A Waste of Money: The 10 Worst Signings in Chicago Cubs History

George DarkowCorrespondent IJune 7, 2011

A Waste of Money: The 10 Worst Signings in Chicago Cubs History

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    Since the inception of free agency in Major League Baseball during the mid 1970s, the winter off-season months of America's pastime have been filled with speculation, anticipation and hope for baseball fans.

    Who can forget the impact made by Reggie Jackson in the 1977 season upon signing with the New York Yankees?  Jackson signed what was considered a monstrous deal ($2.9 million for five years) prior to the 1977 season, and went on to become "Mr. October" later that year.

    Future Hall of Famers like Barry Bonds, Greg Maddux, Nolan Ryan, Manny Ramirez and Catfish Hunter all managed to be instrumental pieces in the growth and eventual success of new teams thanks to free agency.

    For the Chicago Cubs, the result has all too often been less than stellar.  Granted the Cubs have acquired great players via free agency, but more times than not the Cubs have found themselves on the wrong side of a major deal.

    In the history of Cubs free agency, there has been only one player acquired that has gone on to win any sort of major award or be inducted into Cooperstown: Andre Dawson.

    Among numerous factors that have resulted in the Cubs' century-plus of futility, poor free agent signing has been one of the largest.

    Here are the ten worst free agent signings in the history of the Chicago Cubs.

LaTroy Hawkins

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    MESA, AZ - FEBRUARY 25:  LaTroy Hawkins #32 of the Chicago Cubs poses during Spring Training Photo Day at Fitch Park on February 25, 2005 in Mesa, Arizona. (Photo by Jed Jacobsohn/Getty Images)
    Jed Jacobsohn/Getty Images

    After a heart-breaking defeat in the 2003 NLCS, the Chicago Cubs looked to re-tool and make their way back to the post-season in 2004.  Among other needs, the Cubs' top priority in the 2003 offseason was to find a reliable setup man for closer Joe Borowski.

    In Minnesota, the Twins had what many teams considered to be a bullpen savior in LaTroy Hawkins.

    Having posted an ERA of just 1.86 with 75 strikeouts in just over 77 innings as a setup man, Hawkins was sought after by many teams to earn a promotion as their undisputed closer. 

    The Cubs won the battle for the Gary, Indiana native and signed Hawkins to a three-year $11 million deal. 

    An early injury to closer Joe Borowski in 2004 thrust Hawkins into the role of closer, and Hawkins fared well, compiling 25 saves with a low ERA of 2.65.  

    Hawkins' only problem seemed to be his lack of consistency.  In 2004, Hawkins blew 9 saves on the year, including two during a late-September skid that cost the Cubs the National League Wild Card. These blown saves earned him the ire of Cubs fans, who made a habit of booing him loudly at Wrigley Field whenever he was summoned from the bullpen.

    Although Hawkins was never tremendously bad, he never lived up to the expectations of Cubs fans, and by 2005 he was traded to the San Francisco Giants for David Aardsma and Jermore Williams.

Todd Hundley

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    CHICAGO - AUGUST 28:  Catcher Todd Hundley #9 of the Chicago Cubs calls out to his team against the Milwaukee Brewers on August 28, 2001 at Wrigley Field in Chicago, Illinois.  The Brewers defeated the Cubs 8-1.  (Photo by Jonathan Daniel/Getty Images)
    Jonathan Daniel/Getty Images

    Cubs catcher Randy Hundley was one of the most beloved Cubs players in the 1960s and 1970s. Known for being a workhorse behind the plate, Hundley is often regarded as one of the best catchers in Cubs history.

    Randy's son, Todd, was even better.

    As a member of the New York Mets in 1996, Todd Hundley set the Major League record for single-season home runs by a catcher with 41.  By 1997, Hundley was a two-time All-Star and viewed as one of the best catchers in the game.

    In 2001, the son of a former Cubs great got his chance to follow in his father's footsteps as the Cubs signed Hundley to a four-year $23.5 million contract.  

    Unfortunately for the Cubs, Hundley's production had dwindled to the tune of a .187 batting average and an unimpressive 12 home runs.  

    The following season, Hundley wasn't much better, batting .211 with 16  home runs.  One of those home runs—on June 26, 2002—garnered much criticism from Chicago Cubs fans and media as Hundley was believed to have "flipped the bird" to fans as he rounded the bases.  

    Hundley later stated he was gesturing towards heckling Reds fans behind the visiting Cincinnati Reds' dugout but Cubs fans and media believe it was Hundley's response to the all the boos he'd received over the past two seasons.

    With a Cubs career that yielded a batting average of .199, the boos may have been warranted.

    In December of 2007, Hundley was linked to steroids via the Mitchell Report as a player who had taken performance-enhancing drugs.

Danny Jackson

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    1990:  Danny Jackson of the Cincinnati Reds falls after his pitch during a MLB game in the 1990 season. ( Photo by: Otto Greule Jr/Getty Images)
    Otto Greule Jr/Getty Images

    In 1991, the Cubs made their first true big splash in the free agent market.  Hoping to help the Cubs return to the glory they experienced in 1989's NL East division winning season, Cubs general manager Jim Frey went after three major players:  outfielder George Bell and pitchers Dave Smith and Danny Jackson.

    In November of 1990, Jackson entered free agency having just contributed to the World Series victory of his former Cincinnati Reds.  

    Having already enjoyed a fair amount of success in his career—two World Series championships and a 23-win season—Jackson was sought after by the Cubs to be the left-handed compliment to current staff aces Greg Maddux and Rick Sutcliffe.  

    Jackson signed with the Cubs on November 21, 1990 for a then-large $2.6 million per season, and became the second-highest paid member of the Cubs.  

    Unfortunately for the Cubs, they never received much in return for their large investment. Jackson, in 1991, struggled mightily, going 1-5 with a 6.79 ERA before ending his season on the disabled list after just 14 starts.

    In 1992 Jackson returned from injury, but the results weren't much better.  Jackson posted a 4-9 record with an ERA of 4.22 before being traded to the Pittsburgh Pirates for veteran third baseman Steve Buechele.

    Like most former Cubs, Jackson went on to find success after leaving Chicago, and helped the Philadelphia Phillies reach the World Series in 1993.

Dave Smith

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    1990:  Dave Smith of the Houston Astros looks on during a game in the 1990 season. (Photo by Stephen Dunn/Getty Images)
    Stephen Dunn/Getty Images

    An integral part of the 1991 signings that landed pitcher Danny Jackson and outfielder George Bell, Dave Smith was the free agent signed to be the Cubs' closer.

    Having had a fair amount of success for the Houston Astros and accumulating 159 saves over the previous six seasons, Smith was acquired to be the reliable closer the Cubs needed. 

    Signed to a two-year contract worth $4.9 million, Smith was sixth highest-paid player on the Cubs roster and compensated higher than stars Mark Grace and Ryne Sandberg, at the time.

    Smith began the 1991 season by successfully recording saves in his first four chances.  Things began to unravel for Smith after that, though.  By the end of April, Smith had an ERA of 9.53 and had blown three consecutive save opportunities to close out the month.  

    After converting a perfect seven of seven in save opportunities in May, Smith once again became erratic in June.  In July, Smith landed on the disabled list and eventually lost his job as the Cubs' closer to Paul Assenmacher.  

    Smith finished the 1991 season with a 0-6 record and an ERA of 6.00, while saving just 17 games.

    In 1992, Smith was back with Cubs, but injuries kept Smith from returning to his duties as the Cubs' closer.  Smith's career effectively ended on June 8, 1992, as Smith pitched 1.2 innings and surrendered two runs in a 6-4 Cubs win over St. Louis.

    Smith died of a heart attack on December 17, 2008.

Candy Maldonado

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    Rick Stewart/Getty Images

    After the 1992 season, the Cubs were looking for some offensive production to compliment what was turning into a respectable pitching staff.  

    Having decided to not renew future Hall of Famer and fan-favorite Andre Dawson's contract after the regular season, the Cubs and GM Larry Himes found themselves in need of a productive outfielder.

    Candy Maldonado was Himes' answer.

    Fresh off a very productive post-season with the world champion Toronto Blue Jays, Maldonado was signed by the Cubs on December 11, 1992 for $1.65 million - the richest contract Maldonado had ever signed.

    "He's not Andre Dawson", said former Cubs General Manager Larry Himes in 1992, when asked about Candy Maldonado.

    Himes was dead-on about that.

    With expectations high for the Cubs' new outfielder, Maldonado simply never got it going while wearing blue pinstripes.  In 70 games as a Cub, Maldonado managed just three home runs and 15 RBI, while batting an abysmal .186.  By August of the that same season, Maldonado was traded to the Cleveland Indians for Glenallen Hill.

    "I'm not there to be the next Andre Dawson," Maldonado said upon signing with the Cubs.  "He's somebody who's not only a great player and a future Hall of Famer, but the way he carries himself and the way he approaches the game is something you would like to follow. But I'm just going to be Candy Maldonado and give 100 percent every day."

    Evidently, 100 percent of Candy Maldonado is roughly 20 percent of Andre Dawson.  That same year, Dawson hit .277 with 13 homers and 67 RBI for the Boston Red Sox.

Jeff Blauser

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    20 May 1998:  Jeff Blauser, #4 of the Chicago Cubs in action during a game against the Los Angeles Dodgers at Wrigley Field in Chicago, Illinois. The Cubs defeated the Dodgers 5-0. Mandatory Credit: Matthew Stockman  /Allsport
    Matthew Stockman/Getty Images

    In the 1990s, Jeff Blauser was one of the most highly regarded shortstops in the National League.  A member of the Atlanta Braves since his career began in 1984, Blauser's best season was his last in Atlanta.

    In 1997, Blauser batter .305 with 70 RBI and a career-high 17 home runs.  Following that season, Blauser decided to test the free agent market came up big in Chicago.

    The Cubs signed Blauser on December 9, 1997 for two years at $4.2 million per year.

    Unfortunately for the Cubs and Blauser (he had a $7 million team option for a third year), the shortstop's career was heading into a tailspin.  In 1998, Blauser battled injuries and hit a lowly .219 with 4 home runs and 26 RBI.  

    By the time the post-season arrived, Blauser was relegated to reserve status and managed just two pinch-hit at-bats in the best-of-five series against his former Atlanta Braves.  

    Blauser returned in 1999, but wasn't any more effective, hitting .240 with nine homers and 26 RBI, while being moved to a platoon role at second base.

    Blauser retired following the 1999 season.

Kosuke Fukudome

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    CHICAGO - DECEMBER 19:  Chicago Cubs general manager Jim Hendry (R) introduces Japanese Baseball player Kosuke Fukudome #1 (L) as their new outfielder at Wrigley Field December 19, 2007 in Chicago, Illinois.  (Photo by David Blanks/Getty Images)
    David Banks/Getty Images

    As Major League Baseball's presence spread to the Far East, the United States welcomed stars like Seattle's Ichiro Suzuki and the New York Yankees' Hideki Matsui (now of the Oakland Athletics).  

    Seeing the success that these players had found in the United States, Major League clubs began scouting Japanese leagues in search of the next big import.

    In 2007, the Cubs were able to land what many teams regarded as the best player yet to come out of Japan.

    Labeled as a hybrid of the talents of Matsui and Ichiro, Kosuke Fukudome was perhaps the biggest and most intriguing free agent signing in Chicago Cubs history.  Even though Fukudome was a relatively old "rookie" to Major League Baseball, he was labeled a near can't-miss, with the defensive skills and speed of Ichiro Suzuki and the offensive prowess of Hideki Matsui.  

    On December 11, 2007, Cubs General Manager Jim Hendry signed Fukudome to a four-year, $48 million contract.

    In his Major League debut, Fukudome delighted Cubs fans by going three-for-three, including a double on his first Major League pitch and a ninth-inning, game-tying home run off Milwaukee closer Eric Gagne.

    Within days, "Fukudome Fever" was sweeping the nation, and Fukudome's performance was every bit as good as it was believed to be.

    After a promising April and May, Fukudome began to slump miserably.  By August, his once .330 batting average had dropped nearly 100 points, and Fukudome ended his first Major League season with rather mediocre numbers.  

    The following season, Fukudome once again started quick only to fade as the season wore on, and eventually found himself on the bench more often than on the field.

    Currently, Fukudome is the fourth-highest paid player on the Cubs.

Nomar Garciaparra

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    CHICAGO - AUGUST 27:  Nomar Garciaparra #5 of the Chicago Cubs charges toward home plate from his third base position against the Florida Marlins on August 27, 2005 at Wrigley Field in Chicago, Illinois. The Marlins defeated the Cubs 2-1.  (Photo by Jonat
    Jonathan Daniel/Getty Images

    Acquired in the midst of the Cubs' 2004 playoff chase, Garciaparra was supposed to be the piece that would escalate the Cubs past the rival Cardinals.  

    Brought over in a four-way trade involving the Boston Red Sox, Minnesota Twins and Montreal Expos, Garciaparra was acquired by the Cubs and immediately signed to a one-year extension worth $8.25 million.

    In 2004, Garciaparra hit .297 for the Cubs in the 43 games he took part in, but managed only four home runs and 20 RBI.  The Cubs, of course, missed the postseason, while Garciaparra's former team, the Red Sox, won the World Series.

    In 2005, only Kerry Wood and Greg Maddux made more money than Garciaparra, yet Nomar managed another mediocre season, hitting .283 with 9 homers and 30 RBI.  Garciaparra managed to spend a good portion of the season on the disabled list as well.

    After the 2005 season, the Cubs declined to re-sign Garciaparra and he returned to his hometown of Los Angeles where he played for the Dodgers.  Like many former Cubs, Garciaparra returned to form and hit .303 with 20 home runs and 90 RBI in 2006, and received several National League MVP votes.

Alfonso Soriano

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    CHICAGO - MARCH 31: Alfonso Soriano #12 of the Chicago Cubs swings at the pitch against the Milwaukee Brewers during the Opening Day game on March 31, 2008 at Wrigley Field in Chicago, Illinois. (Photo by Jonathan Daniel/Getty Images)
    Jonathan Daniel/Getty Images

    In 2006, word was out that the Chicago Cubs were going to soon be for sale.  As a result of the Tribune Company's quest to sell the franchise, General Manager Jim Hendry was given the green light to spend money on top-dollar free agents.  

    Hendry signed pitchers Jason Marquis and Ted Lilly to start his offseason spending spree and zeroed in on the class of the free agent pool, Alfonso Soriano.

    Hendry seemed intent on landing Soriano, regardless of the price, and on November 20, 2006, Hendry signed Soriano to the richest long-term contract in Cubs history - 8 years, $136 million.

    In signing Soriano, the Cubs thought they would be receiving a player who would hit 30-plus home runs and steal 30-plus bases per year.  Health, of course, was the variable that nobody could predict.

    On August 5, 2007, Soriano suffered from a torn quadriceps in a Sunday night game against the New York Mets - which also happened to be the game credited as Tom Glavine's 300th victory. Since the injury to his leg, Soriano has been nothing close to the baserunner he once was. Averaging 35 stolen bases in each of his first six seasons, Soriano has stolen just 33 over the past three.

    In addition to Soriano's loss of speed, his entire repertoire has diminished since joining the Cubs. Over the course of his three-plus seasons in Chicago, Soriano's power numbers, run-production numbers, and defensive abilities have all incrementally diminished.

    Currently, Soriano stands to make a team-high $19 million in 2011 and $18 million through 2014.

Milton Bradley

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    CHICAGO - JUNE 17: Milton Bradley #21 of the Chicago Cubs swings at the pitch during the game against the Chicago White Sox on June 17, 2009 at Wrigley Field in Chicago, Illinois. (Photo by Jonathan Daniel/Getty Images)
    Jonathan Daniel/Getty Images

    In 2009, Cubs General Manager Jim Hendry took a big risk.  Entering the season, manager Lou Piniella stated his team needed an outfielder capable of hitting for power and driving in runs.  After looking into the free agent pool, Jim Hendry's best option came in the form of MLB head-case Milton Bradley.

    Having a reputation for feuding with just about anybody involved in the game of baseball—teammates, managers, coaches, umpires, fans, even radio broadcasters— Bradley was signed by the Cubs to a three-year $30 million deal and preached that he was a good guy who had been miscast as a problem child of sorts.

    Bradley started the 2009 season slowly, batting under .200 for the first month and a half and gradually improved to what would best be called a mediocre season.  

    In addition to Bradley's production woes, Bradley was an extremely difficult personality for manager Lou Piniella to corral.  On numerous occasions, Bradley and Piniella had heated verbal exchanges—one of which resulting in Piniella calling Bradley "a piece of [expletive]"—until Cubs GM Jim Hendry had finally had enough.  

    On September 20, 2009 Milton Bradley was suspended for the remainder of the season and subsequently traded to the Seattle Mariners on December 18, the same year.

    Unfortunately for Jim Hendry, the Bradley signing may be the most definitive move of his career.


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