Cubs Insider

The one pitcher the Cubs should sign this winter: Jon Lester

Cubs Insider

With 60 percent of their veteran starting rotation cycling out of their contracts, the Cubs almost certainly will be forced to go outside the organization for one or more starting pitchers for 2021.

If they do it right, they won’t have to go far for at least one:

Just bring back Jon Lester.

Of course, it makes no sense because he’ll be 37, has struggled much of this season after fighting through one of his worst seasons last year and as recently as Wednesday was lucky to give up only two runs in five innings as hard as Cleveland hitters were on his stuff.

It also makes too much sense not to do it.

As recently as a week ago, he shut down the Brewers for six innings after making between-starts adjustments, has as much velocity and ability as he did two years ago when he made his fifth All-Star team and remains the toughest-minded, most competitive pitcher on the staff, if not every player on the team.

“I remember his press conference like it was yesterday,” teammate Anthony Rizzo said of the December 2014 introduction after signing a six-year, $155 million deal. “One of the main things he said was, ‘I’m coming here to win.’ And that’s coming to a 90-plus-loss team in 2014.

“And we turn around to win 97 games and win division after division, NLCS, NLCS, World Series — he came here to win, and that’s just what he’s done.”


Every pitcher has a shelf life.

And some pitchers, such as Lester, have a $25 million price tag attached to a club option for next year.

So that’s not going to happen. The Cubs will pay the $10 million buyout instead.

But there’s a lot of conversation available in between.

In an uncertain baseball economy and a tough recent track record to sell on an open market, Lester’s best bet on a short-term, low-cost deal might be right back in Chicago.

It’s definitely the Cubs’ best bet if they can get him.


Are you going to bet against Lester? Bet against a guy whose ERA is more than a full point better in 26 postseason games in his career than the regular season — including 1.92 in his last 10 postseason games for the Cubs?

Bet against him having value on what might be an incentive-heavy contract for one more year?

Lester got emotional after Wednesday’s start, acknowledging the likelihood it was his final start at Wrigley Field as a Cub.

MORE: Jon Lester shows emotional weight of final home start as a Cub

His manager and former personal catcher got emotional two days later just talking about that night and taking the ball from Lester after the fifth inning with a low pitch count.

“Probably the hardest pull that I’ve had. My stomach was in knots, knowing I had to go tell him he wasn’t going back out after the fifth,” Ross said. “I know what this guy’s meant to this franchise. I know there’s nobody that’s done more for me in my career than that human being and what he’s done for me and my family. …I wouldn’t be sitting in this seat without that guy.”

Teammates from Rizzo to Javy Báez to countless pitchers in the clubhouse also talk about Lester’s “generosity,” influence on young careers and team-building character. The front office has known him since he was a teenager in the Red Sox farm system and became much closer to him and his family during his harrowing battle with cancer a few years later.

Picture Lester not only as a competitor for a team that can still open a season with Yu Darvish and Kyle Hendricks next season — but also as an influence for the Adbert Alzolays, Brailyn Marquezes and other young pitchers (and hitters) during what’s sure to be a season of transition next year.

Then picture the mood this week with the thought of his six-year run at its end.

“I look at things through a different lens,” Ross said. “I don’t see [Wednesday] as his last start here. I see him coming back. That’s my hope.

“I think he’s got a lot more to prove. I think he’s got a lot more to do in this game.”

We already know he came here to win.


In fact, with Friday’s 1-0 victory over the Twins behind Hendricks’ impressive start, the Cubs clinched their sixth winning season in Lester’s six years in Chicago.

Don’t think he could help do it again?

Don’t bet against it.

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