Jon Lester should have been a Red Sox for life

Podcast Episode
WEEI’s Live BP Show
Live BP, Ep. 4: Looking back at Jon Lester
Listen Now
Now Playing
Now Playing

Did you know that Jon Lester had an offer to play professional soccer in Europe? Did you realize he dunked a basketball in eighth grade? Oh, and something else ... Did you truly not know this is a player who should have not worn any other uniform but that of the Red Sox?

It's easy to wax poetically when a player retires, as Lester just did (via, looking at all the what-might-have-beens and what-should-have-happened. That's how it works, especially when you are talking about a pitcher who won 200 regular season games, played key roles in three World Series titles and saw 16 major league seasons.

But Lester's place in Red Sox history is so unique, the exercise is actually worthwhile. For a variety of reasons, we're talking about one of the most impactful pitchers in Boston baseball history.

The declaration is rooted in what Lester did on the field in a Red Sox uniform. As a 23-year-old cancer survivor, he closed out the 2007 World Series with a Game 4 win in Colorado. The following season he threw a no-hitter before propelling his postseason reputation with lock-down performances against the Angels and Rays.

From 2008-11, only three pitchers totaled more wins than Lester's 65, with the lefty combining for a 3.33 ERA during the four-year span.

Then came the 2013 postseason, a stretch that Lester entrenched himself in Red Sox lore for good. Five starts, four wins and a 1.56 ERA. Who knew that just a few months later so much good would turn into a historic wave of bad.

Heading into his contract season in 2014, the Red Sox offered Lester a four-year, $70 million deal. They might have well offered Tuukka Rask's Bud Light contract. What was telling was how this reality came to light, with the lefty's loyal teammates as upset as anyone that the team had taken this approach, leaking out the embarrassing figure.

The following offseason, Lester came on WEEI and admitted he would have signed on the dotted line if the Sox offered somewhere in the vicinity of six years, $120 million ... otherwise knowing as less than the going rate for a pitcher of his caliber.

Lester's side and the Red Sox never really communicated much after that. The distrust from the lefty's camp was too much to overcome.

Five years later, John Henry sat outside JetBlue Park and said, "I think we blew the Jon Lester negotiations." They did.

That was just the beginning of the pain inflicted by the Red Sox' botchery.

According to a source familiar with the negotiations, when it became evident that the Red Sox were going to deal Lester at the 2014 non-waiver trade deadline, the offers were all minor league prospects, with Baltimore's Dylan Bundy serving as the most intriguing. But for fear of giving the perception that they were taking a step back with a hint of rebuilding - (boy, how times have changed) - the Sox went with the only big leaguer offered, Yoenis Cespedes.

The conversation regarding the return for Lester is another story, with the Red Sox at least turning the mercurial Cespedes into Rick Porcello the following offseason. But what the deal did was show Lester there was life outside of Boston, even if it was the low-budget world of the Oakland A's.

Because of Lester's eye-opening regarding another organization, when the Cubs came in hard the southpaw's ears were wide open, especially when it came to the six-year deal offered by Theo Epstein. This led to another misstep by the Red Sox, who capped their interest in Lester instead of doing whatever it took to get back their former ace.

One offseason later, after learning the lesson that came with a rotation involving Justin Masterson/Joe Kelly/Clay Buchholz/Wade Miley/Rick Porcello, Henry and Co. reverted back to the time honored tradition of not being outbid, no matter what. It had worked for Carl Crawford, John Lackey, Pablo Sandoval and Hanley Ramirez. This time it was David Price.

The Red Sox had officially cost themselves at least $80 million in not valuing Lester as the ace they ended up chasing.

Make that $80 million and two of the game's best prospects (Michael Kopech, Yoan Moncada) after it was deemed that Price was more of a Lackey than a Lester, leading to the trade for Chris Sale.

It didn't stop there.

At the end of spring training, about a month after Henry tipped his hand by declaring that the Red Sox were going to learn their lesson from the Lester negotiations, the Sox signed up Sale to an extension despite not having seen him pitch following an injury-impacted 2018.

In late June 2019, Sale admitted to that he had every intention of re-signing with the Red Sox and not going to free agency. In other words, the Sox didn't correctly read the room. And while Sale may go on to be a staff leader once again, since signing the extension he is 11-12 with a 4.12 ERA in 34 starts.

Five years after the fact, the Red Sox were still chasing their tails because of the Lester misstep.

When Lester showed interest in returning to the Red Sox prior to 2021 the team's decision-makers showed no interest, leaving the lefty with a one-year deal in Washington, that ultimately included a stint with the Cardinals. He didn't have a great year, but it wasn't any worse than a pitcher they prioritized over Lester, Martin Perez.

The story of Lester should be rooted in a flurry of on-the-field moments, along with the kind of impact he had on so many of his teammates while living the life of a Red Sox. But the other piece of the puzzle - the path to Lester putting the Sox in the rearview - should be part of the conversation.

For one final time we will scream it from the mountaintops: Jon Lester should have been a Red Sox for life.

Featured Image Photo Credit: USA Today Sports