Red Sox: The five biggest moments of Jon Lester’s career in Boston

BOSTON, MA - JULY 20: Jon Lester #31 of the Boston Red Sox reacts after walking a man in the sixth inning against the Kansas City Royals at Fenway Park on July 20, 2014 in Boston, Massachusetts. (Photo by Jim Rogash/Getty Images)
BOSTON, MA - JULY 20: Jon Lester #31 of the Boston Red Sox reacts after walking a man in the sixth inning against the Kansas City Royals at Fenway Park on July 20, 2014 in Boston, Massachusetts. (Photo by Jim Rogash/Getty Images)
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NEW YORK, NY – JUNE 28: Jon Lester #31 of the Boston Red Sox looks in to the catcher before he delivers a pitch against the New York Yankees during the fifth inning in a MLB baseball game at Yankee Stadium on June 28, 2014 in the Bronx borough of New York City. (Photo by Rich Schultz/Getty Images)
NEW YORK, NY – JUNE 28: Jon Lester #31 of the Boston Red Sox looks in to the catcher before he delivers a pitch against the New York Yankees during the fifth inning in a MLB baseball game at Yankee Stadium on June 28, 2014 in the Bronx borough of New York City. (Photo by Rich Schultz/Getty Images) /

Former Red Sox southpaw Jon Lester calls it a day

While the rest of the baseball world is frozen there was a bit of news that came down the pike today. Former Red Sox lefty Jon Lester has decided that it was time to hang up his cleats. The big man from Washington has had one hell of a career and he has nothing to be ashamed of when he looks back at his body of work.

Lester was drafted by Boston in the 2022 draft and would eventually make his debut in 2006. It was also in 2006 that he was diagnosed with Lymphoma, costing him much of his rookie season and half of the next. He never flinched though and merely put his head down and pushed through the adversity en route to getting back to his team.

In 16 years as a Major League pitcher, Lester has won three World Series titles, was a five-time All-Star, owns an NLCS MVP honor, and has amassed 200 wins in 2,740 innings of work with 2,488 strikeouts. He was a key member of the pitching staff for Boston, Chicago, Washington, Oakland, and St. Louis.

While he’s done plenty of work for those other clubs we’re here to look at what he did with the Red Sox. With that said, these are the five biggest moments of his tenure in Boston.

Boston Red Sox pitcher Jon Lester (31) pitches for the Greenville Drive at West End Field in Greenville Monday, April 9, 2007. Lester is scheduled to make a total of four starts for Greenville following treatment of lymphoma. KEN OSBURN/Staff Boston Red Sox Pitcher Jon Lester
Boston Red Sox pitcher Jon Lester (31) pitches for the Greenville Drive at West End Field in Greenville Monday, April 9, 2007. Lester is scheduled to make a total of four starts for Greenville following treatment of lymphoma. KEN OSBURN/Staff Boston Red Sox Pitcher Jon Lester /

Jon Lester returns to the Red Sox after beating lymphoma

This is easily the biggest moment of his life, let alone his playing career. When it was announced that he was going to be leaving the team in 2006 to begin his battle with lymphoma I doubt anyone thought he’d wind up having the type of career that he did. That is, everyone except Jon.

The lefty would work through every level of the Minors in 2007 to build up his strength and endurance to an eventual return to the Red Sox. That day would eventually come in July as he was set to make his season debut against the Cleveland Guardians at Jacobs Field. On that night, Lester would toss a stellar six innings of two-run ball, striking out six and walking three.

“I was in Triple-A on a rehab assignment in Pawtucket after cancer,” Lester told ESPN.com. “My parents were there and they were leaving that day or the next day to go home, and I told them they have to change their flight. I said I’m starting the next night in Cleveland.”

I don’t think you could’ve asked for anything more from the then 23-year-old pitcher coming off of the biggest fight of his life. We all know how 2007 ended for the Red Sox and Jon was a massive part of that success. He would finish the season with a 4-0 record, 4.57 ERA, 63.0 IP, and a 1.61 K/BB. Don’t worry though, I’ll be highlighting what he did in October of that season next.

DENVER – OCTOBER 28: Starting pitcher Jon Lester #31 of the Boston Red Sox warms up in the outfield before Game Four of the 2007 Major League Baseball World Series against the Colorado Rockies at Coors Field on October 28, 2007 in Denver, Colorado. (Photo by Stephen Dunn/Getty Images)
DENVER – OCTOBER 28: Starting pitcher Jon Lester #31 of the Boston Red Sox warms up in the outfield before Game Four of the 2007 Major League Baseball World Series against the Colorado Rockies at Coors Field on October 28, 2007 in Denver, Colorado. (Photo by Stephen Dunn/Getty Images) /

Jon Lester earns the Red Sox another World Series title

In something that has become a bit of a routine for Red Sox Nation nowadays was still a bit of a shock back in 2007. The team was just one win away from a World Series championship, the team’s second in four seasons. Getting the call that night, Jon Lester. Hell, he beat cancer, starting a World Series game should be a breeze, and he sure made it look that way.

Game 4 of the ’07 Fall Classic saw a pitching duel between Lester and Aaron Cook. While many will talk about Dustin Pedroia and Jacoby Ellsbury absolutely going off against Colorado, this night belonged solely to Lester. He turned a white-hot Rockies club ice cold in a manner that you’d never know he was starting his first-ever Postseason game.

The legend of Jon Lester in October truly began on this night as he pitched for 5 2/3 innings giving up just three hits and three walks while also striking out a trio. He went out there that night in Colorado and gave his team everything that he had in what was an incredibly emotional start. His start allowed the Red Sox to raise the Commissioner’s Trophy on that night and he’d earn his first of three rings.

BOSTON – MAY 19: Jon Lester #31 of the Boston Red Sox reacts after throwing a no hitter against the Kansas City Royals at Fenway Park on May 19, 2008 in Boston, Massachusetts. (Photo by Jim Rogash/Getty Images)
BOSTON – MAY 19: Jon Lester #31 of the Boston Red Sox reacts after throwing a no hitter against the Kansas City Royals at Fenway Park on May 19, 2008 in Boston, Massachusetts. (Photo by Jim Rogash/Getty Images) /

Jon Lester throws another Red Sox no-hitter

For a period of time, it wasn’t a shock to see a Red Sox pitcher toss a no-hitter. While Jason Varitek was the backstop of the club he managed to catch a record of four no-hitters. In 2008, Jon Lester added his name to Varitek’s growing list in what would be notch number four on the belt. This was also Jon’s first full season and he didn’t disappoint whatsoever.

In this day and age, a pitcher’s record isn’t as important but I can’t gloss over his 16-6 tally for Boston that season. He’d also finish the season with a 3.21 ERA through 210 1/3 innings of work. He’d also improve his K/BB ratio up to 2.30 while also leading the American League with a pair of shutouts.

Kansas City was in town on this May evening and boy was the southpaw feeling it. Varitek helped Lester navigate the waters and kept the young hurler cool, calm, and collected throughout the night.

He would sit down nine Royals on the night while allowing just a pair to get on base thanks to the free pass. Just think about that. He was two walks away from a perfect game, damn.

With two outs in the top of the ninth inning, he was able to get Alberto Callaspo to swing and miss to seal the deal and complete the no-hitter. In an instant, he threw his hands into the air in elation as Varitek charged the mound to celebrate.

The most emotional part of the night was seeing Terry Francona, with his eyes full of tears, hug his young pitcher and some words of pride. It was an absolutely beautiful thing to see from the first pitch to the final out.

BOSTON, MA – OCTOBER 30: Jon Lester #31 of the Boston Red Sox celebrates with his son Hudson and wife Farrah Stone Johnson after defeating the St. Louis Cardinals 6-1 in Game Six of the 2013 World Series at Fenway Park on October 30, 2013 in Boston, Massachusetts. (Photo by Jamie Squire/Getty Images)
BOSTON, MA – OCTOBER 30: Jon Lester #31 of the Boston Red Sox celebrates with his son Hudson and wife Farrah Stone Johnson after defeating the St. Louis Cardinals 6-1 in Game Six of the 2013 World Series at Fenway Park on October 30, 2013 in Boston, Massachusetts. (Photo by Jamie Squire/Getty Images) /

Jon Lester leads the Red Sox in the 2013 Postseason

Earlier in this slideshow, I mentioned the legend of Jon Lester in the Postseason, and in 2013 he cemented it. No longer was he a young pitcher early in his career. Now he’s a veteran on a roster filled with them and he’s one of the leaders in the clubhouse.

While many had soured on him after the chicken and beer incident of 2011, he more than redeemed himself in 2013.

In what would be his final full season with the Red Sox, the lefty went out and emptied the tank from Opening Day to the final out of the World Series. And that’s what this one’s all about, his efforts in that final Boston October run.

He put in work in all three levels of the playoffs that season making sure that he would give the Sox their best chance at another ring.

When all was said and done and the champagne was being poured all over Fenway Park, he would own a 4-1 record in the Postseason with a 1.56 ERA, 29/8 K/BB split, while giving up just six earned runs over 34.2 IP.

That’s just an insane line and it really showed that he could be a big factor for this team going forward, unfortunately, we didn’t know it then but his days with the organization would be numbered.

BOSTON, MA – MAY 3: Jon Lester #31 of the Boston Red Sox makes the assist on a ball hit back to the mound by Coco Crisp #4 of the Oakland Athletics in the sixth inning at Fenway Park on May 3, 2014 in Boston, Massachusetts. (Photo by Jim Rogash/Getty Images)
BOSTON, MA – MAY 3: Jon Lester #31 of the Boston Red Sox makes the assist on a ball hit back to the mound by Coco Crisp #4 of the Oakland Athletics in the sixth inning at Fenway Park on May 3, 2014 in Boston, Massachusetts. (Photo by Jim Rogash/Getty Images) /

Jon Lester sets a career-high in his final season with the Red Sox

It’s May in 2014, just a few years after his no-hitter in that very month and just months removed from winning his second World Series ring. Jon Lester is on the mound against Oakland and it’s a beautiful day at Fenway Park.

None of us knew that he would soon be playing for these very Athletics in a few short months but on this day, he made them regret coming to Boston.

Jon took the ball this afternoon and seemingly never gave it back. He would give the Red Sox eight strong innings of work and at the end of the day, he’d be walking away with a career-high 15 strikeouts. While his career took him to several other teams where he also achieved great things, this mark still stands for the lefty.

It was no secret that Lester wanted to remain with the Red Sox and finish out his career in Boston, but the owners took his kindness too far. John Henry and the fellas lowballed the lefty with a disgusting four-year.$70M contract offer that was never going to fly.

Then they came up with the great idea to trade him to Oakland as Boston’s season was declining with the hopes of bringing him back in free agency that winter. Yeah, because that always goes well, idiots.

He never should’ve been traded and the Red Sox let one of their few homegrown pitching talents get away without even putting up a fight. I do find it a bit romantic that he would set a career mark against a team that he would be fighting for in just two months’ time. Lester’s efforts were almost ruined as Chris Capuano served up three runs to the A’s in the top of the ninth before Koji Uehara came in and slammed the door shut.

Jon Lester was one hell of a pitcher and one hell of a person from everything you’ll see, hear and read. Whether it be from his coaches, teammates, or those he’s helped in his communities, he’s earned and deserved all the goodwill he receives. Not only was he a giant on the field but off of it as well.

After 16 years of stellar baseball, I think he can walk away with his head high. I can’t wait for his name to show up on the ballot in a few years and we can praise him all over again.

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