Jon Lester’s Contract Negotiations With Red Sox Will Test Each Side’s Loyalty

Jon LesterJon Lester and the Boston Red Sox will soon sit down at the bargaining table. Each side’s loyalty will be tested.

Lester was crystal clear Thursday. The two-time All-Star said that he not only loves playing for the Red Sox, but that he also would accept a hometown discount to remain in Boston beyond 2014. The question is whether Lester’s claims ultimately will be reflected in his negotiations with the Red Sox.

If Lester doesn’t sign an extension before hitting free agency next offseason, the left-hander will have several suitors, likely meaning a more lucrative contract. It’s a situation that Lester was well-aware of while speaking with reporters Thursday.

“I understand that to stay here [in Boston], you’re not going to get a free-agent deal. You’re not going to do it. You can’t. It’s not possible. You’re bidding against one team,” Lester said. “I understand you’re going to take a discount to stay. Do I want to do that? Absolutely. But just like they want it to be fair for them, I want it to be fair for me and my family. If we can get to something hopefully in spring training, that’s awesome. Like I said, I want to stay here.”

Lester’s agents, Sam and Seth Levinson, probably pulled their hair out Thursday listening to the pitcher profess his love for Boston. While refreshing in an age when so many athletes chase the almighty dollar, Lester’s comments seemingly swayed leverage in the Red Sox’ favor. If true, Lester’s desire to stick with the club that drafted him in 2002 could mean a team-friendly deal, especially if Ben Cherington and Co. drive a hard bargain and show an actual willingness to let the pitcher walk.

Clearly, the two sides would like to extend their rewarding relationship, though. And why not? The Red Sox have won two World Series titles with Lester serving as a legitimate front-end starter, and Lester and his family love living in Boston. The question thus centers on each side’s definition of “fair,” because it’s already pretty obvious that both parties will need to make sacrifices.

Lester will need to suppress the temptation to chase — and likely land — the richest deal possible, while the Red Sox will need to back off their recent reluctance to hand out long-term contracts. If one side doesn’t hold up to its end of the bargain, things could get messy. Such is the case when a longstanding, tight-knit relationship enters a critical stage — in this case, free agency — because there’s the potential for each side to feel like it’s owed something.

Dustin Pedroia and the Red Sox were able to hash out a very reasonable $100 million contract extension last season, and it’s because both the player and the organization entered into discussions with reasonable expectations and the understanding that sacrifices would be made. The Lester situation appears to be heading down a similar path, assuming that Thursday’s media availability wasn’t just a dog and pony show.

Lester and the Red Sox might experience some discomfort at the bargaining table as financial hopes cross paths with personal desires. But an agreement remains the best-case scenario for both sides, and it should come to fruition with some open-mindedness.

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