Using this tool:
Using the 1959-2004 model I came up with this:
As the best possible lineup using their obp/slg coming into today. This is of course a flawed way of doing it since Young, Laroche, and DeWitt all have such small sample sizes.
I wonder if Torre would do something as crazy and non traditional as this lineup. Martin has the best OBP on the team which makes him the best candidate to hit leadoff...
Obviously there is no way Torre would ever bat Kent 8th.