Top 5 moments of Adam Wainwright's Cardinals career

It's sad to think about, but Adam Wainwright's legendary career with the St. Louis Cardinals is ending in less than a week. #50. Uncle Charlie. Waino. Whatever you call him, he has been a mainstay with St. Louis for nearly 20 seasons (18 to be precise). Wainwright officially made his debut in 2005 as a baby face reliever and is calling it quits here at the end of 2023 as a franchise legend.

Though this season hasn't been the greatest for Waino, he was still able to notch that elusive victory #200 and become just the third St. Louis Cardinal of all-time with 200+ wins. After the game on Monday, Wainwright said that this was one of the best moments of his career, and he's had a lot of moments. So I wanted to take a moment of your time, dig in, and look back at some of the top moments of Adam Wainwright's career.

*Honorary* Win #200 - 09/18/2023

We'll start off with an honorable mention. More of a milestone than an actual moment, but it sure felt good in the moment. Win #200.

For all of 2023, it was pretty obvious the big milestone for Adam Wainwright was to notch career win #200. There was some early optimism that he may knock that door down early on and try to chase down Jessie Haines for second all-time at 210, but early season injuries mirrored with struggles brought those expectations back down to earth. In fact, most of the season has been a struggle for Wainwright. A historical struggle. He endured a wallop in the U.K. on an international stage. A beating in Houston, we don't talk about. And, a career-worst 1 inning performance against the lowly Kansas City Royals where he looked, plainly, awful. It was 11 starts between win 198 against the Mets and win #199 against the Orioles in Baltimore. Man did he earn it.

That brought him home at Busch to face the Brewers and get his chance for #200. Wainwright admitted that in his Warm-up, he didn't feel he had his best stuff but that he was going to leave it all out on the line for the chance. Boy did he. As if he owned a time machine Wainwright turned back the clock for this September night and pitched a masterpiece. The only time all season he didn't allow a single run, Wainwright worked wonderfully through 7 strong innings allowing only 4 hits, and got the run support he needed, 1, on a Wilson Contreras solo homerun to earn win #200.

He did it in vintage Wainwright fashion, getting double-play balls and working out of jams. Getting a key strike out here or a clutch fly out there. It was an oasis for the soon-to-be-retired veteran in what has been such a tough season for him, and the Cardinals in 2023. For one last time, Wainwright was the ace and that was a beautiful moment to watch.

Waino's CG SO in front of 2006 World Series alumni - 07/16/2016

2009-2014 was arguably Wainwright's peak. He finished in the top three in Cy Young voting four times, an all-star three times, and accumulated some nasty stats including a 92-50 record, a 2.83 ERA, 1.11 WHIP, and a 3.89 SO/W ratio. He was not only the ace of some very good St. Louis Cardinal teams, he was one of the best pitchers in baseball. So when 2015 came around and Wainwright was dominant once more to start the campaign, it was such a devastating blow when his Achilles ruptured in Milwaukee in late April ending his season with only 4 starts to his name for the year. The future was unknown for the soon-to-be 34-year-old and he knew that he had some work to do to get back to where he was.

That's where 2016 found Waino trying to find that form again early in the year. He was still effective, sure, just not the dominant ace the league was used to seeing. Through April 2016, he accumulated a 7.16 ERA and didn't earn his first win of the season until April 27th. May and June came and went and he saw better numbers with a 4.62 and a 3.69 ERA respectively, still, not the numbers he or others were used to. He had not made it past the 7th inning in any start to this point and only 2 out of the 16 starts had he allowed no runs. Something the uber-competitive Wainwright was known for being stingy about.

So after flirting with dominance the first two starts of July allowing only 1 earned run and striking out 14, on July 16th Waino found that form and reminded us he was still the ace of the staff. The first start out of the all-star break and a weekend celebration of the 10-year anniversary of the 2006 Championship team with friends and alumni in attendance, who else would St. Louis hand the ball to other than the same pitcher that closed out that same World Series 10 years ago?

Navigating 120 pitches against a pretty good Marlins Line-up that included Giancarlo Stanton, Ichiro, Marcell Ozuna, and Christian Yelich, Adam Wainwright with the distance. Through 9 full innings, his final line read 9.0 IP, 0 R, 5 K, 3 H, 2 BB. Sure it wasn't the most dominant Waino has ever been as this was his 10th CG up to this point in his career, but it was a moment. At his home ballpark, in front of former teammates, coaches, and staff, after coming back from a serious injury, and throwing Molina, Waino shoved. Turning back that clock and finding that form again on that hot St. Louis night Adam announced he was back.

#325---September 14th, 2022

When you think of Adam Wainwright the thought of Yadier Molina is synonymous. This one wasn't a pressure-fueled in-game pitch-by-pitch moment. This was a moment that recognized the longevity and greatness of not only Adam Wainwright but Yadier Molina as well. Two franchise icons stayed with the organization collectively throughout the years while others came and went. It became increasingly obvious that there was a connection there between the two that was special, historically special.

It's amazing to think about it in retrospect that in the modern game, two players spent their entire careers beside one another in the same clubhouse for close to two decades. Molina from 2004-2022, and Wainwright from 2005-2023. In this day and age, it's increasingly more common that players will change teams two, three times, and sometimes more. It's also a younger person's sport as well, with more bullpen use being integrated on a game-to-game basis than the conventional workhorse or old-school 20-game winning ace.

Coming into the 2022 season both Yadi and Waino were not even guaranteed this moment either as both were free agents. Wainwright was coming off a stellar '21 campaign in which he went 17-7 with a 3.05 ERA in over 200+ innings, and finished 7th in CY Young voting. He re-signed with St. Louis on a one-year deal for 17.5 Million. Molina, on the other hand, was contemplating retirement and was largely persuaded to come back in an effort to collectively chase the All-Time record for starts as a battery with his friend. He eventually did and announced in spring training that this would be his last season. It made it even sweeter when St. Louis resigned franchise legend Albert Pujols to a one-year deal as well.

The pair started the season 4th all-time in starts together as battery mates at 304, and needing just 20 to tie the all-time record of 324 set all the way back in 1975 by Mickey Lolich and Bill Freehan (gives you an idea of how improbable this record is to be broken again). Through all the ups and downs that final seasons can bring, such as Molina missing close to two months in the middle of the season, Wainwrights sometimes shaky command, or poor end to the season. The stars were always going to align it felt like (pun intended), and they did, on September 14th, 2022. The iconic duo got their collective moment as they exalted themselves into baseball history against the Brewers. Christian Yelich respectfully took strike one down the middle in front of a sold-out Busch Stadium and with a tip of the cap, camera flashes popping, and generations of Cardinal fans looking on, start 325, and the record was theirs.

The Birds went on to win the game 4-1 and continued to press themselves closer to the post-season, but truly Wainwright and Molina were all the talk of the game. With Molina retiring at the end of 2022 the record now stands at 328 starts together. It was truly a testament to longevity and a commitment to excellence that stands out when one thinks of #325.

2006 WS Game 5

The first of two iconic moments that Wainwright himself will tell you, he was just lucky to be a part of. All the way back in 2006, and not even a starter yet, baby-faced 24-year-old Adam Wainwright was thrust into what every ballplayer dreams of. An opportunity to clinch a World Series Championship for his team.

Already taking down the mighty Mets in an epic 7-game series and putting his name and his curveball on the map for all the baseball world to see (more on that in a minute), St. Louis and Adam Wainwright had a date with Detroit, and the star-studded Tigers lineup.

Coming into the series the Tigers had won seven in a row and had a full week of rest before the series started. Also, just like the Mets had home-field advantage. They again were the favorites. That didn't seem to matter much to the Cardinals as they jumped out to a quick 1-0 series lead in a Game 1 rout, 7-2. Detroit, behind Kenny Rogers in Game 2, smeared across three runs, battled back, and evened the series 1-1. After that, the Cardinals took advantage of some shotty Detroit defense and timely hits of their own to secure Games 3 & 4 and the opportunity to head into Game 5 just one win away from a championship.

Game 5 seemed to go pretty much St. Louis way all night as well. Behind the soon-to-be World Series MVP David Eckstein, and 8 brilliant innings by starting pitcher Jeff Weaver, St. Louis went into the ninth with a 4-2 lead. This was Wainwright's moment.

Facing the 4-5-6 hitters, Magglio Ordonez, Sean Casey, and Ivan Rodriguez, Wainwright knew the Tigers were not going to go down easy. Facing the first batter, he worked the count full and got Ordonez to ground out 4-3 to second base for one away. That brought up hard-hitting Sean Casey, already with a 2-run HR on the night, stung a ball into the gap of right-center for a one-out double to bring the tying run to the plate in Ivan Rodriguez. "Pudge" was always a threat at the plate, even here in his twilight years he was someone you didn't want to miss your pitch to. Luckily Wainwright, after missing with two pitches away, was able to execute a pitch inside and got a dribbler back to the mound where he pounced, fielded, and threw out Rodriguez at first for out number two. Former Cardinal Placido Polanco then came to the plate representing the final out for Detroit. The nerves must have been getting to young Wainwright because he not only corked a wild pitch advancing the runner on second to third, he also walked Polanco, bringing up Branden Inge and setting up the winning run for Detroit.

Pitching Coach Dave Duncan then came to the mound to have a talk with his young battery in Wainwright and Molina and talk through how to get out #27. Once he disappeared and returned to the dugout, the determined glare of a concentrated Adam Wainwright needed just three pitches. Strike one an offspeed pitch down and away to a swinging Inge. Strike two a breaking ball that dropped in at the last minute to make it 0-2. Then, with one last big breath before his delivery, the then-rookie Adam Wainwright delivered a third straight off-speed pitch to Branden Inge and for the first time since 1982, St. Louis had a World Series winner.

2006 NLCS Game 7

Hard to believe that what many, myself including, view as the biggest moment of Adam Wainwright's career came all the way back in his statistical rookie year of 2006. NLCS Game 7 against the Mets. Rewind a month prior and St. Louis's All-star closer Jason Isringhausen, had just gone down with season-ending hip surgery. So, on September 17th, with only one career save to his name, 24-year-old Adam Wainwright took over for the Cardinal's all-time saves leader in the midst of a pennant race.

Wainwright notched two more saves in late September to bump his career save total to 3 and helped clinch a wild card birth for a very wild 83-win Cardinals team. With stars like Edmonds, Pujols, Rolen, Carpenter, and a young Molina, Wainwright was talented sure, but more of an afterthought. A future star waiting to bud. That time to bloom was now.

St. Louis entered the post-season with the third-worst record for any MLB playoff team at the time. Yet they continued to have their way with the San Diego Padres in the postseason and eliminated them in the NLDS in 4 games, setting up a David vs. Goliath feel against the heavily favored 97-win New York Mets.

The series was extremely hard fought by both sides and as Game 5 came to an end, the Cardinals actually led 3-2 in the series, but the Mets had home-field advantage and the series was heading back to New York for Games 6 & 7. In Game 6 the Mets came out firing and led off the game with a lead-off HR by Jose Ryes against the Cardinals ace Chris Carpenter and carried that momentum throughout the game to eventually take Game 6 by a score of 4-2. Forcing a win-or-go-home Game 7 in Flushings New York.

Game 7 lived up to the billing with St. Louis starter Jeff Suppan opposite Mets starter Oliver Perez matching each other in a 1-1 ball game all the way to the ninth inning. THIS WAS A NAIL BITTER. Then in the top of the ninth, with 6 HRs on the season, 23-year-old Yadier Molina swatted a deep fly ball to LF that cleared the wall, and Endy Chavez's glove, to give the Cardinals an unprecedented 3-1 lead going into the bottom of the ninth. Enter, Adam Wainwright.

Waino, bracing the cold October air looked towards the plate to face 7-8-9 in the Mets order and send the Cardinals to the World Series. Easy, right? Wrong. Wainwright also had to face the 56,357 screaming Mets fans as well. He allowed back-to-back singles to both Jose Valentin and Endy Chavez to lead off the inning and bring the immediate winning run to the plate in pinch-hitter Cliff Floyd. Sitting 2-2 in the count, Wainwright may have foreshadowed impending doom for the Mets as he dropped a beautiful curveball to catch Floyd looking on strike 3. One out. That then brought perennial all-star Jose Reyes to the plate representing the winning run. Reyes, after taking a curveball for a strike and fouling another off inside, whacked a 1-2 hanger into shallow CF, but that's just where Edmonds loved to play. Shallow. Two outs. Wainwright then missed on a 3-1 fastball outside to Paul Lo Duca and loaded the bases to bring up Cardinal killer, Carlos Beltran.

Wainwright found the weight of the world on his shoulders as he was the man tasked with getting the last out and sending his team to the World Series, or home. He found the sign from Yadi and began the sequence, a change-up, strike-one. A curve ball inside that Beltran got a piece of for strike-two. Now one strike away from securing the save and a mob on the mound, Molina set his signs, tapped the ground, and watched, along with Beltran, and millions around the country, as the the most beautiful curveball fell into his glove for strike three.

By far the most legendary moment of his distinguished career. One that plays over and over again in Cardinals post-season highlights, and I'm sure many fans heads and hearts as well.

There are many other moments that come to mind when I think of the career of Adam Wainwright. We hope you enjoyed this list. What would yours be?