Cubs Insider

Lester feels emotional weight in final home start as a Cub

Cubs Insider

If the emotions weren’t evident in the five-pitch walk to open the game, they were unmistakable in Jon Lester’s face and in every word he spoke late Wednesday night, even from the social distance of a Zoom session with media.

“I didn’t think six years would go this fast,” said the longtime Cubs ace, who might have made his final Wrigley Field start of a storied Cubs career.

Lester, who was coming off an impressive bounce-back start in Milwaukee, battled through five shaky innings before giving way to the bullpen in a 3-2, 10-inning victory over Cleveland -- maybe the most poetic of opponents for such a finale.

“I think maybe I was trying a little bit too hard tonight,” said Lester, who made his 92nd career start at Wrigley Field — 91st since signing that six-year, $155 million free agent deal that turned the tide of a franchise.

“There’s some thing weighing on my mind that led into tonight,” he added. “Maybe the effort was a little bit too much, trying to go out and maybe be a little bit too perfect, I don’t know.”

He certainly didn’t know it would look like this at what might the final stretch of his Cubs career, a 15th year in the big leagues like nobody before this year has experienced, from the pandemic shutdown to midsummer restart, COVID-19 protocols and not a fan in sight.


“I think that’s probably the most frustrating part to me,” said Lester, who still gets chapped when he thinks about how his original team, the Red Sox, unceremoniously traded him at the deadline in 2014 after extension talks failed — then called during the winter but offered nothing close to a competitive bid during his free agency.

“I didn’t get to walk off the field like I wanted to at Fenway,” said Lester, who helped win two championships in Boston, “and obviously tonight didn’t quite go the way I wanted to, with an empty stadium.”

His voice was flat and dimmed at times as he spoke.

“It’s not really how I envisioned possibly my last start here,” he said.

His first-year manager didn’t envision being the one who would take the ball from him in that start after only 62 pitches, certainly not all those years they were teammates, when Ross was Lester’s personal catcher and close friend.

“That’s a tough one as a manager and pulling a buddy out with a low pitch count,” said Ross, who’s managing for a division title in the final 12 days of the season and played the percentages in a 2-2 game of a fresh bullpen against five innings of hard contact and a third time through the Cleveland lineup.

Regardless of that moment or any other during this short, surreal season, Lester already has earned a lasting place in Cubs lore during six seasons that included two of his five All-Star appearances, a Cy Young runner-up finish, a National League Championship Series MVP, 76 regular-season victories, a 2.44 ERA in 10 postseason starts (and a huge Game 7 relief appearance in Cleveland), and a career-topping championship for the ages.

“You get to the postseason, and it’s a whole ‘nother league,” said Jason Heyward, a teammate for the past five seasons. “And him out there on the mound battling his ass off doing that for this city, changing the culture, coming in and taking a leap of faith that they were going to do what they said they were going to do and put the pieces around him to get good and to go win says a lot about a man trusting in himself and trusting in an organization.

“This dude’s been a rock here.”

Lester, 36, won’t reach the vesting requirement for a 2021 option that now becomes a $25 million club option (or $10 million buyout).

Lester sounded like a pitcher who wants to return, and teammates want him back. But it’s unclear how many of those teammates will be back during a time of massive economic uncertainty for a roster that already had tapped the front office’s payroll budget the last two years.

Nobody knows that more than Lester.

“We don’t know what the future holds, so there were a lot of emotions going into tonight,” he said.

“This year hasn’t been easy for a lot of reasons, and I’m not going to sit here saying, ‘Woe is me,’ because there’s a lot of people worse off than me,” he said. “But just a lot of emotions coming into this, and I don’t really know what to say, how to take it, a lot of uncertainties going forward.”


It makes for a bizarre finale to a story that began when Lester signed with a last-place team to lend credibility to a fourth-year effort to build a new competitive window for the Cubs.

It’ll be six straight winning seasons with the Cubs’ next victory and is all but assured of being the Cubs’ fifth playoff season with Lester.

With almost nothing else assured beyond that.

“I’m not going to shy away from it: This could be our last year together, and I think we all know that,” Anthony Rizzo said last month of an extra motivation that has driven many in the clubhouse this season.

For Lester, it might mean one more start at Wrigley if the Cubs reach Game 3 in a best-of-three first round. After that, it’s off to the Texas playoff bubble even if they keep winning.

RELATED: How Cubs, White Sox can make case for their own playoff bubble

For teammates, Lester offers one more personal incentive into October.

“We’ve got to show him some love, got to show him the respect,” Heyward said, “and we hope we can do a lot more for him here in the near future.”

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