Jon Lester won't be a free agent until after 2014, as the Red Sox will pick up his $13 million option for next year. When he is a free agent, though, a significant payday can be expected, barring short-term catastrophe. FOX Sports' Ken Rosenthal said as much on the Dennis and Callahan Show on Wednesday morning, saying that Lester could "expect" between $146 million and $210 million on his next contract.
There's a whole lot to unpack from that statement. First off, you can forget about $210 million or anything approaching it: Lester is not going to pull in money that's been handed out to (or will be handed to) only Felix Hernandez, Justin Verlander, and Clayton Kershaw. Unless Lester pulls a 2010, Cy Young-caliber season out of nowhere, or pitches like he has this postseason for an entire year, that's just not in the cards, and it's a little weird to even suggest, at this point, that it's a possibility.
The $146 million, however? That sounds more reasonable, at least in terms of someone being likely to give it to Lester should he approach free agency. Zack Greinke, heading into his age-29 season, signed for six years and $147 million with the Dodgers before the 2013 campaign. Lester is the same age as Greinke, so he would be heading into his age-31 campaign when he hits free agency, making a match less likely, but someone with the proper balance of desperation and cash flow could make Lester that rich.
This is where Boston's advantage of already having Lester under control could come into play. They can negotiate with Lester starting right now, should they choose to, and by giving him offers a year before he is able to hit the open market, they might be able to reduce the average annual value of any deal simply by guaranteeing him a pay day now instead of 33 starts or 200 innings from now. They also have the benefit of legacy and pride on their side, and if you're already going to be rich, that sort of thing can matter to the right player with the right organization -- for instance, how much more money would Dustin Pedroia or Evan Longoria made had they waited? If Lester re-signs with the Red Sox, the organization he's been with since he was drafted back in 2002, it's basically a given he'll retire as their greatest lefty ever, and if he keeps it up in the postseason, he'll take top honors there as well. He was charged by the front office and coaching staff with becoming the leader of the rotation in the clubhouse, and all indications are that he's met that challenge, likely making him ready to be the pitching version of Pedroia the Red Sox need for when the pitching prospects make their way to Boston.
Will all of that matter to Lester more than an extra $20-30 million on his deal? That's just something we're going to have to wait and see. But, given the market for the likes of Anibal Sanchez just one year ago, it doesn't seem crazy to believe, despite what Rosenthal has reported, that Lester could be had by Boston for something more reasonable that comes cheaper than that $146 million floor. Given Pedroia is making just $110 million over eight years on his new extension, and the Sox seem to be recoiling at the thought of a deal for free-agent-to-be Jacoby Ellsbury that surpasses that, we can likely infer that Rosenthal's numbers are a non-starter for the Sox. We'll likely know soon enough, though, since, regardless of outcome, the offseason starts on Friday at the latest for the Red Sox.
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