Cherington addressed their needs: OF, 1B, and starting pitcher. They all have reasonable talent and Cherington did it without giving up top minor league prospects and long term contracts.You may have wanted other players to fill those needs but they were just about the best available. I'd give hm a B.
I'm surprised that the Yankees didn't go after a SS instead of Youkalis. Jeter lost range before his injury and next season would have been the right time to move him to 3B. Arod may never be back and Youkalis won't make it a full season at 3B. I guess the Yankees could always do that if they had to but I'd want Jeter adjusting to playing 3B from the start of Spring training.
Toronto spent some money and got better but you are right, the big money and talent went west.
I guess it depends on what Cherington was told to do. If he was told that to make the Red Sox a contender, IMO he failed, at least so far. If he was told to keep the salaries down and wait for the prospects to come on the scene then I too would give him a B. If the Sox want to contend, they need a shortstop, a catcher, a top of the rotation starter and a legitimate first baseman. Iglesias is unlikely to hit enough and the rest of the lineup cannot afford an automatic out. If they had signed Hamilton, they might have been able to get away with Iglesias' bat. Of the catchers, the best of the lot is Ross but he cannot play full time. Salty is a strike out machine who is not good with the pitchers. Hard to say what we'll get with Victorino. Last year he hit .255 with 11 home runs. That is not a lot of production for $39 over three years. He can steal bases but will anyone be able to knock him in? Mike Napoli, assuming we can sign him, gives us a poor fielding first baseman with power. Although he can catch too which gives us some flexibility, he is not good there either and he is injury prone. Ryan Dempster will turn 36 in May and may be at the tail end of a fairly descent career. It remains to be seen if he can be effective in the American League.
If I were Ben, I would go hard after Felix Hernandez. I would offer Lester, Salty, Ellsbury and I would throw in Barnes if necessary. As I said in an earlier post, both Lester and Ellsbury are from the Pacific Northwest and the change might be good for them. The Mariners need help at catcher and although Salty might not be the best solution for them he is better offensively than their current catcher. Barnes is a legitimate prospect who could help them down the road. With King Felix at the top of the Red Sox rotation, the Sox are a contender. I would put Victorino in center and split the catching duties between Ross and Lavarnway. I would give Iglesias three months to see if he could hit enough. If not I would bring Bogaerts up and see what he could do. King Felix would excite the fan base and that is sorely needed in Boston.