I am bummed that Lester signed with the Cubs...not so much that he signed with them, but that the Red Sox ownership/GM made that horrendous offer to him back in Spring Training. I think that, to Lester, cemented his decision to leave.
I will say that while they're not "top of the rotation" people (like Lester proved he is/can be) I DO like the addition of the 3 Rotation arms the Sox made: Miley, Porcello and Masterson. I still hope they're looking for that #1 though (Shields or Hamels).
I do hope the Rockies eventually get new ownership (not likely)--as that is what I TRULY feel is holding them back. They get an ownership change, or the Owners decide to COMPLETELY cede Baseball operations to actual baseball people and not glad-handing "yes-men", then they will suffer for a season or two while they build their prospect base, but they'll pull out of it.
They can start by seriously shopping one of or both of Gonzalez and Tulo. Both of those guys can bring back some good pieces for the team to (hopefully) build off of.