St. Louis Cardinals: Ranking the 10 worst trades in the last 20 years

The St. Louis Cardinals have made some great trades over the past 20 years, but there have been a few duds along the way.

Lou Brock for Ernie Broglio is almost undoubtedly the greatest trade in St. Louis Cardinals history. But then we have those trades that Cardinals fans would probably prefer to forget. The trade of Steve Carlton to the Philadelphia Phillies for Rick Wise is likely the most regrettable.

A 2017 article from Christian May-Suzuki detailed the best trades the Cardinals made from 1997 to 2017. But now it’s time to take a darker path and look at the ones that didn’t work out so well.

This list was compiled by looking at the value of the players received and dealt and how they affected their teams after the trades. It also looks at how the Cardinals could have fared if the player were still on the team.

Some of these trades are quite recent, so a full judgment of how they affected the Cardinals remains to be seen. But because we are only going back 20 years and the Cardinals haven’t made many bad trades, the options are limited.

Here are 10 deals Cardinals general managers made that they might wish they could take back.

10. St. Louis Cardinals trade Marc Rzepczynski for minor leaguer.

Cardinals Receive: Juan Herrera

Indians Receive: Marc Rzepczynski

Rzepczynski came to the St. Louis Cardinals in the 2011 mega-trade with the Toronto Blue Jays that also netted the Cardinals Octavio Dotel, Edwin Jackson and Corey Patterson. The 2013 Cardinals bullpen had some solid left-handers, so Rzepczynski’s trade was understandable.

He performed pretty well for the Cardinals in 2011, but he began to struggle in 2012 with a 4.24 ERA, and his troubles heightened during his brief time in the majors in 2013. He was shipped off to Cleveland in July, where he turned things around.

Rzepczynski’s time from 2013 on was decent for the most part. He pitched to an ERA of 3.72, including 0.89 in his 20.1 innings with Cleveland in 2013. The change of scenery seemed to do him some good. He has amassed a respectable 198 strikeouts in 201 innings since 2013 as well. Since Rzepczynski left, the Cardinals have had some trouble with left-handers in the bullpen (see Cecil, Brett).

The player the Cardinals received, Herrera, never really materialized. He struggled to hit in High-A and Double-A after the trade, and he was last seen in independent ball in 2017. While this trade will never be seen as a disaster, Rzepczynski could have solidified the bullpen in later years.

9. St. Louis Cardinals acquire two bullpen arms for Luke Voit.

Cardinals Receive: Chasen Shreve, Giovanny Gallegos

Yankees Receive: Luke Voit

In the St. Louis Cardinals’ seemingly endless search for left-handed bullpen arms, the team decided to part ways with Voit to get Shreve and prospect Gallegos. After the trade, Voit received ample playing time and absolutely mashed, hitting .333 with 14 homers in 132 at-bats with the Yankees.

This power stroke never really materialized in his Cardinals tenure, where he only hit five home runs in 125 at-bats. He’s started slowly for the Yankees this year, but he’s shown some signs of turning it around lately.

Voit likely wouldn’t have had much of a chance to play regularly for the Cardinals, barring injuries, so the trade made sense. Matt Carpenter was playing first base, and Voit’s main role was as a pinch-hitter. Swapping him for pitching was a logical move.

Unfortunately for the Cardinals, Shreve failed to impress. He struggled with control, walking nine batters in 14.2 innings. He also surrendered five home runs. Shreve was designated for assignment on March 22, but he went unclaimed, so the Cardinals sent him to Memphis on March 27.

Gallegos continues to show promise, however. His last extended stretch was in Triple-A in 2018 where he pitched to a 2.64 ERA with 57 strikeouts in 44.1 innings. His big-league exposure has been limited, but his strikeout rate is quite high with the Cardinals. He could become a good bullpen piece as he gets more time in the MLB.

While it’s too early to call this trade a true loss for the Cardinals, Voit has served as a game-changer for the Yankees, while Shreve hasn’t done much to warrant staying. Gallegos, though, still has a chance to make the trade worth it.

8. St. Louis Cardinals ship out Jack Wilson.

Cardinals Receive: Jason Christiansen

Pirates Receive: Jack Wilson

The St. Louis Cardinals drafted shortstop Jack Wilson in the ninth round of the 1998 draft, but they traded him to the Pittsburgh Pirates for relief help in Christiansen. Later that year, the team traded for Edgar Renteria, which has gone down as a great trade for the Cardinals.

Renteria held down the fort from 1999 to 2004, his last year being Wilson’s lone All-Star appearance. Needless to say, shortstop was solidified for the team, and when Renteria left, David Eckstein filled the void.

Wilson batted .265 and played decent defense at shortstop throughout his career. In 2004, Wilson led the National League in assists, putouts and total chances, and he played 31 consecutive games without committing an error.

Wilson likely would have been the odd man out in the infield had he stayed, but if the Cardinals held on to him for a bit longer, he might have been able to be traded at a higher value and net someone better than Christiansen, who only pitched 29.1 innings with the Cardinals and had an ERA of 4.91. Christiansen was traded to the San Francisco Giants a year later for Kevin Joseph and cash.

Whenever a player who has yet to make his debut is traded and has a long, solid career, and the player received is a short-term solution and isn’t even that good with that team, it’s hard to chalk up the trade as anything but a failure, even if Wilson wasn’t going to fit into the Cardinals’ long-term plans.

7. St. Louis Cardinals deal Tommy Pham for three prospects.

Cardinals Receive: Genesis Cabrera, Roel Ramirez, Justin Williams

Rays Receive: Tommy Pham

The late-blooming Pham was outstanding with the St. Louis Cardinals in 2017, hitting .306 with 23 home runs in 444 at-bats. At the deadline of a less impressive 2018, where his batting average sat at .248, he was dealt to the Rays for Cabrera, Ramirez and Williams. Pham was having some disagreements with the organization and Mike Matheny, so the fresh start could have done Pham some good.

Indeed, Pham was a monster with the Rays after the deadline, hitting .343 in 143 at-bats. He hasn’t slowed down this year, as he is still putting up great numbers for the Rays. Pham could have been a starter in the outfield for the Cardinals this year, although the team has made up for his absence.

Williams hit .252 with 11 home runs in 425 at-bats between the Rays’ and Cardinals’ Triple-A clubs. He’s been on the injured list since the start of the season with a finger injury, and he has a total of one plate appearance in the major leagues.

Ramirez has gotten off to a poor start with Double-A Springfield, pitching 10.2 innings so far and giving up 13 hits and 10 earned runs. He gave up six earned runs in 10.2 innings in Springfield last year after the trade to the Cardinals, so things aren’t looking good for him.

Cabrera has also struggled since coming to the Cardinals. He had a 4.74 ERA in Springfield last year and surrendered 13 earned runs in 24.2 innings. He was promoted to Memphis to begin 2019 and has so far fared worse, giving up 16 hits, 14 earned runs and six home runs in only 12.1 innings.

This trade could still be salvaged if Ramirez and Cabrera turn things around. We still need to see more of Williams to know what he possesses, but for now, it looks as if it could be a heist for the Rays.

6. St. Louis Cardinals give up two prospects for Chuck Finley.

Cardinals Receive: Chuck Finley

Indians Receive: Coco Crisp, Luis Garcia

The St. Louis Cardinals drafted Crisp in the seventh round of the 1999 draft, and he made his major league debut for the Cleveland Indians eight days after the trade. Crisp went on to have a solid career, especially in the basestealing department, swiping 309 bags in his career, including leading the American League with 49 in 2011.

More from St Louis Cardinals History

• Reflecting on the 2013 Cardinals’ top 30 prospects
• Cardinals: The best Silver Slugger performances at each position.
• The St. Louis Cardinals are in rare company with this free agency stat
• What Happened to the 2011 St. Louis Cardinals? Matt Holliday Edition
• The St. Louis Cardinals avoided disaster with Jason Heyward

The Cardinals wanted an effective arm in their hunt for a championship in 2002, so they made the trade, sending Crisp and minor leaguer Garcia to the Indians for established reliever Finley.

Finley, for his part, did well with the Cardinals in what would be his last year. He had a 3.80 ERA in 85.1 innings and only gave up 69 hits and 30 walks. Unfortunately, he couldn’t help the Cardinals to a title.

Crisp might have fit into the Cardinals’ plans in the outfield, especially right field, which was a revolving door after the trade of J.D. Drew. Reggie Sanders, Larry Walker and Juan Encarnacion all held the position in the three years following it. Crisp also could have provided the Cardinals with some speed, which would have been beneficial in years like 2007, where the stolen-base leader, David Eckstein, only had 10.

There isn’t much to say about Garcia. He hit .266 with the Cardinals’ Double-A affiliate, then played in the Dodgers’ and Mets’ farm systems. He spent the rest of his career playing in Mexico and Japan, finally calling it quits in 2018 at age 39.

The trade of Crisp made the Cardinals lose a good speed threat, although as the team often does, it filled the position pretty well. Still, it would have been nice to see Crisp tearing up the bases on a mostly station-to-station team.

5. St. Louis Cardinals, Miami Marlins swap relievers.

Cardinals Receive: Steve Cishek

Marlins Receive: Kyle Barraclough

In a swap of relievers, the St. Louis Cardinals were looking for immediate bullpen help and gave up a mostly unknown minor leaguer in Barraclough in exchange for the sidewinder Cishek.

Cishek wasn’t terrible with the Cardinals in his brief time with the club. He had a 2.31 ERA in 23.1 innings and struck out 20 batters. He did walk 13, but it was a decent rebound from his struggles with Miami earlier that year. The Cardinals released Cishek after the season, and he signed with the Seattle Mariners. The sidearmer has bounced around since then, but he’s put up solid numbers.

Barraclough, though, was better than almost anybody expected with the Marlins. He was called up to Miami a few days after the trade, and he pitched very well. He had an ERA of 2.59 in 24.1 innings and struck out 30 batters. In 2016, Barraclough struck out an outstanding 113 batters in 72.2 innings while also cutting his walk rate.

His 2017 was strong as well, although he took a step back in 2018. Barraclough signed with the Washington Nationals in 2019, and he has had some more trouble with walks.

Although Cishek was far from a disaster with the Cardinals, if a team has talent on the farm, it’s generally better to go with them than look outside the organization. The Cardinals had a very good reliever in their farm system, but they got rid of him for a short-term solution. It’s hard to call that a good deal.

3. St. Louis Cardinals trade pitching for veteran infielder.

Cardinals Receive: Mark DeRosa

Indians Receive: Chris Pérez, Jess Todd

In the middle of 2009, the St. Louis Cardinals traded relievers Perez and Todd for a known commodity in DeRosa. Unfortunately for the Cardinals, DeRosa hurt his wrist just a few games after being traded, and after coming off the disabled list, he couldn’t get going. He hit only .228 with the Cardinals in 237 at-bats after hitting .270 with the Indians earlier in the season. He had surgery after the season and was released.

Pérez was decent in his stint with the Cardinals. He had an ERA of 3.46 in 2008, and the next year, he struck out 30 batters in 23.2 innings before he was traded. 2010 was when Pérez really got going. He became the Indians’ closer and had a 1.71 ERA. He remained the closer for the team through 2013, and he made the All-Star team in 2011 and 2012.

Pérez fell from grace quite quickly, though. He was arrested in 2013 for possession of marijuana and was later released by the Indians. The Los Angeles Dodgers scooped him up in what would be his final major league season. He had an ERA of 4.27 and was released in October. He signed with the Brewers, but he only pitched 7.2 innings in the team’s Triple-A affiliate and gave up 14 runs. He was out of baseball after that.

Todd only had 1.2 major league innings under his belt when he went to Cleveland as the player to be named later. He never found much success in the major leagues, with a career ERA of 7.62 in 28.1 innings. The Cardinals got him back off waivers from the New York Yankees in 2011, but he never saw the majors again.

The Cardinals were going through closer after closer during Pérez’s time solidifying the back of the bullpen with Cleveland. Ryan Franklin, Fernando Salas, Edward Mujica and Trevor Rosenthal all served in the role to varying degrees of success. Some stability might have been appreciated at that time. Even if DeRosa had stayed healthy, it’s hard to think that he would have outperformed Pérez.

2. St. Louis Cardinals trade for former first-rounder Khalil Greene.

Cardinals Receive: Khalil Greene

Padres Receive: Mark Worrell, Luke Gregerson

In 2009, the Cardinals were searching for a long-term answer at shortstop, and Greene looked to be a good solution. He had some decent power, although his career average before arriving was an unimpressive .248.

Unfortunately, Greene struggled with social anxiety and had to take time off during the season. When he was playing, it was clear he wasn’t right. In 170 at-bats, he hit only .200 with six home runs. Most of the starts at shortstop that year ended up going to Brendan Ryan.

In another deal where the St. Louis Cardinals gave up a potential future closer, this one stung even more because Gregerson had more staying power than Pérez did. Gregerson became an excellent reliever for the San Diego Padres, as well as with the Oakland Athletics and the Houston Astros.

Before he returned to the Cardinals in 2018, Gregerson had a 3.04 career ERA with 607 strikeouts in 599 innings. He also earned 66 saves with the three teams and served as the Padres’ primary closer in 2015 and 2016.

Worrell, the main piece in the trade, had good minor league stats but never put it together in the bigs. He pitched 5.2 innings with the Cardinals in 2008 and gave up five runs. He spent three years in the minor leagues, then pitched two innings with the Baltimore Orioles in 2011 and gave up eight runs.

Greene’s troubles with social anxiety were exposed with the Cardinals, as he seemed to keep them pretty well under wraps in San Diego. It was an unfortunate deal, as Gregerson could have been an even better option than Pérez to finish games for the Cardinals.

1. St. Louis Cardinals acquire Mark Mulder for three players.

Cardinals Receive: Mark Mulder

Athletics Receive: Daric Barton, Kiko Calero, Dan Haren

The St. Louis Cardinals were going for it all in 2005, so they flipped Barton, Calero and Haren for Mulder, who, while coming off a down season by his standards, was still expected to produce. And in his first season with the Cardinals, he did, pitching to a 3.64 ERA in 205 innings in 2005. He also pitched well in the postseason that year, but he couldn’t lead the team to a title.

Mulder couldn’t stay healthy for the rest of his time with the team as his shoulder wouldn’t cooperate. He had two rotator cuff surgeries throughout his Cardinals tenure. When he did pitch, he was ineffective.

Over the next three years, Mulder only pitched a total of 106 innings, giving up 150 hits and 96 runs, with an ERA of 7.73. He made one appearance in 2008, leaving the game in the first inning after again hurting his shoulder when attempting a pickoff. He never appeared in another game.

Haren wasn’t spectacular with St. Louis in his first two years in the major leagues, pitching to a 4.85 ERA in 118.2 innings. But he broke out after the trade and became an elite pitcher. He earned three All-Star berths, from 2007 to 2009, and had a 3.70 ERA for his career after the trade, including a sparkling 3.07 in 2007.

The first-rounder Barton was the centerpiece of the trade, but his eight-year career was less than impressive. His outlier was 2010, where he hit .273 and led the American League with 110 walks. He never developed the power teams desire from a first baseman; his 10 home runs in 2010 were a career high.

Calero did pretty well with the Cardinals during his time with the team. He had a 2.80 ERA with 98 strikeouts in 83.2 innings. He faltered a bit during his tenure in Oakland, pitching to a 3.96 ERA. His best season was probably his final one, where he pitched with the Florida Marlins, where he had an ERA of 1.95 and struck out 69 in 60 innings.

The only saving grace for this trade was that the Cardinals won the World Series in 2006. But Haren definitely would have had a spot in a merely adequate rotation during the following years. With the starkly different performances of the player received and who became the best player traded (Haren), this can be argued to have been the worst trade the Cardinals made in the last two decades.

So there it is. If you look back a few more years into Cardinal history you may find worse trades but from 1999-now, that is my take on the list of players the Cardinals should’ve decided to hold on to instead of ship off to another team.