1. Jon Lester, Boston Red Sox
Jon Lester has just as polished a resume as David Price except with two World Series rings added to the mix. Like the other players on this list, Lester has been a lifer with his first team, coming up with the Red Sox in 2006 and never looking back. He is 109-63 with a 3.66 ERA in his career. So why have the Red Sox not given Lester a long-term deal in the final year of his contract? Since the Carl Crawford-Adrian Gonzalez debacle, the Red Sox have shied away from big deals that usually come back to haunt teams.
Lester is likely looking for Tanaka (if not Kershaw) money in 2015 and beyond, but the Red Sox probably won’t give him that. What would they get by trading Lester as a rental to a contending team in 2014? They would likely get a nice prospect or two. Better yet, the goodbye needn’t be forever. After the Red Sox finish their not-so-promising 2014 season, the two parties coud get together and make a deal for the future. The price would be just a few months of separation, but the return would be considerable for the Red Sox as an organization.