Former Red Sox hurler Jon Lester made headlines when he announced his retirement after a 16-year career. Throughout his career, Lester won three World Series titles (two with the Boston Red Sox), amassed 200 wins, and made five All-Star teams. 2021 wasn’t the best swan song, as a 5.29 ERA isn’t the ideal way to go out, but besides that Lester put up some great numbers during his career.
Lester had big-time moments during his career. One of them is his 2008 no-hitter against the Kansas City Royals where he threw 130 pitches. There was also his return to baseball in 2007 after a battle with lymphoma. In his first start that year, he and the Red Sox defeated the Cleveland Indians. Lester pitched six innings, allowed just two runs, and struck out six. On top of that, he was a key member of the Chicago Cubs‘ World Series run in 2016. Jon Lester has definitely had his moments.
Not many pitchers make five All-Star teams and finish top five in Cy Young voting three times (runner-up in 2016). Lester is one of those pitchers. So with that said, is it out of the realm of possibility that we could see Lester in Cooperstown in the future?
For this, we are going to dive into the two best stretches over Lester’s career. The first stretch we’re going to dive into are the 2008-10 seasons. This is a three-year stretch with the Red Sox where we saw him accumulate a 14.6 WAR (according to Fangraphs) and establish himself as one of the game’s top-end starters.
To add more context, let’s see what that 14.6 WAR did for him. That WAR was good for tenth in MLB over that three-season stretch. Lester is sandwiched in between former greats such as Dan Haren (ninth) and Jered Weaver (11th). Lester is also tenth in ERA, ninth in FIP, and 16th in innings pitched. For the aforementioned Haren and Weaver, they aren’t quite Cooperstown caliber, but they were among some of the better known (and performing) pitchers of that time.
Speaking of that time, some of the kings of the mountain were the likes of Roy Halladay ( 19.7 WAR), CC Sabathia (18.7), and Felix Hernandez (17.1). Halladay is already in the hall while Sabathia and Hernandez will find themselves enshrined at some point as well. Lester wasn’t quite as dominant as those guys, but when you look at top ten categories for this time, you will more than likely see Lester’s name around those other guys.
The second prime stretch are his years from 2014 to 2016. This last prime stretch was mostly spent outside of the friendly confines of Fenway Park as Lester was traded in during the 2014 season to the Oakland Athletics. He would go on to Chicago where he’d go on to win his third and final World Series ring.
During this period of time, Lester’s WAR was quite comparable to his 08-10 WAR. His 14.5 WAR for 14–16 was 14.5, that’s good for 7th during this stretch. This time he’s in the Jake Arrieta (sixth) and Jose Quintana (eighth) range. Again, future Hall of Famers such as Clayton Kershaw, Max Scherzer, and Corey Kluber dominated this time period.
As far as accolades for Lester during his best stretches, he was never able to win the Cy Young award although he finished top ten four times (2010, 2014, 2016, 2018). At this time there was no All-MLB team to be selected to, so the best of Lester’s individual accolades are his five all-star selections and his 2016 NLCS MVP with the Cubs.
During these stretches, it should also be stated that Lester was the ace of these staffs. That definitely should be considered when evaluating someone’s Hall of Fame candidacy. An ace carries the burden of being the team’s most consistent, and reliable pitcher. When the team is on a losing streak, the ace is expected to stop it. During high leverage playoff moments, he is tasked with anchoring the ship and leading the way.
So what does this current Hall of Fame, and former World Series MVP have to do with Jon Lester? Well, Jack Morris never received the required 75% of the vote during his eligible years from 2000 to 2014. Morris was enshrined after he was elected by the Veterans Committee in 2017. Could this be Lester’s path into the hall? Morris was the guy for his Minnesota Twins team that took home the 1991 title.
Let’s compare Lester with Morris. Morris has an excess of 450 career starts (527) and an above 43 career WAR (43.61). Lester, meanwhile, has a higher career WAR at 46.2. Not only that, Lester bests Morris in career ERA, ERA+, WHIP, and FIP. Lester, just like Morris was the first or second starter for most of his teams throughout their respective careers. Lester was an integral part of three championship teams, while Morris was for three as well.
This particular comparison makes Lester’s hall chances a little more feasible. Besides Morris, Lester has a higher career WAR than notable hall members like Catfish Hunter, Burleigh Grimes, and Jim Kaat. With that being said let’s look at the opposing side that would keep Lester outside of Cooperstown.
The Case Against
As stated earlier, the lack of individual accolades could be what hinders Lester’s case the most. Again in 16 seasons, he only finished top 10 in Cy Young voting four times, with his highest finish being runner-up in 2016. Yes he has that NLCS MVP, but that is below what someone that was on the fringe like the aforementioned Jack Morris accumulated. Morris finished top ten in the Cy Young seven times in 18 years and even garnered some MVP votes in five different seasons.
Detractors may point to the fact that Lester was indeed very good, but he wasn’t great. While he was arguably the best starter for his three championship teams, he was never considered the very best of his era. Like we pointed out earlier, in his two greatest stretches (08-10 and 14-16) he was still under the likes of Cliff Lee, Sabathia, Scherzer, and Kershaw.
Take another player like Andy Pettitte. Pettitte has a much higher career WAR (60.7) than Lester, won more championships (5-3), more top ten Cy Young finishes, and more years garnering MVP votes was only up to 13.7 % of the required votes to be enshrined in his third year on the ballot in 2021.
|Avg HOF Pitcher||4||66.0||237||163||.591||3.01||587||426||233||37||3532||3255||1473||2042|
Jon Lester, Dan Haren, Jered Weaver, Roy Halladay, CC Sabathia, Felix Hernandez, Jake Arrieta, Jose Quintana, Clayton Kershaw, Max Scherzer, Corey Kluber, Jack Morris, Catfish Hunter, Burleigh Grimes, Jim Kaat, Cliff Lee, Andy Pettitte