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I feel that steeling is much easier if you play historical since many pitchers especially of the 1980s and 1990s have really bad "hold" ratings in the game. I did experience similar things with historical starts (Kenny Lofton once topped 140 SB for a single season in a 1995 replay for me), but I never witnessed anything like that playing the 2016 quickstart.
Since it does seem to work as intended in modern games, I guess it should rather be an issue with historical pitcher ratings than with game mechanics.
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