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If you're using the unpatched MLB quickstart, Schilling may be still listed as Retired in his settings. Maybe even if you are using the updated version...
Anyways...
Go into Commish mode, then find Schilling. Go to his profile page and you'll see the Editor tab towards the top right. Somewhere on the left side of the screen under Basic or Team Information, there may be something saying he is retired. If there isn't, just reset his team information and whatnot, see if that helps.
Edit - Francisco Liriano, for example, had the same problem in MLB roster file.
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