If anything, I think it becomes more important to move Morneau, Willingham and Span. Willingham and Span are excellent players, but the truth is that our dearth of starting pitching extends throughout the minor league system; whereas our outfield depth is quite a bit stronger. Already in New Britian, we have Aaron Hicks, Oswaldo Arcia, Joe Benson and Rene Tosoni as interesting (but flawed) OF prospects.
Now, if we could get more for, say, Hicks, Arcia, Revere or Benson than Willingham or Span, I'd be all for it. I think we all know that's not possible, and something in the OF has to give because there's a blatant OF jog jam on the horizon.
To me, ultimately, the point is to win a championship--not to get good enough for a long string of first round exits again. To do that, we need to be strong all over the board. The way to do that from my perspective is to balance resources to create a perfect storm. Simply signing a pretty solid starter and creating a huge OF traffic jam in the minor league system while relying on Diamond, Gibson, Hendriks, Wimmers and Bromberg to make the rotation title-worthy just seems unlikely.
Now, if Span and Willingham could net two high-end starting prospects, I'd feel a lot stronger about getting that starting rotation where it needs to be and shooting for Revere to replace Span's production and for one of Benson/Hicks/Arcia to step up and replace Willingham isn't completely outlandish.
Move Morneau, and use all of our newly freed up money to sign a top-end pitcher ace. Then, throw in Diamond, Gibson, Hendriks, Wimmers, Bromberg and two top-end pitching prospects acquired via trade to make the rotation come together.
Roll with Revere, Hicks, Benson, Arcia, Tosoni in the outfield. Bank on Plouffe, Dozier, Rosario, Sano and others in the infield (Michael, Santana, Beresford, etc.). Throw in Waldrop, Guerra, Gutierrez, Oliveros, Slama, Robertson and a few others in the mix in the bullpen, and all of the sudden 2014 looks really interesting. If Rosario and Sano aren't ready yet, we definitely have enough money to fill-in their positions with solid vets on short-terms contracts.
To me, this makes a lot more sense than keeping Wilingham and Span around, and we don't have to wait until 2018 to be great.