Locking up Dustin Pedroia through 2021 on a team-friendly $110 million contract represented a monumental step by the Boston Red Sox to remain a formidable contender for the long term. Inking Jon Lester to a lengthy deal and retaining the anchor to what has become a strong starting rotation would further bolster general manager Ben Cherington’s goal to battle for a playoff spot every season.
The 30-year-old Lester, who is 100-56 with a 3.76 ERA over eight Major League seasons and is 3-0 with a 0.43 ERA in three World Series starts, has proven himself as one of the top pitchers in baseball since 2008, aside from a disastrous 2012 campaign. He is eligible to become a free agent after this season, but chances are the Red Sox will sign him to a new contract, and the Washington native has said multiple times that he wants to remain in Boston.
“I don’t like change,” Lester recently said. “I like being where I’ve been. I like the people. I like the surroundings. It feels like home.”
Interestingly, Lester and Pedroia share the same agents, brothers Seth and Sam Levinson. Last summer, Pedroia agreed to an eight year, $110 million contract leaving millions of dollars on the table to stay with the only organization he has known since the Red Sox made him a second round selection out of Arizona State University in 2004. Lester was a second round pick in 2002 out of high school. Both players have two World Series rings and, if Lester signs a new deal, both players will be in prime position to experience more championships in Boston.
Armed with one of the game’s best rotations (Lester, Clay Buchholz, John Lackey, Felix Doubront and Jake Peavy), a deep and talented bullpen, a productive lineup and a well-stocked farm system, the Red Sox will try to become the first team in baseball to repeat as World Series champions since the New York Yankees did so in 2000.
Regardless of whether they accomplish that feat or fall short, Boston expects to contend for the long term because of the aforementioned factors, and coveted payroll flexibility. After this season, the only Red Sox players who are signed beyond 2015 are Pedroia and Buchholz. Thanks to impressive young names like shortstop Xander Bogaerts; center fielder Jackie Bradley; Jr.; third baseman Garin Cecchini; catchers Christian Vazquez and Blake Swihart; starting pitchers such as Allen Webster, Anthony Ranaudo, Matt Barnes and Henry Owens; and relievers like Rubby De La Rosa, Drake Britton, Brandon Workman and Noe Ramirez; the club has talented depth that will allow them to replace many veterans from within, freeing up significant money to trade acquisitions and free agent signings.
Lester will make his Grapefruit League debut on Monday against the Tampa Bay Rays at JetBlue Park in Ft. Myers. The Levinson brothers were in Ft. Myers last week, and there is speculation that a new contract for Lester could be signed before Opening Day.
The price of pitching is costly. Clayton Kershaw ($215 million, seven years), Masahiro Tanaka ($155 million, plus $20 million posting fee), Homer Bailey ($105 million, six years) and Adam Wainwright ($97.5 million, five years) are examples. Lester is in a class among the game’s elite starters, and he said he is willing to accept what he termed a “hometown discount.”
With their payroll flexibility, the Red Sox should have no problem accommodating Lester and, if he remains healthy and productive, David Ortiz. Of course, chances are Lester’s new deal will happen much sooner than an extension for Ortiz.
Even with the array of high ceiling starting pitching prospects – and the emerging Doubront – the Red Sox need Lester to sit atop the rotation beyond 2014. His is a deal that should and will get done.
