I agree with you on AGon. I think he is someone Theo really wanted and was willing to give the big contract to. I think Crawford and Lackey were lapses, at a time where they fed into the "monster". They made those signings against their better judgment.
As far as Lester goes, I really think they screwed that initial offer up big time. Had they made that same initial mistake 5 years ago, and had Lester hit FA 5 years ago where some other team outbid the Sox by $20 mil, I don't think the Sox would have upped their price. They would have let him walk.
It's the same with guys like Damon and Bay. The Sox wanted them back, but on their own terms, not on the player's terms.