Jon Lester has repeatedly said that he is willing to give the Red Sox a hometown discount for an extension in order to stay and pitch for Boston in 2015 and beyond, just how much? We don’t know. The Red Sox as of right now have yet to start contract talks with Lester, which is somewhat concerning given he will be a free agent at the end of the 2014 season, along with his desire to remain with the Red Sox. There are a couple reasons as to why the Red Sox are hesitant to sign their opening-day starter for the past 3 seasons to a long-term deal.
There has been an emergence of talented young arms that are on the verge of being ready to contribute to the major league club. In AAA Pawtucket alone, there are three pitchers who saw time last year that could help out again in 2014. Allen Webster, who came over from the Dodgers in the 2012 salary dump, made seven starts last year, but struggled tossing a 8.60 ERA. This number is somewhat inflated, due to two starts against Seattle and Minnesota in which he only managed to go a total of 4.0 innings allowing 15 runs, but without a doubt he has talent that will become more refined as he matures. Brandon Workman impressed many in his stint with the Red Sox. He is a starter and projects to remain there, but he was primarily used out of the bullpen last year and has won over some fans thanks to his playoff performance: 8.2 innings 0 earned runs. Finally, knuckleballer Steven Wright saw limited time last year, but doesn’t figure to see the major league club too much this year thanks to added depth. In addition to the three pitchers mentioned above, top prospects Matt Barnes (AAA) , Anthony Ranaudo (AAA), and Henry Owens (AA) haven’t even been on the major league club and they are big plans in the Red Sox future.
The other major reason the Red Sox might pause before opening a conversation with Lester is his 2012 season. Lester looked lost much of 2012 and couldn’t seem to get himself on track. He returned to old self this past season posting a 3.75 ERA, but it was still higher than his ’08-’11 seasons in which his ERA was never higher than 3.47. A thought coupled with this is that Lester could be getting old, but he is only 30 years old and to use a measuring stick as to what he might deserve, the best comparison to Lester would be Cole Hamels. Hamels was two years younger than Lester when he signed a six year $144 million dollar contract. They are very similar, both star lefties for high payroll teams and their seasons leading up to the contract year are very similar, with Hamels having a slight edge number-wise. Hamels earned his way into $24 million a year, which doesn’t sound like too much of a discount for the Phillies.
Lester on the other hand wants to stay in Boston to the point that he is willing to leave some money on the table. This doesn’t mean Lester would come cheap, especially considering his World Series performance, which would have given him a World Series MVP award if David Ortiz hadn’t hit an other-worldly .760 against St. Louis. Still, in an age where star lefties are starting put themselves in the $30 million a year range (yes, you Kershaw), if Lester hit the open market, it would not be a surprise if he were to receive an offer for 5 years around $125 million. Given his willingness to provide the Red Sox with a discount, a fair deal for both sides would be something in the 4 year $80-88 million range. This would retain the Red Sox most consistent pitcher for the foreseeable future and not to mention, provide the young studs with a veteran leader. So, what do you think should the Red Sox sign Lester to an extension or do they allow him to hit free agency.