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In your league's main menu, click "League Setup" from the bottom right of the drop-down menu. Once you're on the League Setup screen, you should see various tabs. Click the one called Player and Picture Options. In the top right, you can tell the game whether to create player pictures, when it does it, whether it should update pictures when needed, etc.
Also, there are mass functions available on the Player and Picture Options. There is a button for "Update / Generate All Player Pictures". You can use this to update all of your players so that they have pictures. Just be aware that this may take a lot of time, particularly if you have a really large baseball world.
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