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Beginning of preseason, assuming an expansion by only two teams. Usually there are still a few decent free agents left for the expansion teams. It depends on how good you want the expansion teams to be in their first season, though. Unless you do some additional editing of their finances, expansion teams in OOTP always have a TON of money and budget room, so if you expand early in the offseason they will snap up a lot of the good free agents, in my experience.
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"Sometimes, this is like going to a grocery store. You’ve got a list until you get to the check-out stand. And then you start reading People magazine, and all this other [stuff] ends up in the basket."
-Sandy Alderson on the MLB offseason
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