St. Louis Cardinals: Top Ten Free Agent Signings

Top Ten Free Agent Signings in St. Louis Cardinals’ History

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As a fan of the St. Louis Cardinals, there is so much rich history that I remember and also grew up hearing about on the radio or through my father. With free agency starting today, I wanted to examine the history of this club and free agency. Obviously, we all know that it was the Cardinals’ Curt Flood who in 1969 started the movement for what became free agency in 1975.

But, who are the best free agent signings in Cardinals’ history? This took quite a bit of research and time recounting the history of the club. For brevity and time reasons, this will be free agents that came from outside the organization as major league players as free agents, so not including amateur/international free agents. I will be doing this in a quasi historical order, so don’t attack me if I list your favorite free agent last. Let’s get started!

Next: Bob Tewksbury

#1 Bob Tewksbury

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Bob, was signed in the winter after the 1988 season. When Bob was signed the team was coming off of a year in which they finished with a record of 76-86 (5th in the NL East) under manager Whitey Herzog, this a year after losing the World Series to the Minnesota Twins. Tewksbury had previously been with the Cubs and Yankees in his career, having only one good season (injury riddled 87-88) when he went 9-5 with a 3.31 ERA in 20 starts and three appearances out of the bullpen, as a rookie in 1986.

In Tewksbury’s first season as a Cardinal he struggled with injuries again, only appearing in seven games (four starts) in 1989 and totaling an ERA of 3.30. The next season Tewksbury finally put a full season, appearing in 28 games with 20 of them being starts. He finished that year with good numbers, despite his 10-9 record he had an ERA of 3.47 (3.12 FIP), and a WHIP of 1.142.

This started a stretch of four seasons in which Tewksbury was a really good member of the rotation. His best year came two years later in 1992, when he finished the year with a record of 16-5 with a 2.16 ERA (3.12 FIP), 1.017 WHIP, and an average of 0.8 walks per nine innings. This was Tewksbury’s only all star season and was a year in which he finished third in CY Young voting.

Tewksbury went on to spend two more seasons with the Cards before leaving after the 1994 season to finish his career with the Rangers, Padres, and Twins, before hanging it up after the 1998 season.

Tewksbury’s overall numbers for the Cardinals? 67-48 with a 3.48 ERA, which is pretty good for the Cardinals’ first real significant free agent contribution.

Next: Tom Henke

#2 Tom Henke

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After 13 good seasons out of the bullpen for the Blue Jays and Texas Rangers and earning the nickname “The Terminator”, Henke was a free agent after the 1994 season, and the Cardinals got him to come to town on a one year $2,325,000 deal. Henke responded with a monster year as the Cardinals’ closer. Henke finished the season with a 1.82 ERA (career best) and 36 saves for the 62-81 Cardinals.

Unfortunately, Henke was uninterested in another season with the club and decided to hang it up after that season. It would have been interesting to see what Tony Larussa would have done with such a weapon in the bullpen, could have been a key part of that 96 team that lost to the Braves in the NLCS. If you’re interested in why Henke retired after the 1995 season, check out this article from Cooperstowners in Canada.

Next: Delino DeShields

#3 Delino DeShields 

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There are times that I wish I paid more attention as a kid when I watched baseball games, and this is one of them. DeShields was signed after the 1996 season to come in and replace Luis Alicea at second base. DeShields was probably a very exciting player to watch, much in the way that Vince Coleman and Lou Brock were exciting to watch in the 80s.

In Deshields’ first season as a Cardinal the speedy second baseman hit .295 and got on base at a .357 rate. He stole 55 bases that season and was caught stealing only 14 times in 69 attempts. He also contributed 51 extra-base hits that season (26 doubles, 14 triples, 11 homers), those 14 triples were the best in his career and best in the league that season.

DeShields didn’t have as good of a season in 1998 as he did in 1997, but he did have another solid season for the Cards. He finished with .290 average and a higher OBP of .371, but only managed to steal 26 bases in 36 attempts that year. The drop in stolen bases were due to missing over a month in the middle of the season. Which, I gotta figure hurt the team in their hunt for the division title as they finished third that season, despite the wonderful season by Mark McGwire.

DeShields’ son Delino DeShileds’ Jr. is currently playing for the Texas Rangers.

Next: Jason Isringhausen

#4 Jason Isringhausen 

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Who didn’t love Izzy? He burned our hearts with heartburn inducing saves that made us all nervously fret the 9th inning, he nailed down the 9th inning like it was between him and a world series every year. He was without a doubt one of the greatest closers in Cardinals’ history.

Izzy was brought in during the 2001 offseason and was installed as the closer of Tony Larussa’s bullpen right away. In his first season as a Cardinal in 2002, Isringhausen saved 33 games in 40 save situation appearances and was credited with a 3-2 record and while earning a 2.48 ERA which could have been even lower had a little more luck went his way as he had a 1.75 FIP.

Over the course of his seven year career with the Cardinals, Isringhausen accumulated 217 saves (most in team history), a 2.98 ERA, and a FIP of 3.59. A very fine career from one of the game’s best closers. Although, unfortunately an injured hip in 2006 prevented Rosenthal (and paved the way for Adam Wainwright to etch his name in history) from participating in the Cardinals’ only World Series championship during his time in St. Louis. His lead as all time saves leader for the Cardinals will be in jeopardy soon, as Trevor Rosenthal already has 96 saves in just two full seasons as the closer and 3 saves in 2013.

Next: Reggie Sanders

#5 Reggie Sanders

Oct 9, 2015; St. Louis, MO, USA; Reggie Sanders throws out the first pitch before game one of the NLDS between the Chicago Cubs and the St. Louis Cardinals at Busch Stadium. Mandatory Credit: Jeff Curry-USA TODAY Sports

I almost didn’t include Reggie on this list. He did only play two season in St. Louis, but was a large part of those two teams’ in 2004 and 2005. He was brought in during the 2003 offseason to play RF/LF, and was on his seventh team in seven years. In his first season, (which was the only full season he played) he finished the year with a slash of .260/.315/.482 with 52 extra-base hits (27 doubles, 22 homers, and 3 triples) and 67 RBI.

Playing in only 93 games the next season Sanders upped his game a bit, going .271/.340/.546 with a very good OPS of .887, finishing with one less homer than the season before (21) in over 150 less at-bats.

These aren’t jump off the page MVP numbers, but that’s not what was needed out of him on a team as loaded as the 04-05 teams were. He was hitting in a lineup with Albert Pujols, Jim Edmonds, Scott Rolen, and Larry Walker (2004). He didn’t need to be that MVP guy, as the team had the MV3 (still perplexes me how this team didn’t win the title).

Sanders also had pretty good postseason numbers with the Cardinals as he did contribute two very good NLDS performances in 04/05, going .286 with a homer and a stolen base in 04 and .333 with a homer, two doubles, and ten RBI in the 05 NLDS against the Padres. It was the 04 WS and 05 NLCS where his bat went to die unfortunately when the Cards needed it most.

All in all, one of the better signings in Cardinals’ history.

Next: Chris Carpenter

#6 Chris Carpenter 

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In all likelihood this was the best. Carpenter thrived in St. Louis after having so much promise throughout his career in Toronto. Carpenter, was a Dave Duncan project that was signed in the offseason of 2002, who didn’t appear in a single game in 2003 due to injury. Carpenter then was put into the rotation in the 2004 season and he responded by having a career year going 15-5 with a 3.45 ERA (3.85 FIP), unfortunately it was the injury bug that bit him again in 2004 that kept him from the playoffs and likely was part of the reason the Cards lost in the WS that year.

Carpenter followed that year up with an even better year the next, posting yet another career year going 21-5 with a 2.83 ERA (2.90 FIP). This season he was healthy enough to pitch in the postseason and he performed admirably, in three starts he only allowed five earned runs and struck out 12. He was rewarded with the Cy Young that year.

Again, in true Chris Carpenter fashion, he had yet another successful season. It wasn’t quite as good as his 05 regular season, but still really good. He finished a ho-hum 15-8 with a 3.09 ERA (3.44 FIP), and another trip to postseason. Carpenter made mincemeat of the Padres in two starts allowing just 3 earned runs in two starts in that series.

Carpenter, however struggled in his first start against the Mets, giving up five runs and getting bailed out by the offense in the 2nd game of the series. Carpenter would shoulder the loss in Game 6 despite only giving up two runs in the six innings he pitched.

When the team advanced on to the World Series, Carpenter shined in Game 3 going eight scoreless and not allowing a single run on just three hits. Unfortunately, 2007-2008 were years mostly lost to injury.

In 2009, clutch Chris Carpenter was back and he finished the season with another career low ERA of 2.24 (this one would stick) which led the league led his team to a first round playoff series against the Dodgers where Carpenter proved his humanity by giving up four runs in five innings in his only appearance in the series. Somehow, Carpenter finished second in Cy Young voting that year to Tim Lincecum, despite having a better ERA, ERA+, and W-L record.

Carpenter had another great year in 2010 (16-9 3.22) and was an all-star. Unfortunately, this wasn’t good enough to get the Cardinals into the playoffs. However, in 2011 Carpenter posted another solid season (11-9 3.45 ERA) and fired his team up to fight the last month and a half of the season to make the playoffs. We all know the story, so I will spare the details.

Once the Cards got in the playoffs Carp put them on his back, as despite a rough outing in Game 2 of the NLDS, Carp outdueled good friend Roy Halladay in Game 5 pitching a complete game shutout and moving the Cardinals’ on to an NLCS date with the Milwaukee Brewers, where Carpenter was 1-0 in his only start only giving up three runs in his five innings of work, helping the Cardinals win the series and move on to the World Series for the second time in his career.

Carpenter pitched in three games that series, limiting the Rangers to two runs in on six innings in Game 1, two runs on seven innings in Game 5, and coming back on three days rest to pitch six innings, allowing two runs on six hits, striking out five, finishing his career in the World Series as a perfect 3-0 with an ERA of 3.00. Had it not been for the heroics of David Freese, Carpenter could have been the series MVP.

Despite suffering through shoulder problems throughout 2012, Carpenter managed to make three playoff starts in 2012 allowing just four runs in 13.2 innings. After that season, Carpenter tried to make a comeback from the Thoraic Outlet Sydrome, but it was unfortunately too much for the veteran ace. Carpenter finished his career in St. Louis officially retiring after the 2013 season.

He was without a doubt one of the best pitchers in Cardinals’ history and the best free agent signing this team has ever had.

Next: Jeff Suppan

#7 Jeff Suppan 

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Suppan was one of the most perplexing pitchers I have ever seen. Having pitched in Boston, Kansas City, and Pittsburgh before, Suppan signed with the Cardinals in the 2003 offseason. He pitched three seasons in St. Louis and was not very good in the regular season, posting an ERA over four in two of his three seasons in St. Louis and FIP over four in all three seasons. He also gave up over 20 homers in each three seasons.

However, what made Suppan great was his ability to morph into a good pitcher in the postseason. I am not sure where it came from, but it started in his first playoff appearance as he kept the Dodgers at bay in the 2004 NLDS, tossing seven innings, allowing two runs on just two hits, while walking three. Suppan then allowed four runs on eight hits in two starts against the Astros in the LCS. Unfortunately, it ended there for him that year, as the Red Sox got to him for four runs in 4.2 innings in his only appearance in the World Series.

Suppan was back at it again a bit in 2005, as he only allowed one run on three hits and three walks, in five innings against the Astros in the NLCS, getting stuck with the loss. In 2006, Suppan was unable to exit the fifth again, as he gave up three runs in 4.1 innings on six hits and three walks. Suppan then shined in the NLCS against the Mets in two starts. He went a total of 15 innings in the series and allowed just one run, as he pitched the Cardinals to a Game 7 victory and the earned MVP honors for his surprise performance. He even had a solo home run that series.

He put together another quality start in the World Series, going six innings and allowing just three runs on eight hits and two walks.The Cardinals did not see enough value to bring Suppan back to the rotation in 2007 with Adam Wainwright ready to join the rotation. However, Suppan’s postseason performances make him one of the best signings in Cardinals’ history.

Next: David Eckstein

#9 Ryan Ludwick 

Ryan Ludwick came up big in the eighth with his first home run of the season. (Source: stltoday.com)

This was another that I almost left off the list. However, one cannot ignore what Ludwick did in St. Louis. Ludwick had an injury riddled career and was on the path to become one of those prospects who could have become something great, but never made the big leagues. That was until the Cardinals offered Ludwick a minor league deal in the 2006 offseason.

Ludwick was called up on May 6th of 2007 and never was sent back down. He became a fixture in the Cardinals’ lineup for the next 3.5 seasons. He didn’t get the chance to play in all of the playoffs series that the previous guys did. But, he did put up good numbers in the OF for the Cardinals especially in 2008, when he put together a solid all star season, hitting .299/.375/.591, with 80 extra-base hits (40 doubles, 37 homers, 3 triples), posting a 151 OPS+.

That was Ludwick’s best year as a Cardinal, unfortunately he never posted those numbers again with this team, and was dealt in 2010, so that the Cardinals could acquire my least favorite pitcher ever (Jake Westbrook) and probably the most head scratching move John Mozeliak has made yet. Ludwick’s final numbers were really good, .280/.349/.507 and 196 extra-base hits (102 doubles, 84 homers, 6 triples).

Simply due to what Ludwick went through and the Cardinals’ cashing in on what really was a lottery ticket for them, Ludwick goes down as one the best free agent catches for this team.

Next: Carlos Beltran

#10 Carlos Beltran 

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John Mozeliak made the shrewd and surprising move of attempting to replace the gaping hole left by Albert Pujols with Beltran in the 2011 offseason. He could have just let the kids have at it and trust Lance Berkman to play 160 games, however he didn’t. He brought in one of the game’s best available bats in Beltran and it worked. In 2012, Beltran posted a slash of .269/.346/.495 for an 842 OPS. He hit 58 extra-base hits (32 homers, 26 doubles, one triple). Solidly replacing the production lost from Pujols’ exit.

He then continued his unreal postseason success, hitting .444/.542/.944 in the NLDS with two homers and three doubles helping the Cardinals send the Nationals home. He then continued the hot streak into the NLCS against the Giants cooling off just a little, with a slash of .300/.364/.600 with one homer and three doubles in the series loss.

Beltran had another good year in 2o13, .296/.339/.491 was his slash that year, as he chipped in 58 extra-base hits (30 doubles, 24 homers, 3 triples). Beltran then hit an OPS of .944 in the 2013 NLDS, as he hit 2 homers against the Pirates. While, he did not hit a homer in the NLCS (second career postseason series without homer), he did go 6-21 with two doubles and six RBI in that series as the Cardinals beat the Dodgers to advance to the World Series. Where Beltran was 5-17 with 3 RBI in the series loss to the Red Sox.

It was unfortunate that the Cardinals couldn’t get the someday HOF OF a World Series title. However, Beltran will always be one of the best free agent signing in team history.

Next: Honorable Mention

Celebration at Busch Stadium following the Cardinals’ World Series win (Source: Doug Pensinger/MLB.com).

Honorable Mention:

Lance Berkman – Berkman led this team to a World Series title in 2011 and had a great run with the team that year, unfortunately due to his injuries in 2012 he couldn’t be of much help to the team or to this great list.

More from Redbird Rants

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• Cardinals: Adam Wainwright commits to Team USA for the WBC
• Cardinals: Moises Gomez hit 39 home runs, could be in St. Louis in 2023?

Kyle Lohse – Very good signing and renovation by Dave Duncan, could have made this list with a little better postseason career, but it is a strong list that he just couldn’t crack.

Tony Womack – Womack like Sanders was a big reason why the team was so good in 2004. 

Woody Williams  – Williams was another one that could have made this list. Williams finished his Cardinals’ career 45-22 with a 3.53 ERA (3.82 FIP). But, with only two full years and no great performances to make him stick out, he fell short. 

Next: Five free agent pitchers the Cardinals could reboot

There’s your list folks. I hope you enjoyed reading this as much as I enjoyed writing this! Let me know who your favorite free agent signings were in the comments!