To the average fan, the offer to Jon Lester offer of $70 million over four years ($17.5 million per year) is not much of a hometown discount. Such a contract would make Lester only the 12th (tied) highest paid starting pitcher in the major leagues (and the third highest at the field in the Bronx). If it were as high as $80 million ($20 million per year), the list shrinks a bit (11th alone) People generally don’t understand that these players are in competition with each other salary-wise, so what seems like an obscene amount of money is, in reality, what the market will bear, and a matter of status, which, to some, can be as important as the dollar amount.
Another factor to consider is that at even $80 million, it would not be the largest contract for a starting pitcher in team history. Lester’s own teammate John Lackey signed an $82.5 million contract over five years. Certainly such a fact is not lost on Lester. His agents would likely remind him that there are only three of the twelve higher paid starting pitchers (Wainwright, Cain, and Lincecum) with two rings in their pocket such as Lester possesses. While the health of a starting pitcher is more precarious than a position player such as Dustin Pedroia, the team was willing to go to eight years with Pedroia. Lester is not going to want to have to go back into free agency at the age of 34. He would want at least the five years given to Lackey (who had health concerns as evidenced by his Tommy John surgery) and in excess of $100 million. Another point to consider is that the team (in the Francona era) was willing to give Adrian Gonzalez $154 million and Carl Crawford $142 million and neither had the eight years and two rings that Jon Lester has.
This writer tends to fall on the side of putting up a contract that would pay Jon Lester more than $20 million per year for at least five to six years. His durability, his grit, his 101 wins (.633 winning percentage), and 2.11 postseason ERA (0.43 in the World Series) in a Red Sox uniform should bring forth this kind of offer. The argument has been made that the team has an abundance of young pitching on the way and the team does not want to saddle itself with the contract of more than $20 million for at least 5 years. My argument to that is that is the going rate for pitchers of Jon Lester’s caliber. There is a reason there are only three starters with two rings (only one of which who won both as a starter) above that contract offer. It is because those guys are special and you can’t let them get away.
Don’t lowball Jon Lester. He is an elite pitcher. Pay him like one.