1. I would have re-signed Lester - not because I expected him to be a 5-win pitcher, but because I didn't have to worry about him. And I have more faith in his decline being a bunny slope more than a double black diamond.
2. The only other starter who would have moved the needle is Scherzer - but age an issue there too and I am not sure his stuff would have aged as well as Lester's - just my own thoughts. Shields is a fly ball pitcher who has pitched in great pitching environments his whole career - aside from durability (which is important) he was not worth stretching out on.
3. Cole Hamels and Yovani Gallardo were the only two proven starters on the trade market in the offseason. Making a run at Gallardo made sense - but he is not worth "Tier 1" prospects. Hamels has been the subject of many gigabytes of board discussion - no need to add more. Other guys interest me too, like Johnny Cueto - but the Reds had a genuinely decent chance of being, well, decent. It is hard to sell your fans on a fire sale when the team is actually not terrible. Mat Latos interested me too - but from early evidence, I was wrong there.
4. I think the guys the Sox dealt for were largely solid choices - innings eaters young enough to dream more of, and with a good defense, perhaps some reachable upside. Note, my goal was not to replicate the 71 Orioles or the late 90s Atlanta Braves. It was to deliver a rotation which could do its job enough to keep the team around while the teams around them figure out if they are buyers or sellers.