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You can't force or even encourage a pitcher to learn a new pitch. It's random. Assume that all pitchers are trying out new pitches as they go, but only a few manage to develop one that is good enough to use in real games effectively.
Pitchers whose pitch ratings are exceptionally low may give up on their pitches.
Pitchers are slightly more likely to gain a bit stamina than a third pitch, so if you have to choose between a player with three pitches and somewhat low stamina or a player with two pitches and good stamina, I'd go with the former.
If a player's projected role in his current league is "Bullpen", I wouldn't even think of using him as a starter. It usually won't go well. "Borderline Starters", sure, can sometimes work out.
Not everyone can be a good starting pitcher. Lots of good relievers in real life can't cut it as starting pitchers. This is the mechanism used to reflect that.
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