best part is, your experience will be entirely different with each era and with every team you play! 1920s Red Sox will be much different from the 1940s or modern. Playing against the Yankees in their heyday can be a very challenging task. Seeing Ty Cobb playing a game in the deadball era is so much different from watching Babe Ruth scoring those home runs. Every era has its flavor and the whole set of teams that can be easy to play, almost impossible, or somewhere in between, but hey, if Amazin' Mets did it, so can you!
My favorite game so far was probably playing the Red Sox from the 1933 when Tom Yawkey bought the team and poured some cash in. Challenging those damn Yankees in a time when the Red Sox were doing really poorly was the challenge I needed, and I still remember the experience fondly.
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