Jon Lester announced his retirement on Wednesday, the end of his decorated 16-season big-league career.
Six of those seasons came in Chicago, where Lester was an integral piece to the Cubs' competitive turnaround after signing a six-year deal in December 2014 — a pivotal moment in the franchise's rebuild.
The Cubs made the postseason in five of the next six seasons, including trips to the NLCS in each of Lester's first three years with the team — one of which resulted in the Cubs' first championship since 1908.
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Lester won 77 games in a Cubs uniform and compiled a 3.64 ERA. He made 30+ starts in each full 162-game season of his tenure, making a pair of All-Star teams while taking home NLCS co-MVP honors in 2016.
He's considered the greatest free agent signing in Cubs history and delivered countless memorable moments in Chicago.
As he heads into retirement, let's revisit some of those moments:
First win
MLB
Lester got off to a slow start with the Cubs. Through four starts in 2015, he held an 0-2 record and a 6.23 ERA. But once the calendar turned to May, he got on track.
Lester picked up his first win as a Cub on May 1, 2015, tossing seven shutout innings against the Brewers. He allowed just three hits and one walk, striking out four.
That outing kick-started a four-start win streak for Lester and was the first of 11 wins for the lefty in 2015.
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Single-game best
Lester struck out 14 Rockies in eight innings on July 29, 2015, his most in a single game with the Cubs.
He struck out six straight at one point, starting from the final out in the first inning through the second out in the third.
While Lester only struck out three batters his next start, he mowed down 10 in the ensuing outing, Aug. 13 against Milwaukee.
Going the distance
Lester threw his first complete game with the Cubs on Sept. 15, 2015, against the Pirates. He allowed one run on five hits, striking out nine with one walk on 111 pitches.
Lester went on to throw three more complete games with the Cubs — two in 2016 and one in 2017.
Grand introduction
Unlike 2015, Lester started the 2016 season in grand fashion. He picked up the win in his first start, tossing seven innings of one-run ball against the Angels, allowing four hits with no walks.
For Lester, the outing was a sign of things to come. He went 19-5 with a 2.44 ERA in 32 starts in 2016, finishing second in NL Cy Young Award voting to the Nationals’ Max Scherzer.
Walk-off bunt
The Cubs trailed the Mariners 6-0 after three innings on July 31, 2016. They evened things at 6 with a three-run ninth inning, and by the 12th inning had the winning run on third base with one out.
Lester played hero, dropping down a pinch-hit, squeeze bunt in front of home plate to bring Jason Heyward home, giving the Cubs a 7-6 victory.
Game 1 statement
Lester was at his best in Game 1 of the 2016 NLDS, a low-scoring affair with Johnny Cueto on the bump for the Giants.
He matched Cueto pitch for pitch, tossing eight shutout innings of five-hit ball. In fact, he was one pitch better than the Giants ace. Javy Báez hit a solo home run off Cueto in the eighth inning in a 1-0 Cubs win.
Most valuable
Lester’s reputation as a big-game pitcher was on display time and time again during his Cubs tenure, especially during the 2016 NLCS.
Lester made two starts against the Dodgers — Games 1 and 5 — allowing two earned runs total across 13 innings. He left Game 1 with the Cubs ahead 3-1 but received a no decision after a late Dodgers rally.
The Cubs eventually won the series opener 8-4, the same score they won Game 5. Lester’s efforts (and some late Cubs offense) put the Dodgers on the brink of elimination, and the Cubs clinched their first pennant since 1945 in Game 6.
Lester and Javy Báez were named co-MVPs of the series.
Staying alive
No one expected the Cubs to fall into a 3-1 deficit in the 2016 World Series. Needing a Game 5 win to stave off elimination, Lester delivered.
Lester threw six innings of four-hit, two-run ball before the Cubs passed the ball off to closer Aroldis Chapman, who slammed the door in innings 7-9 to force a Game 6.
The Cubs signed Lester for moments like this and he lived up to his billing as a big-game pitcher. The Cubs clinched their first championship since 1908 two games later — with Lester pitching three innings in relief.
‘He’s not going to throw to first base’
Lester didn't often throw pickoff attempts. Cardinals outfielder Tommy Pham tried to exploit that on June 3, 2017.
Pham took leads close to 20 feet off the first base bag, daring Lester to throw over. Tim McCarver said of Lester on the St. Louis broadcast: “He’s not going to throw to first base.”
Lester threw to first for an easy inning-ending pickoff in a 5-3 Cubs comeback win.
Have a night
Aug. 1, 2017 was a memorable night on multiple levels for Lester. He became the 25th lefty in MLB history to reach 2,000 career strikeouts, recording nine on the night. He also hit his first career home run, an opposite-field drive.
However, he pitched four innings and received a no decision and was miffed at his performance after the game.
"I'll trade that home run in a heartbeat for a win," Lester said after the game. "That's my job — my job is to pitch deep into games, give innings, give our guys quality starts and then hand it off to the bullpen, and I didn't do that tonight."
Lester hit a home run in each of the next two seasons, a streak snapped in 2020 as MLB instituted a universal DH.
Last playoff outing
The Cubs’ postseason trip lasted just one game in 2018, although Lester turned in another strong playoff performance in the NL Wild Card Game against the Rockies.
Lester allowed four hits and one run in six innings, walking one while striking out nine. The Cubs lost 2-1 in 13 innings.
That turned out to be Lester’s final postseason appearance with the Cubs (and of his career). In 12 appearances (10 starts), he posted a 2.44 ERA.
Final Cubs season debut
Lester’s final season debut with the Cubs came three months later than usual due to COVID-19. He tossed five no-hit innings against the Reds.
Lester exited after throwing 76 pitches as pitch counts were limited early in 2020 following baseball's three-month shutdown due to the pandemic, The Cubs won 8-7.
Bounce back
Lester’s confidence took a hit towards the end of the 2020 season. In five starts from mid-August to early September, he allowed 24 earned runs across 23 1/3 innings.
“I don’t know where the confidence will come from,” he said.
Five days after discussing his struggles, Lester bounced back to throw six innings of three-hit, shutout baseball against the Brewers.
That outing in Milwaukee began a three-start stretch in which Lester allowed two earned runs in 17 innings (1.06 ERA).
Salute
Days after the Cubs declined his 2021 option in October 2020, Lester saluted Cubs fans by buying beers for Chicagoans at four bars during Halloween weekend. His tab added up to over $40,000, before adding in his 34 percent tips — a nod to his jersey number.
Welcome back
Lester returned to Wrigley Field last May for the first time after signing with the Nationals over the offseason. He started the series opener, a 7-3 Cubs win on May 17.
The Cubs honored their former ace the next day, playing a video tribute and giving Lester Wrigley Field-themed gifts, including a W flag signed with personal messages from members of the organization.
200 club
Lester, who the Nationals traded to the Cardinals at the 2021 trade deadline, was nearing a career milestone last September ahead of a Cardinals-Cubs series at Wrigley Field: 200 wins.
He made a start days before that series, and good friend and Cubs manager David Ross found himself in an unfamiliar position.
“I rooted for the red team yesterday, and that felt really strange,” Ross said of the Cardinals.
Lester beat the Brewers to reach the milestone, becoming the 119th pitcher in MLB history and 30th lefty to do so.
That ensuing start at Wrigley was still memorable. Lester and the Cardinals beat the Cubs to extend their winning streak to 15 games, a franchise record that extended to 17.