Yankees- Johnny Damon- Damon was originally signed to be a centerfielder and its dissapointing he can't handle that position anymore. However, he's become one of the best defensive left-fielders in baseball. He does have a pitifully awful arm. However, his range is very good for a leftfielder. His bat has also showed little signs of decline. His EQA last year was the best in his career and its really surprising to see a guy who almost quit a couple years ago to still be playing as well as he does. Next year is his contract year and he's a Boras client. With a good year, you need to seriously consider re-signing the (then) 35 year old Damon.
Red Sox- Jason Bay- Its almost a relief to not have to type Manny Ramirez's name here. Almost but not quite. Unfortunately, they replaced him with a younger, cheaper and, at this point, close to equivalent player. Bay is clearly not a good fielder. Over the past two years, he's cost his team over 30 runs according to UZR. However, like his predecessor, he can hit. Aside from his awful 2007 he has consistently put up great numbers. He's also shown he can handle the pressure of Boston. They have an excellent player in Bay.
Tampa Bay- Carl Crawford- Crawford was one of the rare bright spots on the pre 2008 team. His speed made him an exciting player. However, don't mistake him for Juan Pierre as he can actually hit the ball. 2008 was not a good year for him though statistically. His stats declined across the board from the previous year. He posted an EQA in the .270's for the first time since 2004 when he was just 22. He made up by upping his fielding and it looks like an outlier to me. Established stars rarely hit their decline at 26.
Conclusion- Red Sox- Yankees- Rays- This one was especially tough. All three of these guys are good players but fall short of being superstars. In one draft of this post I had the exact reverse of what I have now. Bay is a fantastic hitter but his fielding has slipped a little. Now that he's with an actually competitive team, he may be motivated to improve his fielding which has slipped in recent years. Its hard to bet against a Boras guy heading into a contract year coming off the best year of his career at the plate though. So, Damon gets second. I went with Crawford at the back end on the off-chance that his 2008 wasn't just a fluke. In 2007 his BABIP was ridiculously high which helped to hide another down year in 2007. Honestly, this one was extremely close.