How many real life managers have asked this over the years?
If OOTP wants to simulate real life it has to have players making stupid mistakes.
What is his "baserunning" rating? Without looking to the manual I think that is the skill that determines a player's awareness on the base paths(taking an extra base or knowing when not to etc.) including being aware of pick offs.
Maybe intelligence is also used as a small part of the equation?
In any case it's very frustrating whether in real life or OOTP, I've had it happen too. In both cased all I can think is "how did you let that happen?"