5. Dontrelle Willis
The Sox turned to the Florida market last winter, landing Josh Beckett and Mike Lowell at a dear price -- Hanley Ramirez may have been the NLs best rookie and Anibal Sanchez threw a no-hitter. But if the Marlins decide they have enough young pitching and elect to part ways with Willis, who could command an $8m salary in arbitration next season, the Sox should consider revisiting John W. Henrys ex-team again. Willis is young, charismatic, and intensively competitive, a great fit here.