Discussion: It’s Time to Let Go of Jon Lester

Last night, BP Boston’s Brett Cowett and I bonded over this correct and binding tweet, by me:

I hereby declare a moratorium on whining about Jon Lester no longer being on the Red Sox. Thank you for your compliance. — Admin

— snakes (@bryanjoiner) October 24, 2016

Even if (definitely not) the editor of this site did not agree:

@bryanjoiner

Bryan,

Jon Lester should be a Red Sox

— Def Not Ben Carsley (@BenCarsley) October 24, 2016

Which got Brett and I thinking: Why can’t we quit Jon Lester? We headed to email to figure it out. The conversation is below and has been only lightly edited for clarity, because we’re generally clear AF:

Bryan: This will be fun. I’ll basically let you start, here’s the softball. You and I are both sort of sick of the bellyaching over Lester, even if we love the guy. Why does it bother *you* so much? I have my reasons, but I’m curious about yours.

Brett: We get it — the Red Sox spent money elsewhere that wasn’t spent on Jon Lester. Yes, the Red Sox low-balled him early in 2014. Apparently, the thinking regarding that “insulting” offer is that it soured him on the idea of re-signing with them that winter, but it’s easy to forget that the Red Sox were one of the final teams he considered. It’s not like the $70 million offer they made in Spring Training made him think, “Well, screw these guys, deep dish pizza for life!” He wanted something different, and no amount of money that the Red Sox were willing to offer was going to change the mind of a guy who wanted a change.

The worst part is that this train of thought leads people to believe that the Red Sox signed Pablo Sandoval with all the money they *could’ve* spent on Lester, as if they had the divine power to choose between the two players with no outside influences. That complaint is so fraught with terrible reasoning that it hurts me just to mention it.

Bryan: I agree with this, and I’ll  throw this in there: They traded him! It was obvious why they did it, but once the seal was broken, I can see why he didn’t feel obligated to return to Boston — which was a total shitshow at the time, devoid of both the manager and general manager under whom he had played most of his career. So maybe he wanted a change, or maybe a change was forced upon him, and he just decided to roll with it … while making more money in the first place.

On top of that, it’s easy to lose sight of the fact that the Sox basically turned Lester’s contract year into Rick Porcello, who is the Cy Young Award favorite in the American League. I know that technically the Sox could have had their cake and eaten it too, but this seems to fall into the ever-expanding category of Sox fans taking the team’s success for granted and being overly melodramatic about the bad moments, or, in this case, merely less than perfect.

I also think that David Price’s relatively poor performance is overly influencing our thinking here, and I think Lester’s history with the Sox — beating cancer, anchoring a World Series-winning team — is properly influencing it, but my main complaint for the time being is that this World Series is not about us any more than the 2004 World Series was about the Cleveland Indians after their best player had decided to come here. All that said, I’m fine with people being pissy about it once the Series is over. I’m dead inside, but that doesn’t mean everyone else has to be. What about you? Do you think this is a temporary or permanent problem? And how do we solve it?

Brett: I agree with the fact that is isn’t about us anymore, because it really isn’t at all. I’m very okay with being happy for Lester and the other former Sox, because they were good and fun guys. They’ve moved on now, and so should we. Cheer for whomever you want. Sure, the Sox made bad choices revolving around these guys, but I’d rather focus on how they’re doing now, not how’d they be doing in Boston.

Personally, I think this is a temporary problem, but it all comes down to Price. People will lament not having Lester until Price finally turns in a postseason that equals the ace pitcher reputation he has. Until that happens, and as long as Lester is good, the complaining will continue. There’s nothing we can really do to solve it individually, barring a J.D. Drew-like change of heart. If Price never does that, and can’t live up to the very high expectations people set for him, then it’ll just become a constant source of regret, and we’ll never hear the end of it.

It just comes down to the players the fans have the most disdain for: Price and Pablo. Hanley and Porcello have redeemed themselves but if either has a bad 2017, you’re going to hear the same thing about both of them. They need to perform, because we’re not going to stop people from those dreaded hypothetical scenarios.

Bryan: The fun part is that if you dig into advanced stats, Price might have a better season than Lester. Baseball Prospectus (w00t) had Price at a 2.90 Deserved Run Average and 6.5 WAR and Lester at 3.10 DRA and 5.3 WAR. FanGraphs had Price at 4.5 WAR and Lester at 4.3. Only Baseball-Reference supports the results of the eye test; they have Price at 3 WAR and Lester at 5.3. You can take all these with enough salt to melt a driveway, of course, but it doesn’t change the fact that pitching in the NL Central is a far more desirable job than pitching in the AL East. Remember when Adam Vinatieri left the Patriots to go kick in a dome? Yeah, me too. This seems kinda like that.

I agree with you that we’ll probably never be rid of the hypotheticals until Price turns in a great regular season or postseason, but it’s important to remember that at this point last year Porcello was considered an utter failure, and we have short memories when it serves us to have them. I still have hope for Price, and I think the actual difference between him and Lester at this point is mostly academic. As much as Price is skewing our perceptions, so are the Cubs writ large versus the Sox — Boston’s organization is one of the best in the league, but there’s no question that Chicago is better right now, and Lester seems to benefit from his exalted company. To paraphrase “our” Senator (this is a very loose “our,” as neither of us live in Massachusetts), the Cubs have been great, but he didn’t build that organization: Theo did.

And there’s the rub. Epstein’s involvement, along with Lester’s and matched by Francona’s and Napoli’s on the other side, makes us feel heavily invested in the result of the series. “Invested” might be the wrong word, actually; I think we feel like we’re entitled to make judgments about these guys because they’re all Red Sox legends. I think we’re sort of right, actually, but there’s enough excess baggage with Lester than I think we generally go too far. I think you correctly ID’d not merely Price, but Sandoval, as the general catalysts for this, though I think there’s a compelling argument that if the Sox had made it out of the first round this would have been tamped down, and if they had made the World Series, it might have been smothered altogether.

Of course, none of that matters, and now I’m trafficking in hypotheticals. I guess my next and maybe last question is this: Do you think this is something we’ll still be talking about in 10 years? Like, when Price and Lester are both good and done, do you think it’ll still haunt and/or bother us? My suspicion is that it rests not merely on how the Sox do, but the Cubs as well. Given how well they’re set up, it seems like we might be talking about this for awhile.

Brett: A decade can change a lot of things. I don’t think Sox fans sorrowfully regret letting Pedro go after 2004 anymore, mostly because the teams in the late 2000s were so good. But I don’t think this’ll be something we’ll remember in a decade, especially if the Red Sox continue to make runs deep into October. Winning breeds forgiveness, at least partially. But you are right — the more successful the Cubs get, the more we’ll hear about it. It’ll only get magnified with how many more times the Cubs and the Red Sox make the playoffs and make a Boston-Chicago World Series a possibility.

I don’t think it’ll haunt the team that much, however. The Red Sox probably didn’t see Jon Lester as part of their new core, which will be based around the Killer Bs and how much they can grow. It hurt the Sox in the short-term because of how terrible the team has been with developing starting pitching. But looking forward, there are some things that can alleviate the Red Sox’s pitching woes. You have Michael Kopech and Jason Groome. You have the incredibly stacked 2018 free agent class. None of them will be Lester, and probably will never have the reputation he had, but it’s well worth a shot. Lester is not the only good starting pitcher out there.

It might end up being a footnote in 10 years, since something like that pales in comparison to the dumpster fire that was most of the 2012 season. In the end, if the Red Sox are good, and make the postseason a ton of times, does it really matter? The Red Sox are still successful! Just because one of the starting pitchers isn’t Jon Lester should be irrelevant. The Red Sox are playing in October. That much should be enough. Despite that, pundits will take their fortunes in the postseason as a microcosm of the previous six months, and keep bringing this up. Sooner or later, we have to realize that the Red Sox are succeeding without Lester, and we have to appreciate that. Would it be nice to have him? Sure, I’ll admit that. But the Red Sox do not. Oh well.

It’s better to put faith in the guys currently on the roster than pine for someone who isn’t there anymore.

Bryan: Aye, aye. Well said. We can leave it at that. I still pine for Jonny Gomes, though.

Photo by USA Today Sports Images