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You're not going to be able to make anybody enter and leave as they did in real life because that's not what OOTP does. OOTP is primarily a fictional baseball simulator and secondarily a historical career simulator, meaning that the game uses real life players as a starting point but throws in a lot of unpredictability. Ty Cobb could, for example, suffer a career-ending injury his first season in the bigs and end with 40 hits rather than 4,000.
You should, if the game is anything like past versions, be able to import players and rookies from year to year and then add individual players on top of that. I think one of the modified Lahman databases has Negro Leaguers included, but don't quote me on that.
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Clutch ability and veteran leadership are two of the most important intangibles that it takes to win.
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