Entering the final year of his contract, Lester is fully aware of the monster deal Clayton Kershaw signed with the Dodgers earlier this month and the one Masahiro Tanaka has signed with the Yankees. But as much as Lester is awed by those types of numbers, they don't drive him.
Much like teammate Dustin Pedroia, who signed a seven-year extension last July, Lester simply wants a fair deal that will enable him to stay in Boston.
"I want to stay here," said Lester, who was in town for Thursday night's Boston Baseball Writers Dinner. "This is what I've known. I've grown up in this organization. I've had plenty of good times and plenty of bad times here. I enjoy it. My family loves it here. All my son talks about is going home to Boston. I mean, that's what he thinks is home.
"If it all comes down to it, we want to be here. It's hard to talk a deal now. I just can't really fathom signing a piece of paper like a Tanaka deal. Kershaw ... is completely out of the realm. But you look at these deals, it's out of this world. It's stuff you can't even imagine until it's put in front of you. Until that day comes, it's hard to talk about it. But the stuff you can talk about, like wanting to stay here and compete -- that's what we want to do."
Atlanta is where Lester resides during the offseason. Tacoma, Wash., is where he grew up. But from April through October, he is proud to represent Boston, and there's no eagerness to see what another baseball city would be like.
Lester has already won two World Series championships with the Red Sox, and he hopes to be around for some more.
"I understand that to stay here you're not going to get a free-agent deal. You're not going to do it. You can't. It's not possible," said Lester. "You're bidding against one team. I understand that 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. I want to stay here."
Lester is the first to admit that much like his friend Pedroia, he's a creature of habit.
"I've grown up with Pedey in the Minor Leagues and watched him turn into what I consider the best second baseman in the league," Lester said. "I don't want to leave that and leave this organization to go just for a few dollars to go try something new. I don't like new stuff."
The Red Sox, if they had their druthers, would keep the ace they have rather than look for a new one after the 2014 season.
"I think ... there are guys that move into a category that I think makes them a little different and gives them the right to have a conversation, and Jon's in that category, and Dustin's in that category, and David Ortiz has been in that category, and there will be others," said general manager Ben Cherington. "When guys are in that category, we want to keep a dialogue going. The door is open and we'll do that with Jon, and I'm sure there will be a conversation. But until we get to that, it's hard to say much more than I'm glad he wants to be here and we want him to be here, so we'll see where that leads to.
"A guy like Jon Lester, we'd love to keep in the organization, but because we haven't really had a conversation yet, I don't want to start putting a calendar on it; I don't want to limit ourselves or limit the process in any way. We haven't even gotten into the process yet. We certainly share an interest in talking about a way to keep him here, and we'll find a time to do that, to start that conversation."
Perhaps a deal could get done in Spring Training, but these things can sometimes take a little longer.
"I don't know. We worked really hard with Dustin last spring, and we weren't able to get one done by the end of Spring Training," said Cherington. "But we've got a good relationship with [agent] Seth [Levinson] ... and that entire firm. They may not want to spend as much time in Fort Myers or listening to me as they have in the past year, but the relationships are solid, so we'll be able to sit down and have a productive conversation."
These are good times for Lester, who is coming off one of the best postseasons by any pitcher in Red Sox history and looking forward to attempting a repeat.
"I feel good. I threw my first bullpen [session] yesterday," said Lester. "That was atrocious compared to what I remember things being. But physically, I feel good. Workouts have been going well. I'm ready just to get some sun and some warmer weather."