This thread could also ask the question, "what players did managers choose to hit in the middle of a potent lineup when they didn't belong there".

You put Tony Womack clean-up for the 2004 Red Sox and I'd bet he'd make a run at 100...he probably sucks badly enough to miss but I'd bet he could make a run at it.
Of course, managers only put crappy power-hitters in the cleanup slot so that would never happen with Womack. That list Tavish posted are some shining examples of contact futility in the heart of the order though.
