The Best Moment Of Jon Lester’s MLB Career

Last week, veteran starting pitcher Jon Lester announced his retirement from MLB.

The southpaw decided to walk away from baseball after an outstanding 16-season career in the majors.

Breaking: Three-time World Series champion and 200-game winner Jon Lester is retiring after a 16-year career, Lester told @JesseRogersESPN. pic.twitter.com/1h0kbvWbKG

— SportsCenter (@SportsCenter) January 12, 2022

During Lester’s 16 MLB seasons, he accomplished a lot.

He’ll forever be a legend in two different organizations — the Boston Red Sox and Chicago Cubs.

He put together a handful of unforgettable moments over the years, and today, we’re going to decide which one takes the cake.

Let’s take a look at some candidates before picking a winner.

Lester’s Return From Cancer In 2007

Lester made his MLB debut for the Red Sox in 2006.

During his rookie campaign, he was unfortunately diagnosed with lymphoma.

The scary development obviously ended his season.

Lester underwent offseason chemotherapy to treat the cancer, and thankfully, it was successful.

By December of 2006, the cancer was in remission.

After courageously winning that battle, Lester was able to return to action for the Red Sox in 2007.

On July 23 of that season, he made his first MLB start since beating cancer.

It was a fantastic sight to see, and to make things even sweeter, he turned in a quality start in his first game back.

Lester tossed six innings of two-run ball while striking out six batters in an eventual Red Sox win.

At the time, nobody knew what sort of iconic career was ahead of him.

Lester’s No-Hitter In 2008

Lester gave Red Sox fans an unforgettable moment in 2008 when he tossed a no-hitter against the Kansas City Royals.

It came on May 19, and it was a special night at Fenway Park.

CALLASPO STRIKES OUT!

JON LESTER THROWS A NO HITTER AT FENWAY!

HE NO HITS THE KANSAS CITY ROYALS! pic.twitter.com/gyL5Y65FJ9

— Brendan Kennedy (@TheSoxBox617) January 12, 2022

In this legendary performance, Lester struck out nine batters and issued just two walks.

The Red Sox came away with a 7-0 win in the game.

Lester was just 24 years old at the time of the no-hitter, and he was visibly overwhelmed with joy after getting the final out.

Many folks in Greater Boston likely felt the same way after watching it unfold on TV.

Interestingly, Lester almost had two no-hitters in the 2008 season.

In addition to his no-hitter against the Royals, he had a game earlier in the season in which he allowed just one hit over eight shutout innings against the Toronto Blue Jays.

Lester’s 3 World Series Titles

Lester won three World Series titles during his career.

Two of them came with the Red Sox, and the third came with the Cubs.

Jon Lester was one of 17 pitchers in MLB history with 200 career regular-season wins and three World Series titles. Eleven of the other 16 such players are members of the Baseball Hall of Fame.

Tell us: what's your favorite Jon Lester moment? pic.twitter.com/53fgbw0qlG

— Elias Sports Bureau (@EliasSports) January 12, 2022

To be a three-time champion is an extremely rare feat, but in Lester’s case, it’s even more special than it appears on the surface.

All of Lester’s titles were exceptionally meaningful in their own way.

His first title came in 2007 with the Red Sox, and as mentioned, that was his first season back from cancer.

He played a crucial role for Boston during the team’s run to the title, and he even got the win in the clinching game of the World Series.

In 2013, he helped the Red Sox win another championship.

Of course, Boston’s 2013 title will always be one of the most meaningful championships in sports history after everything the city went through with the marathon bombing.

Then in 2016, Lester got the final ring of his career, and he did it in style.

He helped the Cubs capture their first World Series title since 1908.

They likely wouldn’t have been able to do it without him.

The Top Moment: Lester Wins 2007 World Series With Red Sox After Beating Cancer

There are so many good options on this list to pick from, but it’s hard for any of them to top Lester’s 2007 title with the Red Sox.

To return from cancer and win the clinching game of the World Series in the same season is an unbelievable accomplishment.

Here’s a look at the final out of that series, which gave Lester the first ring of his career:

On this date in 2007: the Boston Red Sox! Wooooooooo! pic.twitter.com/ITzA9n6SnS

— Honest☘️Larry (@HonestLarry1) October 28, 2021

Folks in Boston will never forget the 2007 title, and Lester had a huge hand in making it happen.