Retirement party: Chicago owes Jon Lester a tall one


Among the memorable comments made by Cubs officials and Jon Lester in the aftermath of the pitcher’s seismic free agent signing with the Cubs seven years ago, one in particular comes to mind as the big left-hander formally retired this week:

“I’m not here to screw around.”

Lester said that during his introductory news conference in December 2014 — the same day team president Theo Epstein swore he would have “soaked myself in deer urine” to close the deal for the avid hunter and six days after manager Joe Maddon said the Cubs “won the baseball lottery” by landing Lester.

But for all the champagne-soaked scenes that quickly overtook the visions of deer urine and for all the jackpots the Cubs cashed with that winning ticket during Lester’s six history-making seasons with the Cubs, it’s that simplest of statements that said the most about the pitcher and teammate Lester became.

If not the imprint he left on an organization that had been a laughingstock for much of the century before that stretch — an imprint that helped create the kind of expectations that has a fan base largely fuming these days after ownership triggered a selloff of core players and launched a new rebuild as soon as the door hit Lester on the way out of Wrigley.

Lester’s response to the Cubs’ unwillingness to bring him back on the steeply discounted deal he offered a year ago: the highest of Chicago high roads.

He opened his credit card at several watering holes and bought the city a round.

Who does that?

“It ended up being an awesome, awesome thing,” Lester said on Wednesday’s Cubs Talk Podcast, adding he’s run into many since then who took him up on the beers that day “and actually bought me a beer later down the road.”

Talk about making an impact. And building relationships. And not screwing around.

Maddon at his introductory new conference at the Cubby Bear in the fall of 2014 struck a similar tone when he offered to buy the assembled media a shot and a beer. But the bar was closed.

Lester actually did it.

Which might as well be the epitaph on a 16-year career that included five All-Star selections and three rings. It certainly sums up the Chicago chapter of that career.

Just how well did he deliver on the promise of replicating what he had done in Boston after getting to Chicago?

His winning percentage and ERA in nine seasons in Boston was .636 and 3.64.

In six seasons in Chicago: .636 and 3.64.

The six seasons in Chicago also produced a World Series championship and two top-10 Cy Young finishes — same as his previous six seasons in Boston — with more playoff berths (five) and as many winning seasons (all six) as Boston had in his nine years there.

Jake Arrieta produced a season for the ages in 2015, and backed it up with an All-Star performance in 2016. Kris Bryant was the Rookie of the Year in 2015 and MVP in 2016. Anthony Rizzo was an All-Star, Javy Báez a breakout defender and postseason performer, Dexter Fowler an igniter at the top of the order, Kyle Hendricks an ice-cool, big-game performer.

But Lester made it happen. His signing was the start of everything the Cubs did during a six-year run that was unlike any in franchise history, the signing that provided the credibility that made others believe in the talent and fortunes of what was a last-place team at the time.

“I wouldn’t be here if I didn’t think they were going to win in 2015,” Lester said during that introductory news conference.

“I don’t like to lose.”

Maybe that’s the epitaph today.

Whatever the exact words etched on that career marker, the impact of Jon Lester in the Cubs’ clubhouse for six years was bigger than anyone else who came or went during that time — or since. That much has become even more clear in the palpable deficit his departure left behind during a 2021 season derailed by flawed starting pitching and distractions even before the nine-man purge at the trade deadline.

As Lester looked back on what they built in Chicago before that teardown, he pointed to the expectations that fans now have for the Cubs and suggested another long rebuild won’t be tolerated.

“You’ve given them a taste of winning; they expect winning,” he said during a conversation with NBC Sports Chicago in Washington an hour or so after the Nationals traded him to the Cardinals.

“I don’t think it’s going to be like the five-year rebuild again. I think they’re going to be right back in it,” he said then, perhaps foreshadowing the Marcus Stroman, Wade Miley and Yan Gomes acquisitions. “You always know Chicago’s going to make money, so it’s just up to the organization on how they want to build that.”

Of course, that’s been the issue, if not the problem, during these past two seasons: Ownership’s decision-making/cost-cutting.

Whatever direction the Ricketts family allows from this point forward, and whatever Epstein’s successor Hoyer does within those parameters, Lester certainly has done his part during what might be the most historically significant chapter in a decorated and storied career.

“I remember a conversation I had with [Anthony Rizzo] back in ’15 when I first got there,” Lester said on the podcast Wednesday. “I was like, ‘It’s all fun and games until you get expectations. When you get expectations, now you’re relied upon to produce.’

“I wouldn’t have it any other way in a season. Look at the Cubs in previous years: Their expectations were to finish last and lost 90 to 100 games. That sucks. Now you flip it to, ‘We’re expected to win the division every year.’ Now it comes with accountability, and you’ve got to show up to work every day and put a product out there,” he said.

“When you get booed because you stink, you should. That’s part of it.”

Few have brought the expectations, backed them up, answered for the moments worth booing and raised those around him in the Cubs’ clubhouse like Lester did in his six years there — even if teammates might have initially “thought I was an asshole.”

Fewer still have won in Chicago like he has.

“The best way to play is with expectations, because those 162 games, if you’re doing it for nothing, are the most miserable dang things that you’ll ever play,” he said.

Whatever becomes of the Cubs next and whatever Lester does for a next chapter in his life, one thing seems certain around here:

Chicago owes this man a round.

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