It would be nice, but not sure how feasible. You would likely have to be limited to following the real season's schedule (meaning it would limit you as far as playing ahead) in order to not mess it up.
Maybe some sort of pop-up for backfitting like "The Rangers have aquired Ken Griffey Jr through FA on 4/15/2009. Would you care to backtrack this transaction?" If you choose yes, regardless of the timeframe, it could make the move and attach him to that team for that specific period.
That might work. Getting into retirements and stuff could maybe make that much more complicated, plus stats would liekly not travel well this way. It's an awesome idea in theory, just not sure how they'd make it function. Plus, it's something that is likely sceaming for bugs to occur, unfortunately.

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