Jon Lester announced his retirement this week. The decision was understandable, and Lester told ESPN’s Jesse Rogers that he knew it was time to go. The proud Lester wanted to leave on his terms instead of scrounging for a job and probably setting himself up for a sad ending to his career.

Here’s a sentence that I never thought I would write, even as Lester joined the Cardinals following a late-July trade from Washington last summer:

The fan in me absolutely loved watching Jon Lester pitch for the Cardinals.

As I wrote recently here at “Scoops,” Lester’s important closing chapter in St. Louis was high on my list of favorite highlights of the 2021 season. This is why we’re still so fond of sports, even through the many disappointments. We stay with it because of the people, the stories, the unexpected plot twists. We come back for the good times, the chance to celebrate sweet moments, and the possibility of witnessing something we thought we’d never see.

I didn’t think I’d ever see Jon Lester pitching for the Cardinals.

And it became a pleasure.

And a fond memory.

Who would have guessed? Lester’s arrival in St. Louis was surprising and confusing. At the time of the July 30 trade, the stubborn lefty was doing about the best that he could while laboring through an abysmal season for the Washington Nationals. It was ugly, with Lester getting pounded for a 5.02 ERA in 16 starts, and right-handed hitters battering him for a .552 slugging percentage and .993 OPS.

Lester’s toughness was fully intact, and he never ran short on competitiveness. But at age 38, and after nearly 2,900 intense big-league innings (postseason included), Lester was set in his ways, too old to reinvent himself, and left increasingly vulnerable by diminished velocity. Lester was blasted for a 6.53 ERA in his last nine starts for the Nats; clearly the end was near for one of the most accomplished starters pitchers of his time.

To the Cardinals’ good fortune, Lester was rejuvenated during his stay here and finished with a display of strength. After two poor starts in his debut for St. Louis, Lester pitched to a 3.40 ERA over his final 10 assignments, and the Cardinals went 7-3 in his starts. Along with veteran lefty J.A. Happ, Lester stabilized the STL rotation and did his share to push the Cardinals into the NL wild-card game.

The Cardinals were saved, in part, by a longtime nemesis and baseball enemy. If Lester pitched for your opponent, you despised the dude. The respect was there, yes, but it was impossible to actually like him. That wasn’t possible when he pitched in the colors of the Red Sox and Cubs.

But when Lester became part of the Cardinals Family – and became friends with former rivals – he was a comfortable fit, and a welcome presence.

As he settled in as a Cardinal, Lester’s stale pitching approach was modified by Adam Wainwright, Yadier Molina and pitching coach Mike Maddux. Lester became more effective. The team’s gold-plated defense was a huge plus for Lester and kept his ERA down.

Lester the Redbird worked out well for all involved. Cardinals fans embraced him. We looked forward to his starts. And It was an unexpected night of joy to see Lester earn career victory No. 200 in a Cardinal uniform.

No. 200 meant a lot to Lester and made it more comfortable to retire. He was a Cardinal for two months. He helped the team reach the postseason for the third consecutive year. The team helped him become a better pitcher.

It was a win-win arrangement that benefited both sides. Lester and the Cardinals – and by extension St. Louis fans – had fun being teammates.

It was just an all-around satisfying experience. I don’t think I’ll ever forget the vision of Molina hugging Lester, holding him tightly, then presenting the pitcher with the game ball from No. 200 after the win at Milwaukee.

“Playing with Waino and Yadi was awesome,” Lester told ESPN.com. “It was a cool experience to play for that organization. You learn to understand why they’re so successful every year.”

Question: Does Lester have the career credentials for induction into Cooperstown? He’s an interesting case. Lester falls short at multiple checkpoints including the Hall of Fame Standards at Baseball Reference, the JAWS Hall of Fame evaluation system devised by Jay Jaffe, and the Hall of Fame Monitor developed by Bill James. The average WAR for a Hall of Fame starting pitcher is 73.0, and Lester doesn’t come close to that with his 44.2 career WAR. Lester didn’t win any major awards, and didn’t lead the league in the most hallowed statistical categories.

That’s the reality and it works against him. But parts of Lester’s career require extra focus. He shouldn’t be judged solely based on the usual standardized tests that make or breaks Cooperstown cases.

Here are a few pro-Lester points to consider:

– Lester pitched for three World Series champions: the 2007 Red Sox, 2013 Red Sox and 2016 Cubs. He was part of 10 different postseason teams during his career. Lester had a 2.51 ERA in 154 career postseason innings covering 22 starts and four relief appearances.

– Lester worked 35.2 World Series innings, going 4-1 with a 1.77 ERA. He started the series-clinching game and shut out the Rockies for 5.2 innings as the Red Sox completed the four-game sweep. In the 2013 World Series against the Cardinals, Lester went 2–0 and allowed one run in 15.2 innings. He pitched three times for the Cubs in the 2016 World Series, starting twice (1-1 record) and contributing three strong relief innings in Chicago’s historical Game 7 triumph.

– Until Lester came to Chicago on a six-year, $155 million free agent contract before the start of the 2015 season, the Cubs hadn’t won the World Series since 1908. Lester, recruited specifically to be the leader of the new-look Cubs pitching staff, delivered on the investment with a 77-44 record and 3.64 ERA. The Cubs ranked second in the NL and third in the majors with a .580 winning percentage in Lester’s six seasons and made it to the postseason five times.

– When the 2016 Cubs terminated the most famous postseason drought in MLB history, Lester had a record of 19-5 with a 2.44 ERA. In the 2016 postseason Lester went 5-1 with a 2.02 ERA.

– Lester is one of only nine modern lefthanders with 200 wins, a .600 winning percentage and a career ERA that’s less than 4.00 runs. Of the eight other lefties that have delivered on that combination, six are in the Hall of Fame. Another, CC Sabathia, will be eligible for the first time in 2025.

– Lester’s winning percentage, .631, ranks 62nd all-time. His career ERA, 3.66, is superior to that of other Hall of Fame starting pitchers including Mike Mussina, Jack Morris, Red Ruffing, Jesse “Pop” Haines and Ted Lyons.

– Lester’s starting-pitcher JAWS Hall of Fame evaluation score is above that of Catfish Hunter, Jack Morris, Pop Haines, Lefty Gomez and Rube Marquard.

– After recovering from cancer, Lester rejoined the Red Sox late in the 2007 season and allowed two runs in 9.1 postseason innings. From 2008 through 2018 he was tied for second among MLB starting pitchers with 166 wins, second with 354 starts, fourth for most innings, sixth in strikeouts. During those seasons Lester had a 2.55 ERA in 144.2 postseason innings.

— In the 11-season career peak (2008-2018) Lester was named to five All-Star teams, won the MVP of the 2016 NLCS, received Cy Young votes four times, finished in the top four of Cy Young voting three times, finished second in Cy voting two times. In addition he ranked among the league’s top 10 in wins eight times, was in the league’s top 10 for best ERA in five seasons, and in six of the 11 years finished among the league’s top 10 in pitching WAR.

Lester’s career postseason performance set him apart from other very good starting pitchers and should warrant extra consideration when it comes time to review his Hall of Fame resume.

It’s a cliche, but simple numbers can’t encompass the depth of Lester’s total value.

“Any time he had the ball, it was a different feeling as a teammate,” former Boston teammate Dustin Pedroia told ESPN.com. “The power, the way he worked, the will to win. He had great stuff, but his best gift was he found a way to win. That’s something you can’t teach, you can’t coach. It’s a special player that has that. There’s not many.”

Lester was special – and in St. Louis we had the chance to see why. In the 2013 World Series, and during the Cubs’ run from 2015 through 2018. Best of all, we were able to see Lester sporting the Birds on the Bat as he stared down opposing hitters in a money-time drive for the postseason. Lester’s time here was brief, but it mattered, and it’s nice for St. Louis to be a small part of his big-league legacy.

Thanks for reading …

–Bernie

Bernie invites you to listen to his opinionated sports-talk show on 590-AM The Fan, KFNS. It airs Monday through Thursday from 3-6 p.m. and Friday from 4-6 p.m. You can listen by streaming online or by downloading the “Bernie Show” podcast at 590thefan.com — the 590 app works great and is available in your preferred app store.

Follow Bernie on Twitter @miklasz

Bernie Miklasz
Bernie Miklasz

For the last 35 years Bernie Miklasz has entertained, enlightened, and connected with generations of St. Louis sports fans.

While best known for his voice as the lead sports columnist at the Post-Dispatch for 26 years, Bernie has also written for The Athletic, Dallas Morning News and Baltimore News American. Bernie has hosted radio shows in St. Louis, Dallas, Baltimore and Washington D.C.

Bernie, his wife Kirsten and their cats reside in the Skinker-DeBaliviere neighborhood of St. Louis.