Red Sox must remove emotion from the Jon Lester equation this winter

CHICAGO, ILLINOIS - SEPTEMBER 26: Jon Lester #34 of the Chicago Cubs during the game against the Chicago White Sox at Guaranteed Rate Field on September 26, 2020 in Chicago, Illinois. (Photo by Quinn Harris/Getty Images)
CHICAGO, ILLINOIS - SEPTEMBER 26: Jon Lester #34 of the Chicago Cubs during the game against the Chicago White Sox at Guaranteed Rate Field on September 26, 2020 in Chicago, Illinois. (Photo by Quinn Harris/Getty Images) /

The Red Sox have a chance to bring Jon Lester home this winter

Free agency is here my friends and so far it’s been silent on the signing front. For the Red Sox, this winter will be about building upon the foundation that they have and repairing some holes along the way. The pitching staff will surely be the belle of the ball for Chaim Bloom and there isn’t a shortage of arms on the market. One that will for sure catch Boston’s eye is Jon Lester, and they need to be careful if they approach the southpaw.

When I say they need to be careful it isn’t because of any character issues or even injury woes. Hell, Lester has only missed 33 days of action on the IL since 2017, that’s pretty damn good, especially when you look at Boston’s IL numbers for pitchers. Obviously, he’s on the wrong side of 30 as he’ll be turning 37 just after the New Year. He’s still incredibly effective on the mound and is just two seasons removed from winning 18 games back in 2018.

I bring of Lester for a reason here, despite other names getting the shine this offseason, we know of his connection to the Red Sox. We also know that Boston’s ownership group have regretted how they treated the lefty when he made his exit from the organization back in 2014. Tom Werner has been very open with his feeling on the matter and how he wishes they would’ve handled the situation differently to keep Lester in Boston for his entire career.

Well, they have a chance at a re-do this winter and I wouldn’t be surprised to see their names in the talks to sign the free-agent starter. His most recent deal in Chicago, a 6 yr/$155M whopper has finally come due and the Cubs are willing to let him walk. Or they’re at least willing to let him dip his toes in the water to see what’s out there and could possibly re-sign him for a club-friendly salary.

After the debacle that was the 2020 Red Sox, they need to tread very lightly here, especially with the budget. Per Christopher Smith of, the Red Sox are more than $40M under the CBT and are sitting pretty to shop this winter. However, they can’t go on a spending spree just to get themselves back into the trouble that they were heading into this past season. With how much FSG cared and still cares for Lester, they may be blinded by that affection, which will not end well for their wallets.

I feel that signing Lester and bringing him back to Boston to finish out his career is that storybook ending we all strive for, especially in sports. Long gone are the days where a player spends his entire career with a single team. Obviously, there are still some cases but loyalty isn’t just what it used to be in the sports world. So I’m all for bringing him back, but the deal has to be right, and Bloom isn’t one to spend foolishly.

I’m not expecting something longterm for Lester and the Sox here but I could see something in the way of three years, to get him to his 40th birthday. So if Bloom were to call up the southpaw and offer him a contract in the ballpark of 3 yrs/ 36M, I could see that being in his wheelhouse.

It won’t break the bank for Boston and it’s a realistic wage for a guy pushing 40 that will likely be at the bottom of the rotation. It’s well under what Lester was earning in Chicago, but he also signed that deal quite a while ago and can’t be harped on too heavily.

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Again, I worry that Chaim would want to offer Lester a hometown discount, but Werner or someone else in the FSG offices would pressure him to increase the offer to make-up for their mishandlings the first time around. They need to let Chaim do what he does best and remove all emotions from the equation if they negotiate with Lester.

Let’s not forget, Jon has also made statements that he’d like to come back to Boston to finish his career. So the fish is already on the hook, there’s no need to load on more bait to reel him in. As for Red Sox Nation, I think that Lester would be welcomed back with open arms. When he was traded in 2014 it wasn’t due to anything he did.

For some reason, Boston thought that trading him to Oakland then lowballing him in the off-season was going to work. Now that his playing years are winding down, a sweetheart deal to finish his career where it began is definitely in play. Again, this is just wishful thinking from a Lester guy, but with both sides pining about their time together, it feels like the relationship very well could be reignited.

Next. Just do it, get DJ Lemahieu. dark

Adding Jon Lester to the Red Sox bullpen could very well be a win-win for both sides. Not only would they be adding a reliable veteran arm that is rarely injured but he’d get to end his career where it all started. Just thinking about him taking the mound at Fenway Park again, hopefully in front of fans, gives me chills. It can be done but it needs to be done for the right price and right terms for all involved. I think deep down bringing him back to Boston is on the docket for FSG, they just need to be smart about how they go about it and keep their emotions close to the vest.