15 worst St. Louis Cardinals' trades in franchise history

These are the 15 worst trades in St. Louis Cardinals history

The St. Louis Cardinals are one of the most storied franchises in all of baseball history, but no matter how much success the club has had, no Major League team is immune to disastrous moves.

A few weeks ago, I took a look at the 15 worst contracts given out in the Cardinals' franchise history. Fortunately, the Cardinals haven't made too many significant missteps in that area. While there are plenty of bad contracts in the club's history, it does not even come close to comparing to some of the bad deals handed out by the free spenders in the sport.

When it comes to bad trades though, things get a lot more painful. When trades go wrong, they not only frustrate you with the player or players the team got in return but they often times mean there was a major success for the club on the other side of the trade. For some reason, it feels much better to waste money on a bad contract for a player than it does to acquire a disappointing player, or worse, give away premier talent.

The Cardinals have famously made some incredible trades that changed the trajectory of the franchise, including their two current cornerstone players, Paul Goldschmidt and Nolan Arenado. But there have also been some plain awful trades for the club, including some in recent memory that the team is still reeling from.

With all of that being said, let's take a look at the 15 worst trades in St. Louis Cardinals' history. Buckle up, as we are going to pick away at some old scabs and fresh wounds here.

#14 - Trading away Coco Crisp

The Cardinals drafted Coco Crisp back in the 1999 MLB Draft, but in an effort to make a run in the playoffs in 2002, they sent Crisp to the Cleveland Indians along with prospect Luis Garcia for starter Chuck Finley.

Finley was pretty good for the Cardinals, going 7-4 with a 3.80 ERA over 14 starts for the club, but they fell short of championship aspirations and Finley retired after that season.

Crisp, on the other hand, would make his MLB debut later that season, and go on to have a very successful 15-year career for the Indians, Red Sox, Royals, and Athletics. including playing a big role on the World Series-winning Boston team in 2007.

During his career, Crisp slashed .265/.327/.402 with 130 HR, 639 RBI, and 309 SB while playing great defense and even finishing top 15 in MVP voting in 2012. While Crisp was never an All-Star level player, he did make a major impact on multiple winning clubs, and surely was worth more than a half-season rental of a middle-of-rotation, at-best, starter.

#13 - Sending former MVP Joe Torre to the Mets

Just a few years after his MVP performance in 1971 and one year removed from being an All-Star, the Cardinals dealt Joe Torre to the New York Mets in October of 1974, acquiring two pitchers, Ray Sadecki and Tommy Moore.

If you don't recognize those two names, I don't blame you. Moore and Sadecki combined to throw all of 19.2 innings for the Cardinals in 1975, with both players having that be their only seasons played for the club.

While Torre did not go on to set the world on fire for the Mets, he did have one more great season in 1976 before retiring following the 1976 season. Torre would then begin his managerial career for the New York Mets in 1977 and would become a Hall of Fame manager, even having some time in the dugout for the Cardinals.

Whenever you consider trading away a club icon, you need to get the deal right, and the Cardinals did not do that here. They got almost nothing in return for Torre and ended what was a great run with St. Louis on an odd note.

#12 - Trading Ken Boyer to the New York Mets

This one may be a little more debatable, but Ken Boyer is another Cardinal legend, who has his number retired by the club and was sent out after his prime in unceremonious fashion.

Boyer won the National League MVP in 1964, and after dropping off during the 1965 season, was sent to the Mets in exchange for third baseman Charley Smith and pitcher Al Jackson. Smith was fine at third base for the Cardinals in his only season with the club, while Jackson was incredible in his first year with the club.

Despite going 13-15, Jackson put up a 2.51 ERA in 232.2 innings of work for St. Louis in 1966, and after faltering some the season after, made his return to the Mets in 1968.

While Boyer only had two well-above-average seasons over the last four years of his career, parting with a legend like that is a tough pill to swallow. Jackson's performance makes this trade not a complete fail, but I'm sure they'd like to have ended on a better note with their Red Jacket club member.

#11 - The Luke Gregerson for Khalil Green trade

For much of the 2000s and 2010s, it felt like the Cardinals could never land on a long-term answer at shortstop. With this being one of the most important positions in baseball, it makes sense why St. Louis took so many swings at the position. Trading for former esteemed prospect Khalil Green was a big swing, and it turned out poorly for the club.

Greene only played in 77 games for St. Louis before severe anxiety forced him out of baseball entirely. We know a lot more about the importance of mental health in today's world, but his struggles were not something widely talked about back in 2009. This set the Cardinals back at shortstop once again.

On top of that, St. Louis gave up one of the most reliable relievers of the 2010s, Luke Gregerson, in a package that also included Mark Worrell.

Gregerson went on to pitch eight seasons before returning to St. Louis, posting a 3.02 ERA in 599 innings for the Padres, Athletics, and Astros. That kind of production over an eight-year period from a reliever is pretty rare, and the Cardinals missed out on that production dearly. In his return to St. Louis, Gregerson only threw 18.1 innings with a 7.36 ERA.

#10 - Scott Rolen for Troy Glaus

Starting off the top 10 with some more controversy, a very disgruntled Scott Rolen was sent to the Toronto Blue Jays for slugger Troy Glaus before the 2008 season. If this article was written after that season, the trade would have been a huge steal for St. Louis. But in the years following, it has not aged well.

Rolen was seemingly declining offensively in a big way and was frustrated with manager Tony La Russa, so swapping him for a guy who would slash .270/.372/.483 with 27 HR and 99 RBI was incredible in the moment. But in 2009, Glaus would only play in 29 games for St. Louis, and then was done with his Cardinal career.

Rolen on the other hand, played an additional five seasons, earning two more All-Star appearances, a Gold Glove, and finishing top-15 in MVP voting for the Reds in 2010. The short-term gains of Glaus were not worth the long-term loss of a future MLB Hall of Famer.

#9 - The Randy Arozarena trade

This trade happened back in January 2020, and at the time, received a lot of mixed reviews. Some applauded the Cardinals for grabbing a high-level pitching prospect like Matthew Liberatore, while others didn't like the idea of giving up a proven bat in Jose Martinez and a promising outfielder in Randy Arozarena. To this point, the Rays look like they won the deal in a robbery.

Arozarena would set the post-season home run record in 2020 for the Rays, hitting 10 bombs on their way to the World Series that year. The following season, Arozarena would post a 129 wRC+ and win rookie of the year, followed by a 124 wRC+ season in 2022. While the Cardinals have plenty of quality outfield options now, he would have been a great piece for them in 2020 or 2021, and even if they did end up dealing him, could have netted them a lot more in return.

The Cardinals did receive catcher Edgardo Rodriquez as well, but the centerpiece for them was the lefty Liberatore. Liberatore has still yet to establish himself as a quality big-league arm, posting a 5.97 ERA in 9 games during his rookie year last season. There is still time for him to turn this around, but it's hard to imagine him being good enough to make this trade even defensible for St. Louis.

The Cardinals traded away a young impact back with great defensive ability in Arozarena, and that's something John Mozeliak and company must regret often.

#8 - Adolis Garcia to the Rangers for cash

Any time a player is shipped away for cash, I feel like it's a high-risk, low-reward scenario. Oftentimes, the cash is minuscule at best and rarely factors into future moves or decision making. Often, these deals end up being forgettable for both teams, but in the case of Adolis Garcia to the Texas Rangers, the Cardinals have to be shaking their heads at themselves.

Garcia barely made an impact in the 21 games he played for St. Louis in 2018, posting a .294 OPS in his 17 at-bats. I know St. Louis had a logjam in the outfield, but sending away someone with the tools that Garcia had for just cash, especially after being a productive Minor Leaguer, seems like a bad move even without the hindsight we have now.

In 2021, Garcia was an American League All-Star for the Rangers and finished 4th in Rookie of the Year voting. Last year, Garcia slashed .250/.300/.456 with 27 HR, 101 RBI, and 25 SB while playing in 156 games. While Garcia isn't a sure bet over the Cardinals' other outfield options, it's safe to say the club could've at least gotten a lot more value for the outfielder.

#7 - Acquiring the injury-prone Mark Mulder for a multi-time All-Star

It's hard to fault a team for "going for it" when they see their championship window. In 2005, the Cardinals' acquired a young star in Mark Mulder, who finished 2nd in Cy Young voting in 2001 and was an All-Star in 2003 and 2004.

Unfortuantely for St. Louis, Mulder had already peaked.

After going 16-8 with a 3.64 ERA in 2005, Mulder would struggle with injuries and terrible performance before his big league career would end in 2008. Mulder's career took a downturn that few could've predicted, but what hurts even more are the assets they gave up to get him.

Outside of giving up two useful players in the forms of Daric Barton and Kiko Calero, Dan Haren would emerge from a so-so young starter with the Cardinals into a three-time All-Star, two-time top 7 finisher in Cy Young voting player over his 13 big league seasons. The success for Haren came pretty quickly, as he was a very similar pitcher to Mulder in 2005 and earned his first All-Star appearance in 2007.

#6 - Trading away Jerry Reuss

Jerry Reuss pitched in 57 games for the Cardinals during his age 20-22 seasons, amassing a 22-22 record with a 4.43 ERA in 345.1 innings pitched. Trading him away would not have shocked anyone, but trading him turned out to be a big mistake.

Reuss ended up pitching for 22 years in the league, posting a 220-191 record with a 3.64 ERA in 3669.2 innings for the Dodgers, Pirates, Astros, White Sox, Angels, Reds, and Brewers, along with his debut team, the Cardinals.

Not only was trading away that kind of longevity a mistake, but he also had two All-Star seasons mixed in there, including top 20 MVP finishes twice and second in Cy Young voting in 1980.

#4 - Trading Reggie Smith to the Dodgers

Trading away a future World Series winning, middle of the order bat who would also go on to win a Gold Glove? Yikes.

Reggie Smith was really good for St. Louis during his three-year stretch, posing a .293/.371/.495 slash line with 50 HR and 199 RBI, but those numbers were dipping during the 1976 season. In came the Dodgers, who gave them a few players that would do relatively nothing for St. Louis.

Smith, on the other hand, would be a 145 wRC+ hitter the final seven seasons of his career, becoming a star in Los Angeles. He went to three All-Star Games during that time, and finished top-4 in MVP voting in 1977 and 1978.

Hard the Cardinals stuck it out with Smtih, he may have become a club legend. Instead, he made noise with the Dodgers and the rest is history.

#4 - Cardinals send three stars to Milwaukee

By names alone, this trade could be even higher on the list. The only saving grace for St. Louis in this awful deal is that each of the players had relatively short careers following the trade.

After acquiring Bruce Sutter from the Cubs, the Cardinals sent Rollie Fingers, Ted Simmons, and Pete Vuckovich to the Brewers for David Green, Dave LaPoint, Sixto Lezcano, and Lary Sorensen. All four of those players ended up being decent players for St. Louis, but each of the players they sent out continued to play at a high level.

Fingers was acquired that same offseason by St. Louis and dealt to the Brewers just days later, and ended up having a 1.04 ERA and 28 saves in route to the Cy Young and MVP in 1981. He'd become an All-Star again in 1982 and then only pitch two more seasons following that.

Ted Simmons was a Hall of Fame catcher and produced two more All-Star quality seasons himself following the trade, though outside of that, he was not much more than just a good catcher for the other six seasons he played. after the trade.

Vuckovich followed up Fingers' Cy Young with his own in 1982, but also only pitched three more seasons following that. All in all, St. Louis gave up two future Cy Young award winners and a two-time All-Star catcher in this deal, while only getting servicable players back.

I can totally see this trade deserving a higher ranking on the list, but unfortunately, we've entered some territory where all of these trades will look really bad.

#3 - The Marcell Ozuna Trade

The Cardinals needed a big bat prior to the 2018 season, and Marcell Ozuna was coming off of a .924 OPS season along with a Gold Glove for the Miami Marlins. After striking out on the Giancarlo Stanton trade, St. Louis acquired Ozuna from the Marlins for a package of prospects headlined by two of their lower-ranked pitching prospects, Sandy Alcantara and Zac Gallen.

Yeah, that went about as bad as it sounds.

Ozuna was pretty good for St. Louis over his two seasons there, posting a .777 OPS across 278 games played, but was allowed to leave in free agency following the 2018 season.

On the other side of this trade, Alcantara is coming off a 14-9 season where his ERA was 2.28 over an MLB-high 228.2 innings pitched and a Cy Young award at age-26. Alcantara is easily one of the best pitchers in all of baseball, in his prime, and on an extremely team-friendly extension for the foreseeable future.

Gallen was a Cy Young candidate himself this last season for the Arizona Diamondbacks. He went 12-4 with a 2.54 ERA over 184 innings of work and has also emerged as a top stater in today's game. Also entering his age-27 season, the Cardinals effectively gave up two young, in their prime aces for a two-year rental of Ozuna.

Ouch.

What really hurts is that if the Cardinals' had these two guys, they are easily the World Series favorites this year. Even with just one of them, they likely are neck and neck with the best teams in the league, and still would have so many assets to deal if they desired. You can check out a deeper breakdown of the Ozuna trade here.

#2 - Keith Hernandez to the Mets

There was a lot that played into the trading of Keith Hernandez that had little to do with his on-the-field play, but regardless, the rest of his career made St. Louis look foolish for giving up on him.

During his 10 years with the Cardinals, Hernandez slashed .299/.385/.448 with 81 HR and 595 RBI while winning an MVP in 1979 and six Gold Gloves for the club. Trading away a terrific hitter and one of the best defensive first basemen ever in his prime aged about as well as you would think.

Hernandez would finish 2nd in MVP voting in 1984 and top-8 two other times after leaving the Cardinals, while also being awarded five more Gold Gloves, three All-Star appearances, and one Silver Slugger during his Mets career.

It has to pain Cardinals fans to think about what could have been in Hernandez was able to stay in St. Louis. Unfortunately, he got to put together a heck of a second half of his career with the Mets. If the Cardinals can learn anything from this list, it's to stop trading proven talent to the Mets.

#1 - Steve Carlton to the Phillies

This one just dumbfounds me, even more so than the other deals on this list.

Future Hall of Famer, Steve Carlton, was coming off his age-26 season with St. Louis, whom he'd been a three-time All-Star with already and amassed a 77-62 record with a 3.10 ERA in 1265.1 innings. The Cardinals had a young ace on their hands, but the Cardinals refused to pay him the $65,000 salary he was asking for and instead traded him to the Phillies.

How'd Carlton respond to that deal? The next season, he went 27-10 with a 1.97 ERA in 346.1 innings of work while winning the Cy Young and finishing 5th in MVP voting.

Carlton went on to win three more Cy Youngs after that, finish top-4 two more times, top 15 in MVP voting five more times, and become an All-Star six other times as well. All in all, Carlton went 241-161 with a 3.09 ERA in 3697.1 innings of work for the Phillies during his 15 years there.

Letting money get in the way of paying a Hall of Fame-level pitcher about to begin his prime is about as ridiculous as penny-pinching can get. Carlton is one of the best pitchers of all time and should be known as that in a Cardinal uniform. Instead, they dealt him for practically nothing and watched him shut down opponents for another 20 seasons.