I have to disagree with the idea that trading Lackey for Kelly and Craig was bad at the time that it happened. It looks bad as of this moment, but it wasn't a bad trade going in, and it might end up not being a bad trade in the end.
1. Ben was looking for major league ready players, not prospects. With both the Lester and Lackey trades, he wanted players that could help the team contend this year.
2. Too many people are looking at only the short term (this year) in this deal. Kelly is a cost-controlled player until 2018 and Craig is under contract until 2017, with an option for 2018. The deal was made not only with 2015 in mind, but also for the longer term.
3. Kelly was a 26 year old pitcher who can hit 97 mph. He has some upside, and he is cheap. He pitched fairly well with the Cardinals.
4. At the time of the trade, our outfield was a mess. We did not have Castillo. Victorino's health is always a concern. Betts had all of 10 games under his belt and wasn't hitting that well in that small sample. JBJ couldn't hit his way out of a paper bag. Sizemore was gone. Hanley wasn't signed yet. Holt was cooling off. The Sox needed some outfield depth. Craig was not just an excessive piece. And the fact that he can play 1B didn't hurt.
5. Before his injury, Craig was a very good hitter. He is not that old. It is not unrealistic to think that if he got healthy, he could rebound to close to what he was in 2012 or 2013. If he did rebound, his contract would be considered cheap.
6. The Sox have taken fliers on players like Craig before. Victorino, who played very well in 2013. Stephen Drew. Beltre. They worked out.
Yes, the trade looks bad right now, but the rationale in making the trade at the time is very sound.