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Should the Cubs re-sign Jon Lester?

My answer is a qualified yes.

Photo by Nuccio DiNuzzo/Getty Images

Jon Lester ranks as the best free-agent signing in Cubs history, and arguably the best in Chicago sports history.

The Cubs made the postseason in five of his six seasons in blue pinstripes. Despite a couple of rough years, his overall numbers as a Cub (3.64 ERA, 1.248 WHIP) were roughly comparable to what he posted in nine seasons with the Red Sox.

The Cubs owe Lester $10 million for 2021; that’s a buyout that wouldn’t count against the luxury tax. (There’s also an option for $25 million that they almost certainly wouldn’t exercise).

It’s clear that Lester’s talents aren’t what they once were. When he came to the Cubs he brought a 92 mile per hour fastball, on average. Per Fangraphs that’s dipped under 90 for the 2020 season, to 89.2. With the dip in velocity Lester has relied much more on a cutter which still hits 87.5 miles per hour, not too far off his career peak.

While Lester’s 2020 season appears poor at first glance, check these numbers out:

Lester vs. White Sox: two starts, 7⅓ innings, 18.41 ERA, 2.455 WHIP, five home runs
Lester vs. all other teams: 10 starts, 53⅔ innings, 3.35 ERA, 1.174 WHIP, six home runs

Clearly, teams with a lot of righthanded power like the White Sox trouble Lester at this stage of his career. But against other teams, Jon was still the pitcher he has been over the last several seasons.

Which is why I’d bring him back for another year, or possibly two. Having had his “generational money” contract, plus the $10 million buyout for 2021, Lester might be willing to settle for less money to stick around a place where he’s comfortable. He even said as much:

The Cubs didn’t do another “2016” in 2020, but it seems clear Lester wants to return to the Cubs. And it appears the Cubs would like to have him back:

Jon Lester “the person” could be important to the Cubs, too. Beyond Yu Darvish, Kyle Hendricks and probably Alec Mills, no one is a lock for the Cubs rotation in 2021. Jon Lester, I believe, can serve the Cubs well in a fifth-starter role, and perhaps be a mentor to younger pitchers.

A two-year, $15 million deal might get it done. Or, if that seems too much for the 2021 budget, make it one year, $8 million with a $7 million team option that vests if Lester makes benchmarks such as 30 starts (something he did for 12 consecutive seasons before 2020 intervened).

Would you bring Jon Lester back?


Should the Cubs re-sign Jon Lester?

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