NEWSLETTER
You could point to a lot of seminal moments over the past nine years of the Chicago Cubs’ story arc, so I won’t go hyperbolic and say the Jon Lester signing was THE SINGULAR MOMENT where everything changed, but I can tell you it was the first “holy shit I think things might actually be different” moment for me.
It was the Winter Meetings back in 2014, and the new Cubs front office was rumored to be into all kinds of maneuverings, including trying to land one of the biggest starting pitcher free agents in recent memory, Jon Lester. The team was coming off a really great second half of 2014, though, in those days, that meant they were close to .500 for half a season. But it was a young, up-and-coming group, and they’d also just landed Joe Maddon to be the new manager. It didn’t feel crazy that the Cubs could actually get Lester, but it certainly had been a long, long time since the Cubs landed a free agent like that. It took the Tribune’s spending binge in advance of the sale of the team to land Alfonso Soriano, and before that it was … Moises Alou? Does a three-year deal for an older outfielder even count as a huge free agent signing?
That is all to say, even as we saw the corner turning, it wasn’t until the Cubs actually sealed the deal with Lester that we knew just how hard they were pushing for 2015 and beyond. That 1 am signing was one of my favorite Cubs moments.
And, of course, the front office was justified in its massive outlay of cash, just as we were justified in being so excited by the move. In Lester’s first three years with the Cubs, they reached the NLCS all three times, winning a World Series in the middle largely on the strength of Lester’s exceptional postseason performance.
The next three years were less noteworthy, both for Lester and for the Cubs, but he was still mostly a solid starting pitcher. A veteran you were pleased to have at the back of your rotation, and extremely happy to have in your clubhouse.
To that end, at his season-ending press conference, Cubs President Theo Epstein was naturally asked about the future of Lester and the Cubs, given that this was the final year of his six-year, $155 million contract.
Epstein said that the two had already exchanged texts, and planned to meet this week to discuss things.
“It remains to be seen whether Jon has pitched his last game as a Cub or not,” Epstein said. “There’s certainly the possibility that he continues to call Wrigley Field home.”
Epstein later discussed the need to add some pitching, given that Yu Darvish and Kyle Hendricks are the only guys absolutely set in the 2021 rotation at the moment (though he did praise the development of Alec Mills and Adbert Alzolay this year). It was never inconceivable that the Cubs and Lester would want to re-up on a modest deal for 2021, though I tend to think the pandemic and the financial fallout complicate things. Guys in Lester’s tier, I suspect, are going to have a difficult time finding sizable guarantees, which would mean the Cubs may want a reunion only in the event that Lester finds nothing else suitable out there and simply wants to keep pitching.
So, then, the two men will talk, and I expect they will put their cards on the table, and Lester can set about seeing what’s what in free agency, and ditto the Cubs. Maybe they find each other at the end of that process, maybe they don’t. For his part, Lester has certainly seemed open to sticking with the Cubs.
In the meantime, Epstein made sure he pointed out the importance of landing Lester, and what he’s meant to the organization.
“Whether he leaves or stays, this is an appropriate time just to acknowledge the profound impact he had on our organization,” Epstein said of Lester. “It’s rare when somebody joins an organization with some clear goals in mind: to win a World Series, to change a culture, to show up in October just about every year and pitch really well in big games, to be a great teammate, to be somebody our organization can be proud of, to make an impact on his teammates and community. He accomplished all those goals in such an honorable manner. We owe him a great debt of gratitude.
“We were investing in Jon Lester the person every bit as much as we were investing in Jon Lester the pitcher,” Epstein continued. “He came through in both areas for us in typical Jon Lester fashion. Huge tip of the cap to him.
“He’s made a huge impact on Chicago Cubs baseball and it remains to be seen what the future holds, but he’s somebody I really admire and always will.”
