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Emotional Jon Lester ponders uncertain future with Cubs: ‘I didn’t think six years would go this fast’

2 years agoTony Andracki

As the Cubs marched to their fourth straight win and second straight walk-off victory Wednesday night, Jon Lester quietly walked off the Wrigley Field mound for what may have been the final time.

The 2020 Cubs are in the midst of a pennant race and there’s plenty to focus on with the postseason just around the corner.

But the gravity of the moment wasn’t lost on Lester, who pitched 5 innings in Wednesday night’s 3-2 Cubs win over the Indians.

“I think maybe I was trying a little bit too hard tonight,” Lester said after the game, choosing his words carefully. “There’s some things weighing on my mind that led into tonight. So maybe the effort was a little bit too much. Trying to go out there and maybe being a little bit too perfect, I don’t know.”

Lester elaborated on those thoughts weighing on his mind, admitting he felt a lot of emotions and really wanted the night to go well.

The veteran southpaw has an option in his contract for the 2021 season, but he will turn 37 in January. The Cubs have just three home games left at Wrigley Field this weekend before hitting the road to close out the regular season.

As of right now, the Cubs would host a team for the Wild-Card round of the playoffs at Wrigley Field, but there’s no guarantee Lester would see action in those games with Yu Darvish and Kyle Hendricks firmly atop the rotation.

“Hopefully not the last regular season start,” Lester said. “This year hasn’t been easy for a lot of reasons and I’m not sitting here saying, ‘woe is me,’ because there’s a lot of people worse off than me.

“But a lot of emotions coming into this. Don’t really know what to say, how to take it. A lot of uncertainties going forward.”

Lester is putting the finishing touches on his sixth year with the Cubs after inking a $155 million contract prior to the 2015 season. He spent the first nine years of his career with the Boston Red Sox before being traded to the Oakland A’s midway through the 2014 season.

He admitted that while he wanted Wednesday night to go smoothly, there was always going to be a weird feeling cast over the evening without fans inside Wrigley Field.

“I think that’s probably the most frustrating part for me,” Lester said. “Going back to ’14, I didn’t really get to walk off the field like I wanted to at Fenway. Obviously tonight didn’t go quite the way I wanted to, having an empty stadium. Not really how I envisioned possibly my last start here.

“Like I said, I’m not going to sit here and say, ‘woe is me.’ But I didn’t think six years would go this fast.”

Nobody can predict how the future will go with Lester and the Cubs, but there is no denying the fact he changed this franchise forever. He joined a team that was coming off an 89-loss season and last-place finish and led the 2015 Cubs to the NLCS.

Lester’s signing helped set in motion the organization’s turnaround as his presence brought in David Ross and coupled with Joe Maddon’s hiring, those three led the charge in creating a winning culture.

“Jonny’s a pro, the way he goes about it,” Jason Heyward said. “We all play this game because we love it. We all play this game to compete, to win. And he embodies that. Anything else could be going on in the world, but when you step in between those lines, you go out there and give it your all to get a W for your team. And that, to me, is Jon Lester.

“Him out there on that mound, battling his ass off, doing that for this city, changing the culture, coming in and taking the leap of faith that they were going to do what they said they were going to do and put the pieces around him and continue to get good, continue to go win. Says a lot about a man trusting in himself and trusting in the organization.”

Nobody could forget Lester’s legendary 2016 campaign, where he finished second in NL Cy Young voting, earned the NLCS co-MVP with Javy Báez and then turned in an incredible performance in the World Series, including a gutsy appearance out of the bullpen in Game 7.

“A tip of the cap for Jonny and hopefully he keeps throwing the ball,” Báez said. “I don’t know what’s going to happen with him next year, but obviously we love him here and he did a lot for us.”

Heyward understands what Wednesday night meant to Lester and even though the future is yet to be written, Heyward knows the Cubs had to acknowledge that it could’ve been the last Wrigley Field appearance for the veteran lefty.

“This dude’s been a rock here,” Heyward said. “We can’t not do it. Gotta show him some love, gotta show him some respect and we hope we can do a lot more for him here in the near future.”

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