He, along with Josh Beckett, struggled mightily down the stretch last season, going belly up as one of the main culprits in the Red Sox' September collapse. It was then revealed that he was one of the pitchers involved in the chicken and beer saga.
This season hasn't been much better, really, as Lester has struggled to find any sort of consistency (along with Beckett as well). The big left-hander has been better of late, but there's no doubt it's been a tumultuous year.
When you add in all of the outside drama that has surfaced within the last couple of weeks, it's easy to understand why Lester might be feeling a little jaded. He was asked about whether or not he feels Boston is still a place where players want to play, and he didn't sugarcoat it.
"I don't know," Lester told the Boston Herald on Thursday. "It's always been a demanding place to play, but until the last two years, it always was about baseball. Now we've got things written and said about guys' personal stuff as human beings, as people. Now you're starting to question people's manhoods. That's where it gets hard."
Lester isn't the first person to question whether Boston is still somewhere that baseball's best players want to play.
Manager Bobby Valentine discussed that notion just a day earlier.
From what I gather, it's what's happened here," Valentine told WEEI on Wednesday. "All this noise is one of the reasons that players don't like to sign here because they don't have to deal with this in other markets. They don't have to deal with the 'drama of the day' type of situation. They can go out and play baseball.
"What I told [the players] is that this is what we signed up for. We can't control what goes on out there, but we can control what goes on in here."
This isn't the first time that Lester has wondered aloud about the benefits of playing in Boston. In fairness, Lester has said repeatedly that he enjoys playing in Boston, but years like these will certainly test someone.
"I think if you asked [Kevin Youkilis] that he'd say the same thing. Hey, I love it here, but I don't know if a change of scenery is good," Lester told ESPN.com back in July. "I haven't had a change of scenery. I think when you leave Boston, unless you go to a New York or Chicago, it can't do anything but help you.
"This is a tough place to play, you know? I love playing here because it makes people accountable. It makes you accountable for what you do. There's no excuses here. If you pitch like [expletive], you can't come in and say, 'Aw, the mound's a little wet' because you've got [groundskeeper Dave Mellor] down there saying, 'No, it wasn't.' This place makes you accountable. I love that about this place because I'm an accountable person. I always have been. My dad has ingrained that in me: Be accountable.
"I love that part about this place, but I think if you go from here to, I don't know, Texas, it would probably be easier to play. You don't have to worry about other things. You just go out and play."
Lester is 6-10 this season with a 5.20 ERA. He has shown some signs of improvement, though, with a 3.48 ERA this month and 23 strikeouts in 20 2/3 innings. He'll be back on the mound this weekend in New York on the heels of a 12-strikeout performance last Sunday in Cleveland.