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No doubt this happens often in OOTP. i don't think OOTP has anything coded in to consider milestones and records when a player is thinking about retirement.
i kinda' prefer it that they don't drag out their careers chasing milestones and records. But i know a lot of people hate that and want to see the guys reach 300 wins or 3000 hits or whatever. Maybe it can be fixed in v2007.
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