Jon Lester To Red Sox? Whether Reunion Makes Sense For Either Side

Could the longtime Red Sox star return to Boston?


November 20, 2020

Will the Red Sox make a splash this offseason? Boston has financial flexibility and a strong desire to bounce back from a disappointing 2020. As such, we’ll examine whether several notable free agents make sense (or don’t make sense) as the club looks to retool for 2021 and beyond.

Baseball reunions often work better in headlines than they do in actual practice.

But could a genuinely worthwhile reunion be in the cards this offseason for Jon Lester and the Red Sox? It’s a storyline that’s impossible to ignore.

By now, you know Lester’s backstory: Eight-plus seasons, including two championships, in Boston, a mid-season trade in 2014 to the Oakland Athletics and then six campaigns, including another World Series title, in Chicago with the Cubs. The Tacoma, Wash., native, whom the Red Sox selected in the second round of the 2002 Major League Baseball draft, has had a fantastic career. He might be a Hall of Famer.

And now, at 36 years old, he’s a free agent. The Cubs bought out the final year of Lester’s contract, and though there’s been some talk of the veteran lefty returning on a cheaper deal, the general consensus seemingly indicates Lester and the rebuild-bound Cubs will part ways.

So, should the pitching-starved Red Sox pursue Lester? It’s complicated.

Let’s dive in:

Position: Starting pitcher
Age: 36 (Jan. 7, 1984)
Height: 6-foot-4
Weight: 240 pounds
Bats: Left
Throws: Left

2020 stats:
12 games (12 starts)
3-3 record, 5.16 ERA, 42 strikeouts
1.38 WHIP, 5.14 FIP, 6.2 K/9,

Career stats:
424 games (423 starts)
193-111 record, 3.60 ERA, 2,397 strikeouts
1.265 WHIP, 3.69 FIP, 8.3 K/9

Why Lester makes sense for Red Sox:
Listen, the Red Sox need a pitcher they can rely upon to take the ball every five days and deliver a somewhat quality outing. Lester should be able to do that. He made at least 30 starts every season from 2015 to 2019 and didn’t miss a turn in 2020.

Plus, he’s a proven big-game pitcher who isn’t fazed by pitching in Boston. That much always has been true.

Finally, let’s be honest: It would be cool to see Lester finish his career, and potentially pick up his 200th win (he’s at 193) in a Red Sox uniform. It’s not wrong to root for storybook endings.

Why Lester doesn’t make sense for Red Sox:
Does it make more sense for the Red Sox to sign an aging pitcher who, at this point, is below average-to-average and probably will post an ERA around 5.00 or to give a young player and/or a reclamation project a shot?

Lester has had a great career, but he has not been good in recent seasons. He very much deserved the 4.46 and 5.16 ERAs he posted in 2019 and 2020, respectively. Sure, he finished ninth in National League Cy Young Award voting in 2018, but the downward trend since then is impossible to ignore.

The fact of the matter is that Lester, who will turn 37 in January, just isn’t that good anymore. Is he still a big league-caliber pitcher? Absolutely, but the Red Sox can, and probably should, shoot higher.

Verdict: Not a fit.

Prediction: It pains us to say this, but… Lester to the New York Yankees on a one-year, $6 million contract. Chase that ring, Jon — you’ve earned it.

Thumbnail photo via Rick Osentoski/USA TODAY Sports Images
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