Jon Lester Cubs
David Banks-USA TODAY Sports

Former Boston Red Sox and Chicago Cubs lefty Jon Lester has retired from baseball.

Veteran lefty and longtime New York Yankees nemesis Jon Lester has retired from baseball, according to ESPN’s Jesse Rogers.

As both a New York Yankees fan and sportswriter who covers them, this is certainly bittersweet. Jon Lester began his career with the rival Boston Red Sox as a fresh-faced 22-year-old in 2006 and soon became a rotation staple. Two years later, he threw a no-hitter.

Not to mention, Lester’s rookie year was cut short when he was diagnosed with lymphoma and had to undergo treatment immediately. He returned in 2007 and won the first of three World Series rings, the last being as he helped the Chicago Cubs break their century-long curse.

200 wins. A 3.66 career ERA. 16 MLB seasons with five teams. Jon Lester was never an elite pitcher, but he was a consistent and reliable lefty arm. He got the ball and everyone just knew that win or lose, he was going to bring his best.

The New York Yankees learned this lesson one too many times. Lester went 13-6 with a 3.68 ERA in 30 career starts against them, and across 181 innings. That’s a pretty solid single season once you add all the numbers.

In Yankee Stadium, however, Lester fared even better. 18 starts, a 10-3 record, and a 3.29 ERA.

Oh, and how about a 2.57 ERA in the postseason? Again, not an elite pitcher, but a reliably consistent one.

Now, at age 38, Jon Lester is calling it a long, beautiful, and successful career. He spent his final season with the Washington Nationals and St. Louis Cardinals, going 7-6 with a 4.71 ERA.


JB’s Take

Few will remember, but Jon Lester was truly one of a kind. He took the mound in his prime and all that opposing hitters could do is hope they caught him on a bad day. Even when some of the more idiotic Yankees fans shouted cancer-ridden comments from the bleachers, Lester’s stoicism matched that of the great Andy Pettitte.

Cool. Calm. Collected. One game, one goal, win. Even as he got older and injuries became a new normal, he’d every so often flash that vintage flair and remind us who he was.

That said, is Jon Lester headed for Cooperstown? It’s hard to say with his numbers but given today’s standard, it’d be hard to not vote him in. Needless to say, this proud New York Yankees man would gladly cast that ballot.

Happy retirement, Jon. You’ve more than earned it.

Josh Benjamin has been a staff writer at ESNY since 2018. He has had opinions about everything, especially the Yankees and Knicks. He co-hosts the “Bleacher Creatures” podcast and is always looking for new pieces of sports history to uncover, usually with a Yankee Tavern chicken parm sub in hand.