February 29, 2024

Fort Myers, Florida: On Thursday, Jon Lester assisted as an instructor at the Red Sox spring training camp. Arriving for a few days, the 40-year-old retired pitcher last threw for Boston on July 25, 2014, which was almost ten years ago.

 

It’s a little strange. When asked what it was like to come back and don a Red Sox hoodie once more, Lester replied, “I won’t lie.” It’s different just to be on this side of it. gaining some understanding of how the staff and coaches get ready for the day.

 

That aspect of the game was never shown to me. So, cool but a little strange. Being with the men is enjoyable; notice how things have streamlined here. Everything has changed significantly from a few short years ago. It’s quite awesome.

 

Lester was a key player in Boston’s two World Series victories in 2007 and 2013. However, on July 31, 2014, two months before he was eligible for free agency, the Red Sox dealt him to the Athletics.

 

Lester desired to rejoin the Red Sox as a signatory. However, during spring training 2014, Boston lowballed him with an offer of a four-year, $70 million contract extension. In December 2014, Lester signed a $155 million, six-year contract with the Cubs during his free agency.

 

Lester remarked, “Anytime you get to be a part of this organization, it’s pretty cool.” “Since leaving in ’14, I’ve clearly developed and grown up. With that, you realize that there are moments when the business aspect of this game is lacking. It’s also challenging when you’re in the heat of the moment.

 

It can be challenging to comprehend why certain things occur and what may have been going through their minds. However, the more you distance yourself from the circumstance, the more you develop into an adult and learn that, despite the game’s beauty, business occasionally comes in the way.

 

I suppose I was a byproduct of that. However, it’s quite unique to be returning and to have been invited here. It goes without saying that this organization’s history, as well as my own, are fairly awesome.

 

Red Sox owner John Henry said during spring training 2019 that the team mishandled the Lester negotiations.

 

On February 18, 2019, Henry stated, “I believe the Jon Lester (negotiations) was a bust.” “We made a huge mistake by re-signing him during spring training. Therefore, for reasons that are now very obvious—I won’t go into them here— but they are now plain.

 

Lester expressed his excitement at receiving an invitation to visit from Chief Baseball Officer Craig Breslow.

 

“I believe that even after you stop playing, you still want to be a part of something,” Lester, who announced his retirement prior to the 2022 campaign, stated.

 

Lester isn’t shocked to learn that manager Alex Cora and Breslow, two former colleagues, are in charge of the Red Sox.

 

Lester remarked, “I think it just makes you feel older than anything.” It’s awesome. I believe we all kind of understood that he was going to do this one day and be successful at it, including me when I first came to the Red Sox with AC here.

 

He has undoubtedly shown that. And given Brez’s history and pedigree, it’s evident now that I kind of assumed that’s where he was going to wind up too. Thus, it’s kind of cool that we’re all here. Brez is clearly incredibly smart and skilled, so I’m sure things will get better here pretty soon with him up there.

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