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Jon Lester’s Career: A Look Back

After 16 big league seasons and 3 championships, long-time Red Sox and Cub Jon Lester has called it a career.

Image: @RedSox/Twitter

On Wednesday morning, news broke that left-handed pitcher Jon Lester was retiring from baseball. Lester, now 38 years old, played 16 seasons in the big leagues with Boston, Oakland, Chicago, Washington, and St. Louis. In that time, he racked up 5 all-star appearances, 200 wins, 3 World Series rings, an NLCS MVP, as well as owning a 2.51 ERA across 154 postseason innings.

Anytime a player of Lester’s caliber retires, it’s natural for the conversation to immediately turn to the player’s chances of being enshrined with a plaque in Cooperstown. While these conversations can be fruitful and become necessary once the player finally hits the ballot, it’s important to simply celebrate the accomplishments of the player for what they are, rather than rushing to compare them to other greats. Ultimately, barring a major swing in the electorate, Lester will likely fall short of enshrinement, but that doesn’t take away from his great career. Today, we’ll be taking a look back at some of the high points of that career.

Lester began his career in June of 2006 with the Red Sox. At age 22, Lester was the youngest player on the roster that season. While he struggled in his debut (3 runs in 4.1 innings), he rebounded quickly, posting a 2.95 ERA across 21.1 innings in that first month of action. Lester’s rookie season came to a premature end, as he landed on the injured list with back pains in late August. After several meetings with doctors at Massachusetts General Hospital, Lester was diagnosed with Lymphoma. After undergoing chemotherapy that offseason, Lester would get a late start to his 2007 season.

After several rehab appearances, Lester returned to the big leagues on July 23rd in Cleveland. Simply returning to professional athletics at all after such a diagnosis and treatment was heroic, his performance - that day and the rest of his career - was all gravy. Lester led the Red Sox to victory that day, striking out six Guardians across six innings while allowing just two runs. Through the end of the regular season, Lester would make 10 more starts (as well as the lone regular-season relief appearance of his big league career), and while his run prevention in 2007 was about league average (104 ERA+), his story and year were far from average.

The 2007 Red Sox went 96-66 en route to an AL East division championship. After sweeping the Angels in the Division Series and knocking out Cleveland in seven games, Boston found themselves in the World Series again, just three years after breaking the curse. The Red Sox quickly jumped out to a 3-0 lead in the series and handed the ball to Jon Lester in a potential Championship clinching game 4. Lester delivered in spades, allowing zero runs on just three hits while pitching into the sixth. While the men behind Lester faltered a bit, allowing the Rockies to pull within a run, closer Jonathan Papelbon was able to slam the door shut in the 9th, clinching Boston’s second World Series championship since the turn of the century, and none other than Jon Lester was the winning pitcher in the clinching game.

Already a World Champion, Lester accomplished one of the most impressive feats for an individual the following year. On May 19th, the Red Sox welcomed the Kansas City Royals to Fenway. Jon Lester got the start opposite Luke Hochevar. Lester made quick work of the top of the Royals’ order in the first, recording his first strikeout of the day against Mark Grudzielanek. In the second, Billy Butler worked a one-out walk. With a 1-2 count two batters later, Lester attempted a pickoff. Throughout his career, Lester earned a reputation as being unable to throw to first base. While a relatively common mental block for pitchers, Lester would become the poster boy for it. This attempt was no different, as an errant throw allowed Miguel Olivo (who reached on a fielder’s choice) to advance to second base. He would be the only Royal to make it that far on this day.

From there, Lester cruised until the ninth, not allowing a baserunner and striking out seven more. Just like that, the 24-year-old was 3 outs away from baseball immortality. The leadoff hitter walked. The next two batters grounded out. The final batter, Alberto Callaspo, stepped into the box. On a 1-2 count, Lester got Callaspo to punch out swinging. Jon Lester had no-hit the Kansas City Royals.

We fast forward now to Lester’s second ring, 2013. Now the ace of the staff, Lester was a crucial part of that championship run, delivering time and time again. In Game 1 of the division series, he held the Rays to just 2 runs on 3 hits over 7.2 innings. In Game 1 of the ALCS, he was a tough-luck loser, as he allowed just one run, but the Red Sox would go on to lose 1-0. He would pitch in another one-run game in Game 5, this time emerging as the victor in a 4-3 Boston win. In the World Series, Lester elevated his game one notch further. In two starts, he tossed 15.1 innings, allowing just a single run while striking out 15. For his efforts, Lester received his second ring. Had it not been for the historic performance of David Ortiz in that year’s fall classic, he likely would have taken home a World Series MVP award as well.

Jon’s next bout of postseason greatness came in 2016, now with the Chicago Cubs. Once again, Jon wasted no time, delivering a fantastic start of 8 innings of shutout baseball in Game 1 of the division series against the Giants. He kept rolling into the NLCS, where he again started games 1 and 5. Once again, he was fantastic, allowing just one run in each outing, going 6 and 7 innings respectively. This was enough to earn him series MVP honors, a distinction he shared with teammate Javier Báez. Later that postseason, Lester got the opportunity to pitch in what might be the greatest game ever.

The 2016 World Series featured the Guardians and the Cubs, who had not won a championship since 1954 and 1908 respectively. Either way, a generationally long drought would come to an end. When Kyle Hendricks issued a walk to Cleveland’s Carlos Santana with two down and nobody on in the fifth, Cubs manager Joe Maddon got the hook out, opting for his veteran lefty Jon Lester to face the left-handed-hitting Jason Kipnis. While the move didn’t pan out immediately, as Lester allowed both the inherited runner and Jason Kipnis to score on a wild pitch, Lester managed to settle in, providing the Cubs with much-needed length, as he went 3 innings while allowing just one earned run. The Cubs would go on to win the game in the tenth inning, securing Jon Lester the third ring of his career.

Lester might be a Hall of Famer, he might not be. Frankly, I do not care. He had a fantastic career that most players can only dream of. He tossed a no-hitter, won championships, made all-star games, broke a 108-year curse, and beat cancer. He will no doubt be enshrined in the Red Sox Hall of Fame, and will forever hold a place in my heart as the first true ace I can recall watching.


Matt O’Halloran is a junior mathematics major at the University of Massachusetts Lowell. He works in analytics with the school’s baseball program. He is a writer for Beyond the Box Score and an editor at Diamond Digest. He can be found on Twitter @matto20.