Imagine a baseball legend, a storyteller, and a true team player all rolled into one. Meet Jon Lester, a pitcher who's not just about the numbers, but about the heart and soul he brings to the game.
In a world where baseball is more than just a sport, it's a story, and Lester is its leading man. His journey, from the locker room to the retirement stage, is one of dedication and impact.
The Legacy of Jon Lester: A Hall of Fame Journey
Lester, now happily retired, has a unique way of engaging with reporters. He plays hard to get, but once he starts talking, he shares his heart and mind, leaving no question unanswered.
This man is not just a baseball player; he's a master storyteller, a beloved teammate, and a pitcher whose skills have left an indelible mark on the game.
We caught up with him at the Cubs Convention, where he was inducted into the Cubs Hall of Fame, alongside fan favorite Jody Davis and the late broadcaster Vince Lloyd. Earlier, he was elected to the Red Sox Hall of Fame. It's been five years since he retired, but his impact is still fresh in our minds.
When asked about his induction, Lester was speechless at first. But then, true to form, he opened up, sharing his thoughts for a solid half-hour in front of the cameras and continuing with reporters for another 15 minutes.
Being inducted into a regional Hall of Fame is an honor, but it's not the ultimate recognition. The real test will come with the National Baseball Hall of Fame election, and Lester is on the clock. He'll be on the ballot next season, and while he might not make it on the first try, he's at the heart of a debate about what defines a Hall of Famer and what constitutes a great starting pitcher.
On the night of our interview, Lester wore one of his three World Series rings, a massive Cubs ring that's a testament to the magical 2016 season. He joked that his Boston rings are now too tight, a lighthearted moment amidst the seriousness of the occasion.
Lester's postseason performances for both the Cubs and the Red Sox are a significant part of his legacy. When asked about it, he seemed surprised, almost unaware of the impact he had.
"I don't know about the Hall of Fame," he said. "I was just lucky. My kids don't remember much, so we've been down some rabbit holes, reminding them that their dad was pretty good. I started thinking, how many years didn't we make the playoffs? I think it was two or three out of my 16-year career. If that gets me into the Hall, great. If not, I'm happy driving the carpool every morning."
The actual number of seasons without a playoff appearance is four: Boston missed from 2010-12, and the Cubs missed in 2019.
Over his career, Lester pitched in 26 playoff games with 22 starts, throwing 154 innings with a remarkable 2.51 ERA and a 1.019 WHIP. In six World Series games, he went 4-1 with a 1.77 ERA. With Boston, he compiled a 2.11 ERA and 1.043 WHIP in 13 games. With the Cubs, he had a 2.44 ERA and 0.957 WHIP in 10 starts and two relief appearances.
Only 10 pitchers in MLB history have pitched over 150 innings in the postseason, and Lester has the lowest ERA among them.
Lester is more than just numbers. He's the guy who could pitch seven innings on a hot summer day and deliver in the cold of October. In 2016, when the Cubs needed him most, he exceeded expectations, going 19-5 with a 2.44 ERA during the regular season and improving in the postseason, where he went 3-1 with a 1.93 ERA in five starts.
He pitched eight scoreless innings in the Cubs' first playoff game that year, a 1-0 win over the Giants, and gave up just two runs in 13 innings in the NLCS against the Dodgers, earning him co-MVP of the series.
In the World Series, he lost Game 1 but came back strong in Game 5, pitching six innings of two-run ball in a must-win game. In Game 7, he came out of the bullpen with a 5-1 lead, walked a batter, gave up two runs on a wild pitch, but settled down to pitch the sixth, seventh, and into the eighth.
The Cubs won the World Series that year, ending a century-long drought. Game 7 was Lester's last playoff victory, but it was a memorable one.
Winning the World Series with both the Red Sox and the Cubs is a significant achievement, and it will likely help his case for induction into Cooperstown.
"Getting inducted into the Cubs and Red Sox Halls of Fame means a lot to me," he said. "The Red Sox organization values what I did, and that means a lot. It's like the cherry on top of my sundae. I've got my sundae built with my time here and with the Red Sox. If I get that call for Cooperstown, that's the cherry."
Lester downplayed the importance of recognition, saying he played for the love of the game and the competition.
"I didn't play for the Hall of Fame," he said. "If I get the call, I'll be the happiest guy in the world. But if I don't, it won't change how I feel about my career."
Lester knows he's part of a dying breed, the 200-inning starter, a role that's being devalued in today's game. Hall voters are modernizing how they value starting pitchers, and while Lester's stats might not have cut it a generation ago, they will now.
"When I came up, guys like Curt Schilling, Josh Beckett, and Tim Wakefield set the standard. If we didn't go six innings, it wasn't a good start. Now, they're saying just get 12 outs. Twelve outs was our long reliever when I played. The game has changed, and I don't like it. I'd rather watch a starter grind and sweat to get a guy out in the seventh or eighth inning than watch a guy get 12 outs and sit in the dugout happy."
Lester always wanted more responsibility, whether it was on the mound, in the clubhouse, or paying the bill at team dinners. When he signed that $155 million deal with the Cubs, he felt the pressure, but he delivered, outperforming his contract over the next six seasons.
This coming season, Lester will be honored at both Fenway Park and Wrigley Field, two iconic baseball stadiums. And in the next decade, we hope he'll be in Cooperstown, giving a speech, pretending he doesn't know what to say, just as he did when he was inducted into the Cubs Hall of Fame.
But here's where it gets controversial... Do you think Lester's legacy is enough to secure his place in Cooperstown? Or is it just a nice story? Let us know in the comments!
