It appears 2021 was the last chapter in the story book that is Jon Lester’s playing career. The 38-year-old announced his retirement by way of an article with ESPN’s Jesse Rogers, stating that after a 16-year career “his body just isn’t up for the rigors of a major league season anymore.”
So what is the legacy of Jon Lester? Where is a place in history for a five-time All-Star, three-time World Series winner, and National League Championship Series Most Valuable Player?
Jon Lester broke into Major League Baseball back in 2006 with the Boston Red Sox, registering his first start on June 10 against the Texas Rangers. He would go on to have a middling rookie season, producing an exactly league average adjusted earned run average of 100 over the course of 15 starts.
It was discovered during his rookie season that Lester had anaplastic large cell lymphoma, a treatable form of cancer. He received treatment in the offseason and was declared cancer free in December of 2006.
Due to the treatment, Lester would not return to the Red Sox until midway through the following season, limiting him to a total of 63.0 innings pitched. He added his first piece of hardware to his collection in 2007, being voted the Tony Conigliaro Award winner, given to the player who best overcomes an obstacle of adversity through the attributes of spirit, determination, and courage.
Along with that, Lester would add a World Series ring, his first of three. Lester made three appearances in the 2007 playoffs, coming out of the bullpen twice and starting one game. The one game Lester started happened to be game four of the World Series against the Colorado Rockies. He went five and two thirds innings, allowing three hits and three walks while striking out three and not allowing any runs. This would set a theme for the career of Lester, as he would prove time and time again to be a dominant force in the postseason.
Red Sox Prime
Beginning in 2008, Jon Lester established himself as a franchise icon in Boston. Over the span of 2008 to midway through the 2014 season, Lester was electric every time he touched the mound. He produced an ERA+ equal to or greater than 110 in every single season apart from 2012. Not only was he effective, but the Washington native was also always towards the top of the leaderboard in innings pitched, cracking the 190 innings pitched mark in every single season from 2008 onward.
When it came to awards, Lester began to rack them up. Three All-Star appearances and two fourth-place finishes in Cy Young voting established Lester as one of the most dominant, and most feared pitchers in the American League in the early 2010’s. During this time Lester also pitched the single best game of his career, a no-hitter in 2008 against the Kansas City Royals in which he walked two and committed one throwing error but struck out nine.
His postseason dominance continued in 2013. En route to a second World Series ring with Boston, Lester made five starts in the postseason and went 4-1 with a 1.56 ERA over 34.2 IP. He was most dominant on the highest stage, making two starts in the World Series and only allowing a single earned run over 15.1 IP.
Over the course of his time in Boston Lester would rack up 110 wins to 63 losses, a 3.63 ERA, 120 ERA+, and 1,386 strikeouts of which he accumulated over 1,519.1 IP.
Brief Stint in Oakland
In 2014, on the last day of July, Lester would be moved to a new team for the first time. With his contract coming to an end at the conclusion of the 2014 season, the Red Sox traded a half-season of Lester, as well as Jonny Gomes for Yoenis Cespedes and a 2015 competitive round draft pick.
Lester settled in nicely with his new club, making 11 starts and pitching very well in all of them. He would go 6-4 in that half year, compiling an ERA of 2.35, with 71 strikeouts and an ERA+ of 159 over 76.2 IP.
Lester started the Wild Card game for the A’s, facing off against the upstart 2014 Royals. While Lester allowed four runs to score, the A’s had a substantial 7-4 lead with one out in the eighth, but Lester could only watch from the benches as that lead would crumble, and his brief stint as an Athletic would end.
Lester Goes to Chicago
Coming off the heels of a fourth-place finish in Cy Young voting, Lester was a hot commodity the first time he hit free agency. The Chicago Cubs set their sights on Lester, timing their $155 million injection of cash in coordination with the rise of their uber-talented farm system. Spoiler alert: it worked just as well as the Cubs could have hoped.
Lester was an above average pitcher his first year in Chicago, but nothing all that spectacular in the regular season. Peripheral stats like FIP indicated that Lester should have performed better than actual results showed, however the Cubs would make the playoffs all the same. The 2015 postseason was not one of the finer moments of Lester"s career either, going 0-2 with a 4.50 ERA.
The next year, the Jon Lester that Chicago had relied on becoming a franchise cornerstone, showed up in full force. In 32 starts, Lester went 19-5 with a league-leading .792 winning percentage. He tossed over 200 innings with a 2.44 ERA, second best in MLB behind his teammate Kyle Hendricks. Hendricks, Lester, and Jake Arrieta would form a nasty triumvirate that would guide the Cubs to a 103-win season.
If you are at all a baseball fan, you know the story of the Cubs 2016 postseason, arguably one of the best stories in the history of sport. Lester was a massive part in that. He made six total appearances for the Cubs in the postseason, five of them starts. He proved to be a key piece during the NLCS against the star-studded Los Angeles Dodgers, winning a co-MVP award along with teammate Javier Baez for his herculean efforts on the mound. In the NLCS he made two starts, pitching a total of 13 innings to the tune of a 1.38 ERA. He played so well that Lester himself added 11.1 percent cWPA, meaning the Cubs were 11 percent more likely to win the World Series because of his efforts than they would have been without him. (In his second World Series with the Red Sox Lester added 24.1% cWPA)
In the World Series against Cleveland Lester proved once more to be effective. He took the loss in game one, getting roughed up but still putting together an average start, allowing three runs. Regardless of whether he allowed one run or three, it would have been too many as the Cubs failed to send even a single person across home plate.
Lester’s second appearance in the World Series came in game five, an elimination game with the Cubs down in the series 3-1, playing for their lives in the confines of Wrigley Field. Lester did more than enough to earn the win and in turn keep the Cubs alive, allowing only two runs over six innings pitched. While he would not be available for any more starts for the remainder of the World Series, Lester did have a little bit left in the tank. Coming out of the bullpen in the fifth, Lester managed to produce three more innings of effective pitching, leaving him with a total of 14.2 innings pitched in the World Series. He only allowed one run before exiting, setting the stage for one of the best moments in the 21st century of baseball to follow.
When it comes to the remainder of his Cubs career, it was a mixed bag. Lester would earn what is now his final All-Star Game appearance in 2018, and at the conclusion of the year would end up at the top of the leaderboard in wins, good enough to receive a ninth-place finish in Cy Young voting. From there, it was rather evident Lester had passed his peak and was entering the latter stages of his illustrious career. He would stay with the Cubs through the shortened 2020 season before departing in free agency, signaling that the end was near for the core that led the Cubs to their first World Series title in a century.
Coming off the worst singular season of his career, Lester only found suitors in the form of short-term deals because of his age. He settled in Washington, joining the Nationals for a one-year $5M fee. No longer an above average pitcher, Lester played in our nation"s capital for just half a season before being shipped off to the Cardinals to help with their playoff push. While it was tough for Cubs fans to see Lester in the Cardinal red, they would not have to deal with it for long as he only made 12 starts in St. Louis.
Jon Lester, Hall of Famer?
The argument for Lester’s case of induction to Cooperstown is an interesting one to follow in the coming years. He is a 200-game winner, a postseason legend, five-time All-Star, and three-time World Series winner. His resume is chock-full of achievements, but is that enough to push him through?
If you compare Lester to the average Hall of Fame pitcher, it is evident he comes up short in a few key categories. The average pitcher in the Hall produced 66 career WAR, while Lester sits at 44.2 bWAR. When it comes to JAWS rankings, Lester is even further behind the pack. While the average Hall of Fame starting pitcher has a JAWS of 61.4. Lester has little to no black ink to speak of (in reference to leading a league in a key statistical category) ranking below pitchers like Miles Mikolas and R.A. Dickey for career numbers. Grey ink (top 10 in your league) is a little bit of a different story, as Lester does rank towards the top of the active players list, alongside future Hall of Fame company like Justin Verlander and Clayton Kershaw.
Do Metrics Tell The Whole Story?
On all accounts from purely a statistical basis, Jon Lester is not a Hall of Famer. On every comparative statistic Lester ranks below the average Hall of Fame starting pitcher, but do metrics tell the full story in this instance?
Lester dominated in the least quantifiable portion of baseball, the postseason. You cannot measure across eras, nor discriminate amongst those players that were unfortunate enough to play on teams not good enough to reach the postseason consistently, but you must find a way to give props to players who can get it done on the biggest stage.
Throughout his career Lester made 26 postseason appearances, pitching on the biggest stage three separate times, and nearly always getting it done. A career postseason ERA of 2.51 is proof of his dominance in fall, and the fact that Jon Lester is without a doubt one of the most dominant playoff pitchers so far in the 21st century.
Players have snuck in before under the bar of talent that had been previously established. Look no further than Jack Morris, the Hall of Fame pitcher remembered mostly for his time as a Detroit Tiger in the 1980s’. Jack Morris was a career 105 ERA+ pitcher, and Lester comes in with a career mark of 117. There is precedent for players of Lester"s caliber to find a place enshrined in the hallowed halls of Cooperstown, but it does not mean it would come without controversy regarding his career statistics.
If I were to bet on it, I would rely on Lester making the Hall of Fame. By no means is he going to end up a first, or second, or even third ballot Hall of Famer, but mark my words, he will be there. Lester is a textbook example of a tenth ballot type of guy. His career numbers are not staggering, but he has displayed enough talent, and been a significant part of enough major moments in the 21st century of Major League Baseball to earn a spot. Jon Lester, Hall of Fame class of 2037.
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