What difficulty level are you playing on? In Rookie and Veteran, you can keep hitting the steal button and he'll take off as soon as the pitcher goes into his motion.... on All Star level you have to wait to press the button at the right time yourself or you'll get picked off/caught in a run-down. I usually lead off the maximum amount, then as soon as I see the pitcher's leg go up, hit the run button.... sometimes I make it, sometimes I don't... all depends on who's running.
I use the cursor... typically in an at bat I'll angle my cursor first, then lead off, then move my cursor around in the box until he starts his delivery. That's when I'll hit the steal base button, get back to the hitting controls, and take my swing. I don't know why, but I hit alot better when I'm moving the cursor in a circle around the strike zone... sometimes I'm close to the pitch, sometimes I end up in the complete opposite place where I should be... it's like a hitting trigger to me. Like the way Sheffield waggles the bat before he swings.
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