1) Had the Sox offered Lester five years at 110M a year ago he would still be on the Red Sox.
2) The Cubs overpaid. Chances are they get three or four top of the staff years from Lester before he fades into a back of the staff pitcher.
3) The Sox fooled themselves with a pennant in 2013. Even when things went wrong (example: two closers injured) they went right (Uehara). In 2014 everything went wrong. I have a wait and see attitude on Ramirez and Sandoval (in the long run). I've seen two desirable pitchers in Lester and Smardzija slip away. They were outbid on Miller. Other teams are looking for pitching too.
RJM,
1) Exactly. Front office screwed the pooch. Lucchinorized.
2) Yes they did for 6 years/$155M. The sixth year is the tough part to swallow but the Sox could have got him for 5 years if they had a clue in how to negotiate (before his walk year) which clearly they don't.. 5 years would have been palatable.
3) Agreed. 2013 was a World Series title despite the Front Office's arrogance. They didn't realize how lucky they were.
I hate to say it but the Red Sox are beginning to resemble the dysfunctional NY Yankee front office of yesteryear (Steinbrenner years). It is very disturbing.