Jon Lester’s retirement reminds us Red Sox never should have let him go

Jon Lester should have been a Boston Red Sox for life

Jon Lester is retiring after a 16-year career, more than half of which was spent with the Boston Red Sox, according to ESPN’s Jesse Rogers.

The announcement closes the book on a remarkable career. 200 wins, five All-Star appearances, three World Series titles. Those accolades only begin to sum up Lester’s contributions on the mound.

Lester’s retirement brings a wave of fond memories washing over Red Sox Nation. The lefty came up through the Red Sox farm system and he made his major league debut with the club in 2006. After being diagnosed with non-Hodgkin lymphoma later that year, Lester returned as a cancer survivor the following season and closed out the 2007 World Series with a Game 4 win in Colorado. He tossed a no-hitter in May 2008 against the Kansas City Royals, which still stands as the most recent no-hitter in Red Sox history. He won 19 games while leading the league with a 9.7 K/9 to finish fourth in the Cy Young race in 2010.

We can’t discuss Lester without bringing up his postseason heroics. Tossing nearly six shutout innings in the decisive game of the 2007 World Series was a great story but his performance in the 2013 postseason was legendary. Lester earned four wins in five postseason starts while posting a stellar 1.56 ERA to lead the Red Sox to another championship.

Lester earned the admiration of the fanbase as he emerged as the ace of the Red Sox staff. He seemed poised to lead this rotation for years to come, only for his tenure to come crashing to a bitter end as the result of the misguided meddling of Red Sox ownership.

Heading into his contract season in 2014, Lester let it slip that he was open to a team-friendly deal to remain in Boston. He loved this city and wanted to remain loyal to the only organization he had ever known. John Henry and his cronies in the Red Sox ownership group took that admission as an opportunity to throw a lowball offer in Lester’s direction, presenting him with a four-year, $70 million extension.

They had to know that ridiculous offer wasn’t going to be enticing enough to keep Lester from testing free agency. Henry viewed it as a starting point in negotiations, assuming a counter-offer from Lester would lead to some back-and-forth that eventually would land on an agreeable contract. Unfortunately, the Red Sox misjudged their starting point with an offer so low that it felt like a slap in the face to their ace. The offer was met with silence from Lester’s camp and negotiations never moved forward after that.

With the Red Sox spiraling as the 2014 trade deadline approached, Lester was dealt to the Oakland A’s for Yoenis Cespedes in a desperate attempt to salvage some value from their ace before he hit free agency.

His stay in Oakland was short-lived but the experience opened Lester’s eyes to the possibility of pitching for another franchise. The window to lure him back on a team-friendly deal had slammed shut. Boston made an effort to re-sign Lester that winter but they weren’t willing to compete with the six-year, $155 million offer from the Chicago Cubs.

The $25.8 million average annual value made Lester the second-highest-paid pitcher at the time behind Clayton Kershaw. The Los Angeles Dodgers ace had won the NL Cy Young award in three of the previous four seasons while Lester had never finished higher than fourth for the AL award.

The Cubs aggressively overbid the market for Lester and it paid off. Even if Lester’s track record didn’t warrant a salary in the elite tier, nobody in Chicago will ever complain after he helped deliver the Cubs their first World Series title in over a century.

It’s a bit more understandable why the Red Sox weren’t willing to pay that much. What stings is that they let him go with the knowledge that it wouldn’t have taken that much to keep him. Lester admitted during an appearance on WEEI that an offer in the vicinity of $120 million over six years would have convinced him to sign an extension with the Red Sox. They never approached that territory until it was too late.

The $20 million average annual value on a $120 million contract isn’t all that far off from the $17.5 million the Red Sox had already offered. It shouldn’t have taken much to close the gap through negotiations. The problem was that the total dollars were well short since the Red Sox were reluctant to go beyond four years while Lester wanted six.

In retrospect, the Red Sox should have swallowed hard and given in to the six-year demand. When you bid on expensive star talent in free agency, you have to assume there will be some decline on the backend of the deal. You’re paying for the peak years early in the contract while crossing your fingers that the player doesn’t turn into a bust too soon. A down year or two at the end of a long contract is common for these deals. Boston tried to avert that scenario by sticking to four years, a period in which they expected Lester to remain effective.

As it turns out, they weren’t entirely wrong. Lester was an All-Star in two of his first four years in Chicago. He was the runner-up for the NL Cy Young in 2016 and the NLCS MVP on the way to winning the World Series that year. Winning 18 games earned him a ninth-place finish on the Cy Young ballot in 2018, which would be his last strong season.

Lester posted a mediocre 4.46 ERA while allowing a league-leading 205 hits in 2019. His production fell off a cliff during the shortened 2020 season when he posted a career-worst 5.16 ERA and saw his strikeout rate decline sharply to 6.2 K/9.

He was still a solid rotation option in 2019 but not the ace he was being paid to be. That production wouldn’t have seemed terrible if the Red Sox had him signed for $20 million that season, the price that middle of the rotation pitchers are now getting paid. His 2020 season was brutal but did you see the arms that the Red Sox were trotting out to the mound that year? Lester could have been one of their top starters that season even at that advanced stage of his career.

One of the most telling arguments in favor of why Lester was worth keeping despite concerns about the backend of the deal is his nearly identical production in Boston and Chicago.

Lester with the Red Sox (nine seasons): 3.64 ERA, .631 winning percentage
Lester with the Cubs (six seasons): 3.64 ERA, .631 winning percentage

Yes, a six-year deal would have turned ugly by the end of it but he earned his salary for the majority of the deal. The team-friendly offer he supposedly would have accepted while he was still with the Red Sox would have been a tremendous bargain for the first four years and the discount would have mitigated the downside of paying for a down year or two at the end.

Henry eventually admitted that he botched the Lester negotiations. The Red Sox overcompensated in their attempt to rectify the mistake, shelling out a massive $217 million deal for David Price. Boston got four somewhat underwhelming (somewhat turbulent) seasons out of Price before shedding half of his remaining contract in a salary dump deal with the Dodgers. The Red Sox would have gotten more out of Lester at a cheaper salary.

There may have been a tinge of regret regarding the backend of the deal if the Red Sox had outbid the Cubs in free agency to bring Lester home. Topping that offer would have seemed borderline reckless based on the market at the time. It wouldn’t seem quite so bad by the time we reached those decline years though considering how high the price for an ace pitcher has risen since then. It would have felt like the Red Sox dodged a bullet if keeping Lester meant passing on Price. The benefit of hindsight makes it easier to see that letting him go to Chicago was a mistake.

We don’t need hindsight to know that lowballing Lester with a disrespectful offer was a foolish decision. We knew that as it was happening. Boston should have been able to extend Lester with a very reasonable $120 million deal in 2014 but they got greedy. By ownership trying to play hardball, Lester ultimately took his ball and left to throw it for another team.

While fans will always wish that Lester had spent his entire career in Boston, we still have plenty of great memories from his days spent in a Red Sox uniform. As we celebrate his career following news of his retirement, we should cherish the highlights from the time he was here rather than dwell on the bitter way that he left.