The Boston Red Sox have made one of their biggest mistakes probably since letting Ruth go to the Yankees in 1920. I think all Sox fans are shocked that the Red Sox have not resigned Jon Lester to keep him in Boston for the foreseeable future. Early in Spring Training a report came out that Jon Lester wanted to stay in Boston and was willing to take somewhat of a hometown discount without hurting the market for future free agents. Many thought that a deal would absolutely be done but for whatever reason Red Sox ownership only offered Lester 4 yr / 70 Million and he said no without hesitation. Lester just came off an unbelievable Postseason where he went 4-1 with a 1.56 Earned Run Average in 34.2 innings while only allowing 25 hits. Lester also performed when the lights were at their brightest in the World Series going 2-0 in 2 starts with a .59 ERA. Why the Red Sox thought they could get Lester to sign by offering him well below his actual value is baffling. The Red Sox decision to be frugal with their money, an organization that ranks 4th in payroll (162, 817,411), will either cost them millions of dollars or cost them their ace.
Lester was drafted in the 2nd round in the 2002 draft by the Red Sox and made his major league debut 4 years later. Since making his debut, he ranks 9th all-time in Sox history in wins (110) and 4th all-time in strikeouts (1379). The definition of an ace in the big leagues is every time that pitcher makes a start, his team knows he will go deep into the game and give his team a chance to win and Lester has done just that. He ranks 9th among active pitchers with a winning percentage of .6337 and has made at least 31 starts in each of his first 6 full seasons in the big leagues. Aces do not grow off trees and it would be difficult to imagine what the Sox rotation would look like if Lester were not a part of it next season.
Not counting Lester, next year’s rotation has Lackey, who only makes league minimum due to his Tommy John Surgery in 2012, Buchholz, who has been injured over each of the past 2 seasons, Ruby De La Rosa, who threw 110 innings in 2010 for his career high, and Brandon Workman, who has never thrown over 140 innings. Pitchers who can consistently throw 200 + innings every year are invaluable and John Lackey is the only Sox pitcher besides Lester who has thrown 200 + innings (once with Red Sox). If the Red Sox were to lose Lester, it would be a tremendous hit to the Sox rotation not just in 2015 but for future years. The Red Sox cannot rely on any of their starters to be a lock for 200 + innings because none of them have proven they can except for Lackey but even he hasn’t done it since his TJ surgery. The Red Sox have no choice but to sign Lester for whatever the amount will end up being and they have absolutely no leverage when it comes to discussing his contract
Right now 63 starting pitchers make more money than Lester’s 6 million dollars. Lester has been a steal for the last couple of seasons but he has performed at a level with the top starters in the game and it is time his contract agrees with that statement. Two pitchers that have deals that could be similar to Lester’s are Homer Bailey and Cole Hamels. Bailey signed a 6 yr / 105 Million dollar deal and is only 7 games above .500 for his career. Hamels signed a 7 yr / 153 Million dollar deal and has similar numbers to Lester’s. I would expect Lester’s deal to be between Bailey’s and Hamel’s deals but the more he throws this season, the more the Sox will end up paying. Through 20 starts in 2014, Lester is 10-7 with a 2.50 ERA. Sox fans need Lester to continue his domination in order to get back into playoff contention but the more he continues to dominate, the tougher it will be to resign him.
Lester will be 31 years old entering the 2015 season so he still is relatively young and he understands how to pitch. Not only does he have a good fastball, he locates his pitches well and can cut and sink the ball. Lester has also show a plus curveball this season as his pitching style should be successful as his stuff slowly begins to decline as he gets older. Lester is a fan favorite in Boston and it would be a devastating loss for the organization if he decides to go to a new club. If the Sox are unable to resign him, it will send an interesting message to the rest of the club and a message that could upset the veterans on the team. I know I am not alone in saying that this deal must get done no matter what the cost is because Lester is too valuable to the future of the Boston organization. My advice: Sign Lester now because each start will end up costing the Sox in the offseason.