Roundtable: Is Jon Lester a Hall of Famer?

January 13th, 2022

, a five-time All-Star, won three World Series titles with two teams and is considered one of the most impactful postseason pitchers in modern history. But is he a Hall of Famer? In light of the left-hander’s announcement that he is retiring from baseball, a group of experts gathered to discuss his Hall of Fame candidacy.

•  Other HOF discussions: Helton | Andruw | Big Papi | Posey | Rolen | Wagner

Alyson Footer, editor/moderator: We'll start the way we always do, with a simple question. Is Jon Lester a Hall of Famer?

Mike Petriello, analyst: I think he's got a compelling case, especially when you give one billion extra points for helping to break the Cubs' curse. But no, he falls just short for me.

Jon Paul Morosi, and MLB Network reporter: I believe he's a Hall of Famer. His career reminds me of Mark Buehrle's, and I've voted for Buehrle twice.

Mark Feinsand, executive reporter: For me, he falls a little short. He was one of the best pitchers in his league in several seasons, but he was never the dominant ace that other teams feared. Great career, crucial piece of World Series teams, but not a Hall of Famer.

I have never voted for Buehrle, so that makes sense to me.

Sarah Langs, reporter/producer: Lester is such an iconic pitcher for two really notable franchises -- and in such successful years. But he falls short for me, too.

Morosi: We're at a time in the evolution of voting that the criteria for Hall of Fame pitchers is changing dramatically.

Petriello: I'm glad JP brought up Buehrle, because I agree that their cases are similar in a lot of ways, but Buehrle isn't getting in.

Feinsand: Lester seems like Mike Mussina-lite to me.

Morosi: I'll go back to my standard for the Hall of Fame: If I'm writing a one-page summary of the era in which the player competed, do I have to mention this player several times?

For me, with Lester the answer is yes. He beats cancer as a young pitcher and wins the clinching game of a World Series title for the Red Sox.

Feinsand: I’m not sure you would have to mention Lester OR Buehrle in a one-page summary of this era, JP.

His personal story is incredible. But beating cancer doesn’t get you into the Hall of Fame.

Petriello: I look at it as such: when I look at the truly elite aces of his era, is he among them? And I think my answer is ... no. He's in that next (very good, obviously) tier.

Morosi: He's a pivotal pitcher on one of the most charismatic teams of this century, the 2013 Red Sox.

And then he does that all over again with the Cubs three years later.

Langs: He seems to check all of the intangible and postseason boxes, I just think the actual production is a bit shy.

Petriello: He's also got a similar comparison to Andy Pettitte, right? Big-game pitcher, similar-ish kind of lefty. Pettitte threw more innings, and while I don't think this is a WAR argument, he has a much higher (FanGraphs) WAR. And I don't think he's getting in, either.

Feinsand: I like that comparison, Mike. I have voted for Pettitte because I think he deserves a deeper look in future ballots. With the ballot thinning out after this year, I think it’s possible I could vote for Lester five years from now for the same reason. Though the thinner ballot will help him.

Morosi: Two-hundred wins, five All-Star appearances, two titles with the Red Sox, a century-in-the-making title with the Cubs -- those are the credentials of a Hall of Fame pitcher. In the contemporary era, I should add.

Footer: I see how this group is leaning. But, could the three World Series championships push him over the edge? He played a significant role in all three. He also has a cumulative postseason ERA of 2.51, eighth among all pitchers in history with at least 10 starts.

That's something?

Morosi: The postseason numbers are absolutely critical. The Hall of Fame honors greatness. Lester was one of the best of his generation when it mattered most.

Petriello: I think postseason performance definitely matters, and his record is spectacular. It's something that'd push him over the edge for me if it was closer. I just can't see how he gets in when guys like Pettitte, Buehrle, [Tim] Hudson, Kevin Brown, potentially Cole Hamels won't be.

Feinsand: Lester’s postseason numbers are a huge factor. If he gets in, that will be the difference. To me, borderline candidates need to have a boost from the postseason. He certainly has that.

Morosi: This probably speaks to the way I view the Hall of Fame. To me, Cooperstown is a place to tell the story of baseball through the notable careers over time. Here's my question: Who best defined baseball history in the last 20 to 30 years?

On that score, Lester is ahead of Billy Wagner.

Feinsand: The Museum at the HOF tells that story for me, JP. The plaque gallery is a different animal.

Langs: Completely agree with that, Mark. He’s memorialized either way -- and the entire building displays the history.

Feinsand: But if I don’t necessarily believe Wagner should be in, then it’s a moot point.

Morosi: My take: Differences of opinion are a wonderful thing.

Petriello: I've never really bought into the "telling the story" idea, myself. You can't talk about the story of baseball without Roger Maris or Barry Bonds, and neither (for extremely different reasons, obviously) are getting into Cooperstown any time soon.

That puts too much importance on the Hall, a very flawed institution, really.

Morosi: Not surprisingly, I vote for Bonds ... and [Roger] Clemens ... but I will try to avoid traveling too far down this tangent!

Feinsand: Lester had some Hall-worthy seasons, for sure. But he had several that fell considerably short of that, too.

Footer: Here’s one factoid that I don’t think gets enough attention -- in an era where starting pitchers are often not permitted to go deep into games, Lester threw 200 innings or more in eight of nine seasons from 2008-16. He averaged 170 innings over his final five seasons, (not including pandemic-shortened 2020). Maybe that's not a Hall-worthy stat, but that's hard to do in today's era.

Petriello: Yes. That's incredibly impressive.

Morosi: And that describes one major reason why I vote for Buehrle. He threw more than 3,000 innings, with 14 straight years of 200 innings per season.

Feinsand: I’m a big innings-pitched guy, which was part of my Mussina case.

Morosi: Buehrle and Lester pitched with a longevity and excellence that should give us pause. I hope to vote for Wagner next year, when I have more space on my ballot. But I find it difficult to argue that Wagner's career (fewer than 1,000 innings) was more valuable or noteworthy than those of Buehrle or Lester.

Feinsand: I’m not against pause, at all. I think Lester is a rock-solid borderline guy. Please don’t read my arguments as a dismissal of him or that he’s not worthy of this conversation. I just believe he falls a tad short of Hall of Famer.

Petriello: I think there's one thing we can all agree on here, and that is this: hoooo boy did the Red Sox botch things by letting him go.

Langs: I know it isn’t all about numbers, and postseason numbers aren’t in most stat calculations -- but Lester’s numbers don’t get him to the point where that postseason part is enough to boost him. 34.6 peak 7-year WAR -- which is outside the top 164 in history. The workload is notable. That’s how he got 200 wins (the new 300, as Andrew Simon and I wrote about when he won his 200th). And he was good-to-great in those innings. But I don’t see quantity as the push-him-over-the-edge item either.

He’s so, so borderline. That’s why this is a fun conversation. And bringing in the intangibles which can determine these things really makes it intriguing. And I also want to note that I’m not knocking his career at all. An outstanding one, for sure. Just borderline for the end all, be all, HOF.

Morosi: I'm a big Hall guy, clearly, influenced in part by having attended and covered induction ceremonies in recent years.

Feinsand: David Cone’s career numbers are awfully close to Lester’s. He won a Cy Young, has five World Series rings. And he wasn’t close to making the Hall.

Langs: Cone seems like someone who would get far more consideration today -- that’s been on my mind lately.

Morosi: Seventy-five percent of the vote is a high standard, of course, but the institution needs to be refreshed by having new greats in that plaque gallery who bring people into the Hall and tell the story of the game. Lester does that.

Feinsand: I disagree. The institution needs the best players in the game’s history there. The fact that steroid-tainted stars aren’t being elected doesn’t mean that the next level of player from this era should be inducted.

Petriello: I just keep looking at this list of Lester, Hudson, Buehrle, etc. and having trouble seeing how he's ahead of them. I accept it doesn't account for postseason success, though he's not the only one of this group who had it. He just seems to be one of a group of starting pitchers who were very good but just short, and I'm the guy who wrote that the Hall is not inducting enough starting pitchers. Then again, that's why we have to wait five years. His career won't change in half a decade, but our perceptions might.

Morosi: And if you'd like to suggest that I'm somewhat swayed by Lester's achievements coming with teams like the Red Sox and Cubs ... well ... I am. These franchises have a particular significance to the game's history.

Mark, to borrow your words: Jon Lester is one of the best postseason players in the game's history. To go along with 200 regular-season wins and five All-Star appearances.

Feinsand: Lester wasn’t a part of the curse-breaking team in Boston, and he didn’t start a game in either of the first two rounds in 2007. He was a major part of '13, and obviously the '16 Cubs.

You’re absolutely right, JP -- which is why he’s a borderline candidate to me. Without the postseason resume, he would not be there in my eyes.

Footer: Last question: Will Lester eventually be elected to the HOF?

Petriello: Yes!

…By the Veterans Committee in 20 years.

Morosi: I concur with Mike! The writers won't elect him, but the Veterans Committee will.

Feinsand: I don’t think so. I think he stays on the ballot for all 10 seasons, but falls short, somewhere in the 40-50 percent range. He’ll have a better shot with the Veterans Committee.

Langs: I do think he will be -- the postseason part tends to really carry weight, but I agree it’ll be after the initial ballot and with the Era Committees.