Jon Lester
After winning 97 games in the 2013 Major League Baseball regular season, the Boston Red Sox would go on to win their eighth World Series Championship in franchise history. This season hasn’t been as smooth for the Red Sox as they are currently have a record of 36-44. The Red Sox are currently in fourth place in the American League East as they’re eight games behind the first place Toronto Blue Jays. Barring a turnaround over the summer the Red Sox are staring down the barrel of their second losing campaign in the past three seasons and they would also be the second consecutive defending World Series Champion to have a losing season. Surprisingly one man that could benefit from the problems in Boston this season is starting pitcher Jon Lester.
Lester is in his ninth MLB season (all with the Red Sox) and he is set to be an unrestricted free agent this winter. In spring training the Red Sox and Lester attempted to negotiate a contract extension, but with both sides far apart on the finances they walked away from the table. Lester and his agent John Yates are not expected to negotiate with the Red Sox for the remainder of the regular season which will allow Lester’s value to potentially increase heading into the winter. By the time that the 2015 Major League Baseball season rolls around Lester will be 31-years of age and like the other 29 MLB teams, the Red Sox should be wary of offering Lester a long-term deal. But will they do it?
This season Lester is leading the Red Sox pitching staff in wins (8), earned run average (3.14), and strikeouts (109). Lester’s 3.14 earned run average is the lowest of his career and he is also on pace to throw 200 innings for the sixth time in the past seven seasons. Regardless of how this season will pan out for the Red Sox they could face some competition in order to retain Lester in the off-season.
Lester is making $13 million this season and he and Yates know that the pending free-agent market for left-handed starting pitchers is a slim one. Lester won’t be the highest sought after pitcher this off-season as that distinction will fall upon Detroit Tigers starting pitcher Max Scherzer. But more than likely Lester is going to want a six-year deal in the range of $120 million and he’ll get it and more if pitching is at a premium.
Ben Cherington
Unlike his predecessor Theo Epstein, current Red Sox general manager Ben Cherington plays it closer to the chest in negotiating with pending free agents. But the strategy has already hurt him.
After seven seasons with the Red Sox, outfielder Jacoby Ellsbury hit free agency last winter. Ellsbury is represented by super agent Scott Boras who is infamous for having “mystery teams” that want the services of his clients. Cherington chose not to get into a bidding war for Ellsbury who would go on to sign a seven-year, $153 million with the New York Yankees.
This season the Red Sox have the second oldest team in MLB and if Cherington’s track record is any indication, he could be willing to allow Lester to leave Boston.
In recent years we have seen teams suffer after giving players over the age of 30 long-term deals. The Los Angeles Angels have found this out the hard way over the past few seasons with the lucrative deals that they handed out to first baseman Albert Pujols and outfielder Josh Hamilton respectively. In Epstein’s last season with the Red Sox, he signed outfielder Carl Crawford to a seven-year, $142 million deal. Crawford was coming off of a career year with the Tampa Bay Rays and he would turn 30 midway through his first season with the Red Sox as he never lived up to the hype before he was traded to the Los Angeles Dodgers in 2012.
Since 2000, the Red Sox have been one of the best MLB franchises as far as drafting and developing their players which is why they have won more World Series Titles (3) than any other Major League Baseball team over that span. The Red Sox will need to be revamped in the outfield and at shortstop in the off-season. And with those glaring needs I doubt that Cherington will go all out in the effort to retain the services of Lester which means that following the 2014 World Series, the bidding war will begin for his services.
Source: Baseball-reference.com
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