After a 16-year major league career, Jon Lester tells Jesse Rogers of ESPN he’s made the decision to retire. “It’s kind of run its course,” the 38-year-old said of his career. “It’s getting harder for me physically. The little things that come up throughout the year turned into bigger things that hinder your performance. I’d like to think I’m a halfway decent self-evaluator. I don’t want someone else telling me I can’t do this anymore. I want to be able to hand my jersey over and say, ’thank you, it’s been fun.’ That’s probably the biggest deciding factor.”
A second-round pick of the Red Sox out of a Washington high school in 2002, Lester entered pro ball as one of the more promising pitching prospects in the Boston system. Within a few years, the left-hander was ranked among the top farmhands in baseball and he made his big league debut at age 22 in June 2006. Lester was faced with incredible adversity just a few months into that run. He was diagnosed with anaplastic large cell lymphoma late in his rookie season, cutting that year short and requiring chemotherapy treatments.
Lester beat the disease and made an inspiring return to the mound in 2007. He made 12 regular season appearances that year, then pitched in three playoff games during the Red Sox’s run to a championship. Making his first career postseason start in Game 4 of the World Series against the Rockies, Lester tossed 5 2/3 innings of scoreless ball. He wound up getting the win in what proved to be the title-clinching game, as the Sox wrapped up a sweep.
Entering 2008, Lester was cemented as a key rotation member on Terry Francona’s staff. Incredibly durable, he’d make at least 31 starts over each of his next six seasons in Boston. While Lester only had two seasons (2009-10) with excellent strikeout numbers, he consistently demonstrated strong control and proved one of the game’s hardest pitchers to square up. A pillar of high-end consistency, Lester posted an ERA between 3.21 and 3.75 in five of six years from 2008-13.
Lester’s run in Boston was littered with accomplishments. He tossed a no-hitter in May 2008, earned back-to-back All-Star selections in 2010-11 and finished fourth in AL Cy Young award balloting during a 2010 season in which he tossed 208 innings of 3.25 ERA ball. Perhaps of most importance, Lester was excellent during the Red Sox’s surprising run to another championship in 2013. He pitched to a 1.55 ERA over 34 2/3 postseason innings that year, including 15 1/3 frames of one-run ball to earn two wins as part of a World Series triumph over the Cardinals.
Ticketed for free agency after the 2014 season, Lester began the year stellar as ever. He tossed 143 innings with a 2.52 ERA for the Red Sox, earning his third career All-Star nod in the process. Yet with free agency looming and the Red Sox on their way to a last place finish, they traded him to the A’s at the deadline. Lester continued to excel over his final few months in Oakland, eventually getting the nod in the AL Wild Card game. The A’s were knocked off by the Royals in one of the more thrilling back-and-forth contests in recent memory, and Lester hit the open market for the first time shortly thereafter.
Ranked by MLBTR as that offseason’s #2 free agent, Lester commanded a six-year, $155MM deal with a Cubs team looking to emerge from a massive rebuild. That’ll go down as one of the best free agent investments in franchise history, as he picked up right where he’d left off upon switching to the National League.
Lester worked 205 innings of 3.34 ERA ball his first season, helping Chicago to the NLCS. The following year, he compiled a 2.44 mark across 202 2/3 frames. He finished second in NL Cy Young voting, earned a fourth All-Star nod, and was arguably the top pitcher on a 103-win team. As he had so often in Boston, Lester shined in the playoffs yet again. He was tabbed that year’s NLCS MVP after tossing 13 innings of two-run ball to knock off the Dodgers. Lester made three outings with a 3.68 ERA during the World Series, in which the Cubs erased a 3-1 deficit against the Indians to end the franchise’s legendary 108-year title drought.
The third World Series title of Lester’s career proved to be his final one, as the Cubs never had quite the same level of success from that point forward. That wasn’t much fault of the veteran southpaw’s, though, as he remained effective for the next few seasons. He paced the NL with 18 wins in 2018, earning another All-Star nod in the process. As he entered his late-30s, Lester’s production finally began to tail off, although he remained remarkably durable and took the ball every fifth day through the expiration of his contract after 2020.
Last winter, Lester hooked on with the Nationals on a one-year, $5MM deal. He made 16 starts with Washington before being flipped to the Cardinals at the trade deadline. Despite lackluster strikeout and walk numbers, he managed a decent 4.36 ERA over 12 starts in St. Louis, proving to be a much-needed stabilizing force for a Cardinals rotation that had been hit hard by injuries. St. Louis made a miraculous September run to a playoff spot, but they fell to the Dodgers in the Wild Card game. Lester didn’t appear in what’ll go down as the final contest of his career.
One of the league’s most reliable hurlers for more than a decade, Lester leaves a fantastic legacy in the game. He tossed 2,740 innings over parts of 16 MLB seasons. He pitched to a 3.66 ERA, won exactly 200 games and struck out just under 2,500 batters. The five-time All-Star was a key contributor to three World Series teams with two separate franchises, and he’ll be remembered by both Red Sox’s and Cubs’ fans as one of the more impactful players in each organization’s recent histories. Lester’s career was valued at between 44 and 46 wins above replacement by FanGraphs and Baseball Reference, before accounting for an incredible 2.51 ERA over 154 playoff innings. According to B-Ref, he earned just over $188MM.
Lester will likely garner some Hall of Fame support five years from now. Whether or not he’s ultimately enshrined in Cooperstown, there’s no question he had a long run of excellence and reliability. MLBTR congratulates Lester on his fantastic career and wishes him all the best in his post-playing days.
Rest In Peace
Congrats on a great career. Personally don’t think he’s HOF worthy but you know what? After going to his baseball reference page, his numbers aren’t anything to sneeze at. Lester’s not the kind of guy who jumps to mind when you think of Cooperstown but man, he’s gonna hang around on the ballot for a bit with those numbers.
Hall of very good.
Really? Look at his career again. Tell me in the modern era the list of pitchers who have or are close to achieving what this man has done. Moreover, Lester is a cancer survivor.
I don’t know what “achieving what this man has done” even means, or what your criteria are for defining “the modern era,” but intentional ambiguity aside, Kershaw, Scherzer, Greinke and Verlander are all contemporaries of Lester’s, and all have much, much better HOF resumes.
I don’t think anybody could argue Lester is a HOFer. Unless they are very, very biased towards him for some reason.
HOF induction is not always a measurement of greatness. This guy had a great career, something he and the fans of teams he spent years playing for can be very proud of.
Statistically no, but WS wins with Red Sox and Cubs might push him over.
I was thinking the same. If I were filling out a ballot and their wasn’t 10 clear HoFers on the list you see him and the narrative around him and think he has to be included on a fair number of ballots. The dude beat cancer in his early 20s to go on to be one of the most durable pitchers in the game over the course of his career and was incredible enough in the post season to help break the two most prolific WS-droughts in history. I’d put him on my ballet.
Should winning a WS with those two franchises give him a bigger boost than if they with for two different franchises?
Bert Blyleven did the same thing (Pirates and Twins) over 30 years ago, and it took him almost every chance he had on the ballot before he got in. World Series rings with two different teams is a cool bit of trivia, but it isn’t going to get anybody into the HOF.
ERA+ of 117 doesn’t scream HoF to me but there’s a bunch of worse pitchers in there now. Jack Morris, for example.
A career ERA+ of 117 is within the range of a HOFer. It doesn’t disqualify, but other stats/accomplishments are needed.
Neither was Harold Baines ever taken seriously as HOF material until Reinsdork started crying to Selig about it.
Wonderful comment by Lester as he exits. He had a solid career with some exciting highlights. All the best in his retirement!
A consistently good pitcher who elevated his game in the postseason.
Not a HOFer, but a fine career. Happy trails.
Yeah, he’s someone I could envision in the dugout managing eventually. Wouldn’t surprise me to see him land a pitching coach job somewhere soon… always seems to have the respect of his teammates, coaches, managers, & fans. We sure as hell respected him as an opponent all those years in Boston.
He hung on one year too long and his Cubs deal was ultimately a massive bust and about 1-2 years longer than it probably should have been. He gave the Cubs something like 5 WAR throughout his entire time on the team.
A massive, massive overpay and a bust of a free agency deal.
But he’s a very likable guy, he’s a feel good story after bouncing back from cancer and he made a ton of money, so, you know, good for him.
This man ended the misery of both the Red Sox and the Cubs. how insane is that
The Red Sox misery ended three years early. Try again.
I guess he helped keep the ball rolling but he was nowhere to be found on the 2004 team that beat the curse.
Lester played a big role in 2007 and 2013!
Ironically if not for the union, Lester would have been traded to the Rangers along with Manny for ARod prior to the 2004 season. Sometimes you’re better off NOT getting what you wish for.
This isn’t an article about Theo Epstein.
Really solid career with many memorable moments. A few commenters seem to be angry with him, but I can’t understand why. Definitely not Hall-worthy, but so what? Interesting he retired just 12 K’s short of 2500.
200 wins in the nose, great career
Thanks for everything you’ve done for the Cubs!
Thanks for the great years in Boston, we will always love and appreciate you! Great career!
Nice career. Glad to see he got to a nice round number with 200 wins
Very nice career.
Lester is right on the borderline for HOF for me. Part of it I think is pulling back the magnify glass. Lester was the ace on 2 World Series teams…and not only that, he gave legendary postseason performances. That going along with his numbers on the lower end of HOF worthy, but with his numbers as a modern pitcher being some of the best of this generation…I think he gets the call down the road, by some kind of modern day veteran committee.
No Lester no ring in Chicago. Was a great free agent signing. Even in his last year Cubs won the division. He had dead arm the last two years in Chicago. I believe they sent him to the disabled list for it once. His performance suffered. Scherzer? Trillionaire team operator Mets fan? Lol.
One of my favorite players of all time. Played a big part in the sox 07′ WS, they wouldn’t have won without him in 2013 and he indirectly netted Rick Porcello who the sox wouldn’t have won a WS in 2018 without and he also won a CY young. THANK YOU JON LESTER!
Pretty sure his results last year were telling him it’s time to go. But you wouldn’t get that from his statements. Either way, great career. Especially when he overcame cancer while in his prime.
So wished he would have come back to boston for 1 year. Between Lester and hill, the sox might have had 2 lefties that could combine to get their #5 spot for 162 games
Oh man, what can I say? As a Cubs fan, I respect the hell out of this man. He was the epitome of an ace, and as the article points out, was at his best when the chips were down. I will never forget what Lester did for my Cubs, and I wish him all the best in retirement. My neighbor’s kid had leukemia and got to meet Jon as part of the Make a Wish foundation. He said that Lester was just as great of a human being as he was a pitcher. Thank you Jonny for all you did both on & off the field.
A winner on and off the field.
Congrats to Jon. He’s likely not a HOF, but should definitely get some votes.
Good career but I don’t think he makes it to the HOF. With that said, I wouldn’t be surprised if they did elect him out of emotional reasons. It’s not like they haven’t done that in the past or allowed guys into the HOF who really shouldn’t be there.
I’m looking at you:
Freddie Lindstrom. Chick Hafey. Jesse Haines. George Kelly. Travis Jackson. Dave Bancroft.
He falls in the Cone, Gooden, herschser, Kevin brown category. Really nice career but not a hof’r
Even those guys all had elite peaks. Lester has never been the best pitcher in baseball, even for half a season. In twenty years is anyone going to say “ya know son, I remember the time I got to see Jon Lester pitch a game?” I doubt it.
Ted–I’m sure there are thousands in Chicago and Boston that will. Nothing better than a Jon Lester fist/glove pump after a huge out to end an inning as he is walking off the field.
Fairly certain Oakland A’s fans aren’t awake, yet. Otherwise the comments would be flooded with sarcasm about the ESPN article referring to Lester as “the best playoff pitcher ever.”
I blame Al.
Every team needs a Jon Lester in the postseason
Very good career. Idk about HOF, but still a fierce competitor and good career.
One of the best postseason pitchers of our era I’ll add!!!
A HOF’er, but he couldn’t throw to first. He had many very notable events in his career. Congratulations Mr Lester on a great career.
congrats
He should’ve finished with the Cubs or Red Sox.
I don’t know about finishing up there, but it would have been nice to see Lester suiting up as a Mariner at some point.
Yeah that’s true. He’s from Tacoma that would’ve made sense.
His no hitter returning from his cancer scare remains one of the great Red Sox moments of all time, from Orsillo’s call (“as Red Sox Nation stands as one for John Lester”) to Francona running out of the dugout crying like a baby. An amazing moment.
I wouldn’t call Lester a HOFer but he had a consistent career.
He had a .631 career winning percentage. Won 203 and lost 111. That is pretty good for a guy who never had a 20+ win season.
In the argument with Fisk and Hurst for stupidest home grown FA the Red Sox let leave.
Great career Jon! Congrats on all you accomplished these many years! Here’s to hoping the rest are even better for you:)
All hail Jon Lester. Loved watching this guy pitch – all the best, Jon.
Lester pitched to exactly a .636 winning percentage and 3.64 ERA in each of his nine total years in Boston and six total years with the Cubs. That’s consistency.
Tim Hudson is currently polling at less than 5% on the HOF ballot. I think he should get more support, but he is likely one and done. I suspect Jon Lester will get a little more support simply because he was on bigger market teams, but wasn’t any better than Hudson over his career.
Lester will probably make the Hall of Fame. But will he do a Q & A with mlbtraderumors
Thanks for helping bring a World Series to Wrigley Field Jon!
Enjoy retirement!
Had the pleasure to see his last game at Fenway in a Red Sox uniform, July 20, 2014 vs KC at Fenway. He has since outlived the opposing pitcher.
He had an amazing pitching performance in game 5 of the 2013 WS.
I will never forgive Ben Cherington and Lucchino for the trade.
That was on Larry. Jon’s opening offer was “they will have to tear this uniform off my back”. Larry’s counter-offer was to rip the uniform off his back.
When it comes to top players seeking 9-figure contracts, the owner always has final say.
Just like I remind people that Henry gives Bloom a budget to work with, same deal with Ben. The Sox lowballed Lester for two reasons:
1) They had just won the World Series, so they knew there wouldn’t be much fan or player backlash if Lester left.
2) Lester made it very clear he didn’t want to pitch anywhere else, so the Red Sox assumed he would take a team-friendly deal just like Arroyo and Pedroia had done.
Great career with two great Teams that he enjoyed three championships with and I believe he will be enshrined into the Hall of Fame by the veterans and deserves the nod with the career he had.
I see him becoming a pitching coach and helping a team like the Cubs develop homegrown talent which will help his Hall chances down the road.
This guy used to own the blue jays when he was on Boston.
Anyone who buys beers for the fans as part of their going away should be 1st ballot HOF. Ok maybe not but wow this guy was the epitome of class for the Cubs and Red Sox organizations.
Helluva career, helluva story. Should be in the hall of very good but probably gets enshrined when you consider everything.
No matter where you place him, he was THE guy you didn’t want to face when your team needed a win in October for a very long time. Amazing to think he pitched 16 years after a cancer diagnosis. Again, just a great story for a great career
I think your initial comment is the one that’s off the mark. I’m sure for Lester, the current environment helped him make his decision…but I think it’s less of that and more that he’s in his late 30s and he’s ready to hang it up.
Bonafide basa$$
Also came to the NL as one of the worst hitters in history and turned himself into a (relatively) tough out.
100% Cubs HOF.
“Came to the NL as one of the worst hitters in history”
John Burkett: “hold my beer”
First-ballot Hall of Very Good, for sure.
I like Full House only when I’m playing poker.
Also had the best pickoff move I’ve ever seen.
I kid, I kid. Congrats to Lester on a terrific career.
Even though he only led the league in wins and hits given up once, he has had a Hall of Fame Career. 40 WAR might not be hall numbers (I believe 60 WAR is the avg, but players like Maz though huh) the consistency of success year after is hard to ignore. One of the last of his kind to go out on the mound and have enough stage presence and success to tell his manager to take a hike when they come to pull him. Once Verlander, Kershaw and Max are done the kids don’t stand a chance in this cancel world. Even throwing one of the best games of your life in the world series still gets you pulled. Way to go Cash, Blake should of told that dude to take a walk. He was gone from the team in the off season anyways. Every team would of enjoyed lesters success.
Ron—excellent point about Verlander, Max, and Kershaw—once they are done everything changes.
What starting pitcher that broke in recently is going to get close to 200 wins? Buehler? He has 40 through 3.5 years…….probably not.
Heck, Lester finished with 200.wins
Verlander has 226
Max has 190 (and age is within one year of Lester)
Kershaw has 183 (still younger, but health could be an issue)
I think it’s a much closer call to the Hall than others. The only thing that separates especially Verlander and Max is the power and strikeouts.
Lester is certainly a tick below those guys but is every bit as good as Schilling (even though Schilling’s career was four years longer)..
I thought you were talking about Mark Buehrle, who definitely deserves to be in the HOF himself. Not sure if hes still on the ballot or not. Almost 60 WAR career himself. Took a long time for Jack Morris to get in the Hof,last year he was eligible I believe. Pitchers like Jack got the respect they rightfully deserved while playing. Once retired, not good enough. Hopefully the writers start recognizing this and get guys in that deserve it. BTW, Walker will be a HOF if he goes 12 years at this pace.
Thanks for the No-hitter and 2 championships Jon.
At least he was able to go out on his own terms rather than just fade into obscurity. It was terrible the way the Sox unceremoniously dumped him at the deadline in 2014 for Yoenis Cespedes but that trade basically turned Lester into Rick Porcello who helped win another championship.
Cubs pitching coach Tommy Hottovy better to do a formidable job this season or it is going to be his last. Cubs manager David Ross will put all the pressure in the world to have his buddy Lester back in his team again, as a coach. Lester is very well respected among players.
Jon Lester is the type of ballplayer I think about when I think about the Hall of Fame. He was a bulldog competitor, consistently taking the ball throughout his career and giving his team everything he had in every game. His postseason pitching is nothing short of Hall of Fame level. His character is impeccable. He played the game right. There is nothing about him that is not Hall of Fame. You can quibble about his statistics not being good enough because that’s what everybody focuses on with the Hall of Fame. But baseball is more than statistics. He’s in my baseball Hall of Fame and that’s all that really matters. Good luck Jon Lester!
Lester should have waited for the lockout to end and sign a one day contract with the Red Sox. He should retire with them. It’s too bad they nickel and dimed him in his big free agent year. I despise the Sox but always had a ton of respect for him and Pedroia. They always seemed to put the team and baseball first. I watch players like Gary Sanchez, Aroldis Chapman and Gerrit Cole on the Yankees and wonder why I spend money on tickets. The lone team first player the Yankees have is Gardner and I have watched him constantly have to fight for a spot and deal with underpaying contracts. Ellsbury gets $150m and Gardy had trouble getting $50m. Absolutely baffled when that happened. I wish Hal would sell the team and take Cashman with him.
Congrats to him. Not many guys can say in the modern era that they have a ring with both the Red Sox & Cubs. I could see him years down the line the Veterans Committee putting him in the HOF. And I still think he got robbed in 2016, he should’ve won the NL Cy Young.
Still cant believe he and his agent couldnt work out an endorsement deal with KFC & Budweiser
It’s Boston Market and Samuel Adams FYP
I missed this guy in Boston. Great pitcher, great career.
Lester, Ortiz, Pedroia, Pedro, Nomar, Varitek, Wakefield, and some more. Boy… did I hate those guys but I have the greatest respect for them.
Hall of very good player at his all-time form who I can’t wait to see go based on current form.
Very good pitcher, especially in the postseason. However,there are at least ten guys in the modern era more deserving and still not in the Hall, and most of them don’t belong either.
So… no.
I thought he already retired.
I’m not totally sure if he’s HoF worthy, but he’s definitely someone I wouldn’t be offended by seeing there if he was. Great career, It hurts knowing that the Blue Jays drafted current Red Sox pitching coach Dave Bush ahead of him lol.
That 2nd round of the 2002 draft had some studs drafted out of high school in it: Votto at #44 overall, Lester at #57, and Brian McCann at #64. Then there was future Cleveland Browns quarterback Brandon Weeden at #71 lol.
Class act….Last time he retired he went around Wrigley Field bars and bought everyone a Budweiser.The gentleman spent 50 large on his way out of Chicago .Now that’s a legendary move..
Imagine Lester or Flaherty pitching in the NL wildcard game. The Cardinals win it and go on to face the Giants in the NLDS.
Can’t wait to see him in the HOF. I hope he knows the tickets are $28 to get in.
Wish I were joining him in retirement.
I see many questions about the HOF and honestly when baseball started letting guys like Baines, Edgar Martinez, and Alan Trammell in they made it the Hall of Good so to Lester I say why not they’ve let worse in.
So I gather you also would strongly be against Ortiz making the Hall if they hadn’t let in Trammell and Martinez?
Edgar Martinez? What is your issue with him getting in? Lol. Dude raked
I do not like the Red Sox at all, and I’m not a Cubs fan, but I’ve always respected Jon Lester as a pitcher. Good luck in retirement, you had a nice career.
Does 200 wins and 3 rings get you in the HOF?In todays game pitchers aren’t winning 20 gms at the clip they used too for 120 yrs.Maybe in 25-30 yrs from now,200 wins will be few and far between.I will never understand why teams weren’t running on every pitch he threw.Dude experienced the RedSox & Cubbies World Series droughts come to an end.Made 2 huge metropolis shake the monkey off their backs.
Great player. Loved what he did for the Cubs
Lester-Hall of the Very Good.
Lester was such a great surprise his rookie year and then a hero for beating cancer.
Everything else was just baseball and he loved playing it. Lucky guy and whether anyone votes for him or not, he’s still a lucky guy and someone to be admired for his resilience.
He should be remembered for the pleasure he gave fans with the way he approached the game, the friendships he built within the sport and his tenacity when the chips were down!
He was a guy I loved going to the park to watch and teach my sons about never giving up!.
Fierce competitor. Good luck to him
One of my all time favorite players. Loved what he did for my Sox, and proud of what he did for Chicago. I wish him all the best in his future career.
I thought it was crazy to read Jon Lester and Hall of Fame in the same sentence and then I read the comments and saw that some of you all are actually trying to seriously argue that he should be there.
Have you all gone mad? The guy rankes 149th in Career JAWS for SP. One-hundred. Forty. Ninth.
And before you start saying “blah blah blah different era blah blah blah….”
….Verlander, Scherzer, Kershaw and Greinke all outrank him on that list. By a WIDE margin. So does Roy Halladay. So does Sabathia. So does Johan Santana (whose career ended far, far too early). Tim Hudson outranks him. Cole Hamels outranks him. Mark freaking Buehrle outranks him.
And before you say, “blah blah blah Jack Morris blah blah blah….”
…yeah, I don’t think Morris belongs in the Hall either.
Lester had an excellent career, there’s no doubt, and I am a “Big Hall” person, for sure. But anybody who says he is a Hall of Famer (or even one of the top 5 of his era) really needs an eye test without the rose colored glasses on.