Jon LesterJon Lester understands the reality that this could potentially be his last season with the Red Sox. The lefty hopes that it isn’t, though, as Boston is where he wants to be.

Lester is slated to become a free agent following the 2014 season, and Jacoby Ellsbury‘s recent departure reminded everyone that the business side of baseball often prevents teams from keeping their homegrown talent. Each case is different, however, and Lester said Thursday on WEEI’s Hot Stove Show that he hopes his future involves staying with the organization that drafted him in 2002.

“Obviously, it’s crossed my mind. But it’s not something that’s really set in for me yet. I feel like I’ve got one more year here and we’ll go from there,” Lester said. “I’m sure there will be some form of communication [with the Red Sox about a new contract], I would imagine probably in spring training, hopefully in spring training and hopefully during the season sometime if not in spring training. Obviously, Boston’s my home. This is all I’ve known. This is all I’ve become accustomed to, and all I want to know. My family enjoys it up there. I enjoy playing up there. There’s a lot of factors in it. At the same time, kind of like Jacoby, there’s a business side of everything and you’ve got to look at it that way. Same thing with the Red Sox. … Sometimes you have to part ways. Hopefully, that’s not the case when it comes down to us here in the future.”

Lester is coming off a solid bounce-back campaign in which he went 15-8 with a 3.75 ERA in a career-high 213 1/3 innings during the regular season. The hurler’s true value shined through in the postseason, though, as Lester went 4-1 with a 1.56 ERA in five playoff starts. The postseason success — which has become a hallmark of Lester’s game — included two World Series wins in which the southpaw outdueled Cardinals ace Adam Wainwright.

It’s unclear what kind of deal Lester is looking for, but there’s a chance that he could be the best pitcher available on the open market next winter if the Tigers end up signing reigning Cy Young winner Max Scherzer to a contract extension. It’s obviously an enticing possibility for Lester, although the 29-year-old insists that there’s numerous variables that go into contractual decisions.

“You sit down with your agent, sit down with your family and realize, yeah, there’s possibly millions of dollars that you left on the table. But at the same time, you’re secure. Your family is secure,” Lester said of his first contract — a five-year, $30 million deal that he signed prior to the 2009 season. “You’re with the team and you don’t have to worry about anything. And the same thing will go here in the next couple months or the next however many months. If you sign a deal before you become a free agent, you’re probably most likely leaving money on the table.”

While Ellsbury netted a seven-year, $153 million contract in free agency this offseason, teammate Dustin Pedroia took a different route. The All-Star second baseman signed an eight-year, $110 million extension during the season that will run from 2014 to 2021, which is likely far less than he would have garnered if he waited and tested the open market.

“He left a ton of money on the table, but this is where he wants to be the rest of his career,” Lester said of Pedroia. “He sacrificed that to be here, to be a Red Sox. I think when you get down to that point, you have to weigh those options. You have to sit down and decide. We’ll obviously hopefully have those talks here the next couple months.”

We’ll see if Lester is willing to make a similar sacrifice.

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