Would Derek Lee have been able to get more money (I know he's not all about the $$) if he hadn't signed his contract prior to his injury?  Do you think this would have driven home the point to the Cubs brass at how truly valuable he is and Lee's agent could have used this to their advantage?  

I do.  I think if that contract was not signed when it was and the injury occured and assuming he came back and had a productive remainder of the year, it would have either caused him to seek free agency or he would have earned significantly more than what he had signed for.

I understand it's a moot point but in my opinion the Cubs lucked out by locking him up prior to his injury.