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Retire players according to history
According to the manual, if this option is checked
"Forces players to retire from OOTP after the same season in which they retired in real life. Otherwise, OOTP will decide retirement by itself, and historical players may end up having significantly longer or shorter careers than they did in real life."
I started a league in 1959, checked this option and now am in 1960. I have many players still in the OOTP game whose last year in the majors was 1959 and are still active. In fact some are doing quite well.
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