Greenberg: Lester’s next induction should be in Cooperstown

Posted January 25, 2026 5:05 pm

By Jon Greenberg

Now happily retired from baseball, Jon Lester still does this thing where reporters ask him if he has a few minutes and he puts on a little act like he doesn’t want to do it and then he goes on to talk until you run out of questions.

Lester is one of baseball’s best storytellers, along with being one of the best teammates and, most important, one of the best pitchers of his generation.

We talked to Lester on Friday night at the Cubs Convention, after he was announced as a 2026 inductee to the recently created Cubs Hall of Fame, along with 1980s fan favorite Jody Davis and the late broadcaster Vince Lloyd. Earlier in the month, he was elected to the Red Sox Hall of Fame. He is entering his fifth year of retirement, but it seems like just yesterday I was hanging around his locker looking for him to fill my notebook.

What did he think about being a Cubs Hall of Famer?

“Right now, I don’t have words for it,” Lester said before he went on to talk for about a half-hour in front of the cameras and then for another 10 to 15 minutes with a group of reporters, while his two sons waited politely for him to finish.

A regional Hall of Famer is not unlike being a local Emmy winner. It’s something to be proud of, but not quite the real thing.

After Tuesday’s National Baseball Hall of Fame election, though, he is now on the clock for the big induction, not a regional one. He will be on the ballot for the first time next season.

He won’t be a first-ballot guy, but he’ll be at the center of evolving debates about what makes a Hall of Famer and what voters will do with the changing paradigm of what constitutes a HOF-worthy starting pitcher. My colleague Tyler Kepner, a future Hall of Famer himself, wrote about these interconnected conversations, specifically regarding Cole Hamels (23.8% of the vote) and Félix Hernández (46.1), in a recent column.

When we talked to him on Friday, Lester was wearing one of his three World Series rings, the gaudy Cubs one that’s about the size of a boulder, in honor of the 10th anniversary of that magical season. The 42-year-old joked that the two from Boston (from 2007 and 2013) are now too tight.

I was curious if Lester thought his postseason performances for the two clubs could help his cause to get into Cooperstown. He seemed surprised someone went there.

“Oh, I don’t know about the Hall of Fame,” he said. “I know that I was very fortunate. I was just telling somebody on the way over here, my kids don’t really remember a lot. And so we’ve gone down some rabbit holes of like, hey, your dad was actually OK. And so I got to thinking one night, I was like, how many years did we not go to the playoffs? I think it was two or three. My whole career, 16 years. At the end of the day, if that gets me in the Hall of Fame, cool. If it doesn’t, I’m happy driving carpool every morning, dropping them off.”

The actual answer to the number of seasons that didn’t end in the postseason is four. Boston missed the playoffs from 2010-12, and the Cubs missed it in 2019.

Over his career, Lester pitched in 26 playoff games with 22 starts. He threw 154 innings in those games with a 2.51 ERA and a 1.019 WHIP. In six World Series games (five starts), he went 4-1 with a 1.77 ERA. In 13 playoff games (11 starts) with Boston, he compiled a 2.11 ERA and 1.043 WHIP. With the Cubs, he made 10 starts and two relief appearances, putting up a 2.44 ERA and 0.957 WHIP.

Lester is a pitcher who transcends numbers, though he did finish his career with an even 200 wins. He was the guy you counted on to go seven innings on a hot July afternoon and on a cold October night. And in 2016, when he was needed the most, he was everything the Cubs paid for in free agency and then some.

During the regular season, he went 19-5 with a 2.44 ERA. And he got better in October as the Cubs won four of his five postseason starts. In those starts, he went 3-1 with a 1.93 ERA, throwing 32 2/3 innings, while striking out 26, walking five and giving up 24 hits. He pitched eight scoreless in the Cubs’ first playoff game that year, a 1-0 win over Johnny Cueto and the Giants, and gave up two runs in 13 innings in the NLCS against the Dodgers, helping him earn co-MVP of the series.

He lost Game 1 of the World Series with a so-so start but pitched six innings of two-run ball in a must-win Game 5 at Wrigley. And then, in Game 7, he came out of the bullpen with a 5-1 lead and a man on base. He wound up walking a guy and giving up two runs on a wild pitch, but he settled down and pitched the sixth, seventh and into the eighth.

The Cubs won, famously, in 10 innings, ending a drought over a century long. Game 7 wound up being the last playoff victory that Lester pitched in, though not for lack of effort. He gave up just one run in each of the three games he started in 2017, but the Cubs lost every game. He gave up one run in the 2018 wild-card game, which the Cubs lost to Colorado 2-1 in 13 innings. That turned out to be his playoff finale.

Winning the World Series with both the Red Sox and the Cubs, I believe, will help his cause with the baseball writers who vote for Cooperstown and baseball immortality.

“To me, getting this tonight and getting the Red Sox is, I don’t wanna say more important to me, ‘cuz it’s not,” he said. “But it means more to me because this organization, the Red Sox organization, value what I did.”

He continued, “At the end of the day, the Hall of Fame for me is getting that cherry on the top on your sundae. I’ve got my sundae built right now, being a part of this and the Red Sox. If I get that call, that’s the cherry, you know what I’m saying?”

Lester downplayed the importance of getting his recognition.

“I didn’t play the game for that,” he said. “I played the game because I loved it. I played the game because I love to compete. I played because it was fun. I know it didn’t look that way sometimes for me when I was out there, but I just loved the competition. I loved the cat-and-mouse game of pitching. … If that call comes, I’ll be the happiest SOB in the world. Don’t get me wrong. But if it doesn’t come, it doesn’t change how I feel about my career.”

He knows he was part of a dying breed, the 200-inning starter, the horse you ride into the seventh inning every five days. Hall voters (and I’ll finally be one next year) are modernizing how to value starting pitchers in a modern age. Lester’s stats might not have gotten him in a generation ago, but I think they will now.

“The way I came up, I came up with Curt Schilling, Josh Beckett, Tim Wakefield, and these guys were like, if we don’t go six innings, it’s not a good start,” he said. “You give up zero, you give up five, it doesn’t matter. You get a win, don’t care. If I don’t get into the seventh inning, it’s not a good start.”

Needless to say, he’s not a fan of a game where starting pitchers are devalued and pitchers in general are referred to as “out-getters.” He threw 2,894 innings between the regular season and the playoffs.

“Now, they’re going, ‘Well, just get 12 outs,’” he said. “Twelve outs? That was our long reliever when I played. But the game’s changed. I don’t want to take anything away from anybody and what they’re doing — they’re obviously throwing harder. The game’s different in that aspect. At the end of the day, I think starters, it’s kind of like defense and football. Starters win championships. Once again, that’s been proven wrong with the Dodgers and other teams. I’m biased because I was a starter, but I think that you build your team on starting pitching and then you win games based on the back end of your bullpen.”

Obviously, there are valid reasons for the shift in thinking, and it stems from teams having databases of actual information. If you want to win, you do what’s best for the team, not the pitcher’s feelings. But it’s also a lot more enjoyable to watch a starter grunt and sweat and get out of a jam. There’s a human element that is lost. An entertainment angle, as well.

“I don’t like it, but it’s today’s game,” he said. “So it is what it is, you’ve got to just deal with it. It’s not fun to watch, because I’d rather sit there and watch the starter go figure out how to get a dude out in the seventh or eighth inning with 120 pitches than watch a guy get 12 outs and sit in the dugout and be happy about it, right? Which they’re happy about because that’s what they’re asked to do.”

Lester always wanted more responsibility, whether it was on the mound, in the clubhouse and when the check came for team dinners. When he signed that $155 million deal with the Cubs, he struggled at first, and I remember talking to him about the pressure he felt and how he learned to get past it.

He was so important to the Cubs’ rebuilding plan that when he signed before the 2015 season, I asked Theo Epstein what he would’ve done to close this deal. Would the Yale grad have gone into a hunting blind with Lester?

“I was ready to soak myself in deer urine, if necessary,” he said.

He didn’t need to do that, but Lester wound up outperforming that contract over the next six seasons. When it mattered most, he was a player that you counted on. More times than not, he delivered. And when the check came, he paid it.

This coming season, Lester will be honored at both Fenway Park and Wrigley Field, two historic cathedrals of baseball. And sometime in the next decade, I hope he’ll be giving a speech in Cooperstown, feeding us a white lie that he doesn’t know what to say.