The peak of Adam Wainwright's career, albeit shortened, has made him one of the most respected pitchers of his generation. The length of his career has done the same -- and made him a marvel to watch.

Whether you call him Waino, Adam or Uncle Charlie, Wainwright has made a name for himself as one of the best and most durable starters of the 21st century. Raised on the old-school mindset of pitching deep into games, Wainwright is central to the Cardinals' winning ways over the past two decades, the artist of the final pitch in the 2006 World Series and a leader on the bench for the 2011 title.

Here are some of the best moments of Wainwright’s career.

1. The two pitches that started it all
Oct. 19 and Oct. 27, 2006

Wainwright was handed the nickname Uncle Charlie for that equal parts deliberate and threatening curveball that has lured countless hitters into befuddlement. That legend?

It started early. Wainwright is synonymous with the Cards’ 2006 World Series triumph for his proximity to the grand moments. In Game 7 of the NLCS in Queens, after Yadier Molina put St. Louis ahead with a two-run blast in the top of the ninth, Wainwright froze future teammate Carlos Beltrán with his patented curve to send the Cards to the World Series. To close Game 5 of the Fall Classic, he whiffed Brandon Inge of the Tigers, this time at home.

Wainwright did it all as just a rookie, thrust into the closer role for the postseason due to necessity and saving four games along the way. Both moments resulted in an embrace with Molina on the mound -- moments that played on repeat in St. Louis.

2. 200th career win
Sept. 18, 2023

In a scene seemingly straight out of a dramatic Hollywood script, the 42-year-old Wainwright turned back time, fought through the pain he felt throughout the night and crafted another career-defining moment to register the 200th win of his career.

Hit hard all season and, at times, embarrassed by performances in which he was shelled by opposing hitters he used to baffle, Wainwright somehow conjured up his best outing of the season to beat the rival Brewers, 1-0, in front of the St. Louis faithful. Over a season-best seven scoreless innings, Wainwright allowed just four hits, and only one batter reached third base all game.

Chants of “Let’s Go Waino!” filled the air in the seventh when he stranded the potential tying run at third base. Close your eyes and you might have sworn it was 2009, ’10, ‘13 or ‘14 -- a stretch in which Wainwright won 19, 20, 19 and 20 games, respectively, and finished in the top three in NL Cy Young voting each time.

Wainwright went 11 starts, 10 losses and 87 days in between wins No. 198 and 199. On a Monday night at Busch Stadium, he won No. 200 on his first try and in the manner he wanted.

“Being able to do it here in front of our home crowd was incredibly special,” said Wainwright, who became the fifth active MLB pitcher with 200 wins and just the third in Cardinals’ history. “I’m glad I got to embarrass myself, crying like a baby on the field. But, you know what, I’m not embarrassed at all. 

“I was happy and proud and overwhelmed. The crowd was unbelievable, and I felt them cheering on every pitch I made and on every strikeout and double play. They were on their feet all night and I felt that.”

3. His most important hardware
Dec. 7, 2020

Two World Series rings (one as a spiritual leader). Three All-Star nods. Two Gold Gloves. One Silver Slugger. But no piece of hardware is more valuable to Wainwright than the prestigious Roberto Clemente Award he received in 2020 for the work his charity, Big League Impact, has done in providing basic resources -- food, clean water, medical care and shelter -- to those in need around the globe. Enriching the lives of others and setting an example for a future generation have been central to both Wainwright the pitcher and the human. Winning the Roberto Clemente Award is chief on that list.

“This is the greatest honor of my entire career,” Wainwright said at the time.

4. The Peak (and The Comeback, Part I)
2009-14 seasons

Wainwright will be an interesting case study for whenever he’s eligible for voting into the Baseball Hall of Fame. Grading by his peak, of which he lost an entire year in 2011 plus added time in 2015, four Top 5 finishes for the NL Cy Young is quite a résumé. That’s the type of dominance that Wainwright enjoyed from 2009-14, his 2.83 ERA and 135 ERA+ ranking third among starters in that span and his 92 wins sitting at fourth. That he’s remained elite into this latter stage of his career will only help his case. And we’re left to wonder what if he didn’t miss an entire year.

Not included among the counting stats of Wainwright’s peak is his role during the 2011 World Series run. Lost in Spring Training after undergoing Tommy John surgery, he has been widely regarded as the spiritual leader and the motivational voice on the bench. And so it became the first major comeback of his career.

5. A franchise-altering trade
Dec. 13, 2003

For as long as Wainwright has been a Cardinal -- the second-most starts and the second-most strikeouts in franchise history thanks to 18 seasons (17 as an active player) -- it’s easy to forget that Wainwright’s professional career started elsewhere. The Brunswick, Ga., native was selected by the Braves (his childhood team) in the first round of the 2000 Draft (the same Draft Molina was selected in) and spent four years in Atlanta’s system before a life- and franchise-altering swap. In one of the biggest trades in the club’s history, St. Louis in December 2003 sent J.D. Drew and Eli Marrero to the Braves in exchange for Ray King, Jason Marquis and a 22-year-old righty with a Minor League ERA under 3.40. He would blossom into one of the most integral pitchers in the franchise’s history.

6. A heralded postseason start
Oct. 9, 2013

With a postseason ERA of 2.83, Wainwright is bound to have a few October gems on his resume. While the 2006 World Series moments stand out as his most memorable, the conversation of his best postseason start centers around 2013, when Wainwright pitched his club to the NLCS with a dominating complete game against the Pirates, working around eight hits, one walk and an earned run to go with six strikeouts. It was a continuation of his dominating regular season, when he led the NL in wins, starts, complete games, shutouts and innings -- a season, by bWAR standards, tied with 2009 as the best of his career. And it was a dominating postseason in total: Wainwright’s Game 5 gem came after seven seamless innings in Game 1 and a 2.57 ERA that October in full. His pair of starts in the 2013 Fall Classic are the only World Series starts of his career thanks to the injury sustained in 2011.

7. The Comeback, Part II
May 13, 2018

When Wainwright departed the Petco Park mound on this May afternoon due to injury -- he’d later say his right elbow was in so much pain that he could feel his bones scraping against one another -- he thought his career might be over. But with the encouragement of teammate Dominic Leone, also rehabbing at the Cards’ Spring Training facilities from a serious injury, Wainwright felt compelled to attempt a comeback. So he altered his diet, changed his approach, tweaked his delivery and overall refined the early-career process that made him an ace but needed to change as he aged. This moment encapsulates Wainwright’s late-career renaissance; to the groans of some disbelievers, he returned for four starts in September. In five seasons since, Wainwright has posted a 51-43 record, a 4.13 ERA, six complete games (one shutout), a seventh-place Cy Young finish and revived a career that was once on life support.

8. An enduring partnership
April 6, 2007 to Oct. 2, 2022

The careers of Molina and Wainwright are inexorably linked. With 328 starts together, the duo boasts the most starts as batterymates in AL/NL history. From their first start together on April 6, 2007, the story of the 21st-century Cardinals cannot be told unless it starts with Wainwright and Molina. They have become immortalized for the moments they shared, embraces on the mound to close out both the 2006 NLCS and World Series. The only question is if their statues outside Busch Stadium will stand 60 feet, six inches apart.

• Waino-Yadi partnership in ranks with legends

9. A boom of a beginning
May 24, 2006

Maybe the award Wainwright cherishes second to his Roberto Clemente hardware is the Silver Slugger he won in 2017. After the first at-bat of his career, it might be surprising he doesn’t have more. Exclusively a reliever in his rookie season, Wainwright had to wait until his 14th appearance for a chance at the plate. In the midst of a three-inning outing, he led off the fifth inning and promptly sent the first pitch he saw to deep left field in San Francisco. It’s a moment he remembers fondly, and one he now wishes he had the Statcast data on. All told, Wainwright is one of just three players in AL/NL history to homer in his first at-bat then win the game as a pitcher. He later grounded out for a ho-hum 1-for-2 day at the plate.

10. Finally, a Maddux
Aug. 12, 2021

In Wainwright’s brief time with the Braves, he was a disciple of Hall of Famer and Atlanta great Greg Maddux. The two talked pitching -- not throwing -- and how to be a competitor on the mound. For Wainwright, a Georgia native, it was an inspiring opportunity.

But it took Wainwright 16 years into his Major League career to accomplish the feat named after his childhood idol, a shutout thrown on fewer than 100 pitches. When it finally came under the guide of pitching coach Mike Maddux, Greg's brother, and in a ballpark that he struggled at early in his career, it was fulfilling -- not just because of the feat in and of itself, but because he accomplished it just weeks before he turned 40.

11. 2,000 and counting
Sept. 23, 2021

The longer Wainwright has pitched, the more his counting stats become all the more impressive. When he whiffed Luis Urías after an epic eight-pitch battle in Milwaukee, he had an exclusive one: 2,000 strikeouts, becoming the 85th pitcher in AL/NL history to do so.