I can't guarantee this will work, but if you can find your SOM baseball folder and look under Support > Tech, you'll see a file called vcredist_x86. You should run that. It's a common fix for the football game, not so much for the baseball game-- but it won't hurt to try. Another common problem is that anti-virus programs don't seem to like Strat-o-matic games very much, even though they are harmless of course.
Incidentally, this forum is actually for the online version of Strat, called Baseball 365. You should check it out! No download required, and there's a free trial so you can decide if you like it or not.
https://365.strat-o-matic.com/help/rules/baseball