- Gordon Edes, Red Sox reporter, ESPNBoston.com
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Presumably, those conversations are taking place at the ownership level, at which Boston's big-money decisions are always made. The source, however, said he wouldn't make any predictions regarding the outcome.
All along, Lester has added a caveat to his preference that the Red Sox not reopen talks until after the season. He said it last month in New York after he outdueled Yankees ace Masahiro Tanaka.
"If they make an offer that's right there [at market value]," Lester said then, "yeah, then maybe something can get done."
The realist in Lester says that the window at the All-Star break isn't long enough to bridge the gap between the club's offer in the spring (four years, $70 million) and what he believes he should be paid, even factoring in any kind of "hometown discount."
Boston's initial offer was far below market value in both dollars and years, although the presumed sticking point is expected, in the end, to be the length of the deal. One way the Red Sox could strike a middle ground is to offer Lester an attention-grabbing amount closer to, say, $30 million a year than to $17 million, for three years, perhaps with an option for a fourth year.
Asked if the Red Sox would make another offer to Lester over the break, Red Sox general manager Ben Cherington answered, "I can't say. We're going to honor the commitment we made not to talk about this publicly. We're also trying to honor and respect his desire not to talk about this publicly and become a distraction."
Cherington also said that the Red Sox's place in the standings (they're last in the AL East) didn't impact their desire to retain Lester.
"We've had interest in signing him going back to last offseason in March and still do. Everyone knows that," Cherington said. "I think that process is guided by things we see and think about a player. We certainly see him as part of making us good."
Assuming he stays healthy, Lester, 30, would then be in position to enter the free-agent market again, although with considerably less leverage at age 34. And given that Detroit's Max Scherzer this past spring rejected a six-year, $144 million offer from the Tigers to re-sign, Lester could well decide that offer still is far below what he could make on the open market.
Watching with keen interest is fellow Red Sox pitcher Jake Peavy, who admits he carries a bias into any discussion about Lester.
"This is somebody I'm very emotionally attached to," Peavy said Tuesday night. "Jon, we'll be friends for life. We love each other. Kinfolk we are. Me speaking on his behalf, that needs to be understood.
"I love the Boston Red Sox and respect everybody, but my heart and soul is with Jon Lester. This guy is as good as anybody in the game right now.''
Peavy understands he's welcoming a debate with those who promote Clayton Kershaw or Felix Hernandez or Tanaka, among others, as the game's best starting pitchers. But one thing they don't have, Peavy points out, is Lester's record when most is at stake.
In 11 postseason starts, Lester is 6-4 with a 2.11 ERA. In World Series games, his record is 3-0 with a 0.43 ERA. He beat the Cardinals twice last season in the World Series, won by the Sox in six games.
"What he did on that stage,'' Peavy said, "showed what he is. He almost single-handedly won us that World Series."
Peavy said Lester "loves Boston" but that he is in a "unique situation," one in which Boston's current last-place standing, combined with his continued superiority on the mound (2.73 ERA, which is almost a run better than the league average; 122 strikeouts in 122 innings; and career lows in home runs per nine innings and walks per nine) have only increased his leverage.
"I know they want Jon here," Peavy said of the Red Sox. "I know Jon's wishes are to stay here. That being said, with the way things went this spring, it's hard, the later it goes.
"I mean, a little more than three months away from free agency, it becomes really, really hard. I want the best for the Boston Red Sox. I want the best for Jon Lester. It's going to be interesting. I'll be interested."
The Red Sox are continuing "conversations" that could lead to another offer to free-agent-to-be Jon Lester, according to a major league source.