This has always puzzled me too, especially since they got Johnny Damon, who has wings on his heels.
Any time and every time Damon is on first base, he should get more attention from the opposing pitcher than the guy at the plate does. Even if he's not going to run, he should be grimacing and doing a "I'm gonna run, watch out, boy, I'm gonna run" dance to drive the pitcher berserk.
Remember Kenny Lofton in the mid 90's?