Jon Lester laughed out loud when asked Thursday if he had taken notice of the lucrative contracts landed by fellow starting pitchers Clayton Kershaw and Masahiro Tanaka this offseason.
“It’s hard not to pay attention to it,” the Red Sox lefthander said.
The Dodgers retained Kershaw this month with a seven-year extension worth $215 million. On Wednesday, the Yankees invested $155 million to sign Tanaka for seven seasons.
Lester, who is signed through the end of the 2014 season, is one of the pitchers next in line for a new contract. He hopes to start negotiations with the Red Sox in spring training and acknowledged he would take a discount to continue his career in Boston.
“These guys are my No. 1 priority,” he said before the 75th annual awards dinner, hosted by the Boston Chapter of the Baseball Writers’ Association of America at the Westin Copley Place.
Lester spoke candidly about his desire to stay with the Red Sox, acknowledging a loss of leverage if he signs in the next few months instead of determining his value via free agency after the season.
“I understand to stay here, you’re not going to get a free agent deal. You’re not going to do it. It’s not possible. You’re bidding against one team. I understand you’re going to take a discount to stay,” Lester said.
“Do I want to do that? Absolutely. But just like [the Red Sox] want it to be fair for them, I want it to be fair for me and my family. If we can get to something in spring training, that would be awesome.”
Sam and Seth Levinson, the agents who negotiated the eight-year, $110 million extension for Red Sox second baseman Dustin Pedroia last season, also represent Lester.
Lester sees that deal as a template of sorts.
“We all understand. Pedey, he left a lot of money on the table to stay here. That’s what he wanted to do,” Lester said. “I understand that. That’s my choice; that’s his choice; that’s all of our choices. But at the same time, you don’t want to be the guy that makes that market come down a little bit.
“I want to win. If that means taking a Pedroia deal where you stay here for less money to be happy and be competitive and win every year, let’s do it. Let’s get it done.”
General manager Ben Cherington said negotiations have yet to start. But he acknowledged a desire to keep Lester.
“Because we haven’t even had a conversation yet, I don’t want to start putting a calendar on it,” he said. “But we certainly share an interest in talking about a way to keep him here. And we’ll find a time to do that, start up that conversation.”
Red Sox owner John Henry has said he wants to limit long-term deals to players like Pedroia, who were developed by the organization and are trustworthy.
Lester, manager John Farrell said, fits that definition.
“I hope he remains here long term and I know we’ll have those discussions,” Farrell said. “Ultimately, we’re betting on people. When we’re all away from the ballpark and you go to sleep at night, are you confident an individual does the right things? With Jon Lester, you have that.”
Said Cherington: “I think Jon’s certainly in that category. Dustin was in that category. David Ortiz has been in that category. There are others who will be in that category. So when guys are in that category, we want to keep a dialogue going. We want to keep a door open and we’ll do that with Jon.”
Lester’s timing is perfect. He was 15-8 with a 3.75 earned run average last season before going 4-1 with a 1.56 ERA in five postseason starts. Lester was brilliant in the World Series, allowing one earned run on nine hits over 15⅓ innings and striking out 15.
Lester also gained a greater level of personal comfort, forging strong relationships within the clubhouse and softening what often was an angry persona in previous years.
“I enjoy it. My family loves it here,” Lester said. “When it all comes down to it, we want to be here.”
If no deal were in place by Opening Day, Lester would prefer the sides table discussions until after the season.
“That way, everybody’s relaxed and everybody is in the same place and then when the season starts you don’t have to worry about it and just focus on baseball,” Lester said.
“Hopefully we can do that one way or the other. I would like to, if we don’t get something done, to try to put it off as long as we can to not make it a distraction.”
Again, Pedroia’s contract could serve as a road map.
“We worked really hard on Dustin last spring and weren’t able to get one done by the end of spring training. But we got a good relationship with Seth and the Levinsons and that entire firm,” Cherington said. “The relationships are solid. So we’ll be able to sit down and have a productive conversation, I’m sure.”
Lester threw off a mound for the first time on Wednesday, about 10 days later than usual. Because he made those five extra starts in October, the Red Sox will bring Lester along carefully in spring training, scheduling him for five starts prior to Opening Day.
“I’ve felt good throughout my workouts. I haven’t felt anything that stayed with me through the season. So far, so good and I’ll continue to build off yesterday and be ready for spring,” Lester said.