The five-time all-star and three-time World Series champion had been in St. Louis for less than two months when he reached the milestone. Just ahead of the trade deadline, the Cardinals sent outfielder Lane Thomas to the Nationals to acquire the veteran righthander. At age 37, Lester was just 3-5 with a 5.02 ERA in 16 starts for Washington, but the Cardinals needed Lester and fellow newcomer J.A. Happ (who was acquired in a separate deal) to fill an innings void left by injuries to Miles Mikolas and Jack Flaherty.

“I didn’t even look at the stats or what he did in Washington,” Cardinals third baseman Nolan Arenado said. “I don’t have to look at that when it comes to Jon Lester. I think everyone kind of feels the same way. When you get a pitcher like him, you know he’s gonna give you everything he has, and he’s gonna keep you in ballgames. I feel like he’s better on better teams, and teams that are in it, I feel like that’s where he thrives. That’s just who he is. It’s pretty fun to be a part of, because nothing’s too big for him.”[1]

Lester certainly appeared to be rejuvenated by his arrival in the Cardinals’ playoff race. After losing his Cardinals debut on August 3, Lester won each of his next three decisions, including his September 15 start against the Mets when he allowed just two runs over six innings. That victory was No. 199 for his career and put him on the precipice of joining Justin Verlander and Zack Greinke as the only active players with 200 wins.

As Lester sought to become the 119^th pitcher in MLB history to reach 200, the Cardinals were as hot as they had been in years. With the series opener at the NL Central-leading Brewers on September 20, 2021, the Cardinals sought their ninth consecutive win.

Freddy Peralta, a 25-year-old right-hander coming off the first All-Star Game of his career, took the mound for Milwaukee with a 9-4 record and 2.57 ERA. After Peralta struck out Tommy Edman and Paul Goldschmidt to open the game, the Cardinals’ powerful middle of the order caught up to him (Goldschmidt, Tyler O’Neill, and Arenado each would finish the season with more than 30 homers). After O’Neill singled to center, extending his hit streak to nine games, Arenado launched his 33^rd home run of the season to left field. His two RBIs marked his 100^th and 101^st of the season.

“It’s extremely important to get out to a lead, especially against these arms and these teams that we’re facing that are good,” Arenado said, “but at the end of the day, we are just playing solid baseball regardless of whether we are scoring early or not.”[2]

The Brewers answered in the bottom of the second as Avisail Garcia and Luis Urias each homered. After Urias’s blast, Lester retired the next 10 batters he faced. The score was still tied in the top of the sixth when Yadier Molina punched a single through the left side of the Brewers’ infield to score O’Neill and give the Cardinals a 3-2 lead.

In the top of the seventh, Cardinals manager Mike Shildt pulled Lester in favor of pinch-hitter Matt Carpenter to lead off the seventh. The move worked. Carpenter doubled down the left-field line and scored on Goldschmidt’s sacrifice fly to give St. Louis a 4-2 lead. One inning later, Molina singled to left to drive in his second run of the game.

From there, the Cardinals’ bullpen locked the game down. Kodi Whitley, T.J. McFarland, and Luis Garcia each threw a scoreless inning, and Garcia’s save marked his first of the season.

“We hit a bunch of lazy fly balls,” Brewers manager Craig Counsell said. “We didn’t put enough pressure on Lester or the bullpen. It was just a quiet night.”[3]

Lester allowed just three hits on the day while striking out two.

“What a tremendous addition. He’s done a great job,” Shildt said. “This guy’s got such heart. He’s like John Wayne. He’s got that true grit. Big, strong, silent type. That’s a heck of a milestone.”[4]

“It’s a nice round number and it looks better than 199,” Lester said. “It’s obviously awesome, but I’m kind of lacking words.”[5]

Lester was more comfortable talking about the Cardinals’ win streak, which was now up to nine games.

“That makes it even more special,” Lester said. “To add on the fact that that’s nine in a row for us — I don’t think people realize how hard it is to have winning streaks over four, five, six games. They don’t happen a lot. Now that we’re at nine, hopefully we can keep going.”[6]

The Cardinals did exactly that, extending their win streak to 17 games on their way to a one-game wild card playoff against the Dodgers.

Lester’s 200^th win proved to be the last of his career as he received no decision in his final two starts, both against the Cubs. In January 2022, he announced his retirement. After 16 big-league seasons, Lester had compiled a 200-117 record and 3.66 career ERA.

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[1] Ryan Herrera, “Cards roll to 9^th straight in Lester’s 200^th W,” MLB.com, September 20, 2021, https://www.mlb.com/news/jon-lester-gets-200th-win-for-cardinals-in-playoff-hunt.

[2] Rich Rovito, “Lester wins 200^th, Cards down Brewers for 9^th straight win,” Belleville News-Democrat, September 22, 2021.

[3] Rich Rovito, “Lester wins 200^th, Cards down Brewers for 9^th straight win,” Belleville News-Democrat, September 22, 2021.

[4] Rich Rovito, “Lester wins 200^th, Cards down Brewers for 9^th straight win,” Belleville News-Democrat, September 22, 2021.

[5] Rich Rovito, “Lester wins 200^th, Cards down Brewers for 9^th straight win,” Belleville News-Democrat, September 22, 2021.

[6] Ryan Herrera, “Cards roll to 9^th straight in Lester’s 200^th W,” MLB.com, September 20, 2021, https://www.mlb.com/news/jon-lester-gets-200th-win-for-cardinals-in-playoff-hunt.

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