MLB Free Agency: Ranking 50 Worst Free-Agent Signings in Baseball History

Joel Reuter@JoelReuterBRFeatured ColumnistNovember 2, 2011

MLB Free Agency: Ranking 50 Worst Free-Agent Signings in Baseball History

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    With the offseason started, the chips will begin to fall on next season's rosters and there are a number of superstar players on the market this year who will command top dollar.

    Signing a player to a big-money, long-term deal always comes with some risk, and for every deal that works out and gives a team a cornerstone player for the next several years, there is one that leaves a team buried under a useless contract.

    So here is a look back at the 50 worst free-agent signings in the history of baseball; moves sure to make fans of the teams involved shudder when looking back on them.

No. 50: Alex Rodriguez, 2001

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    Contract: 10 Years, $252 Million

    Stats During Contract: .304/.400/.591, 329 HR, 908 RBI, 874 R, 52.6 WAR

    While there is little argument that A-Rod was the best player in the game during this contract, what the Rangers gave up, and the return that they received from it, make this contract one of the most disappointing of all time.

    Despite hitting 166 home runs and winning an MVP in his three seasons with the Rangers, the team struggled to 89, 90 and 91 losses during his three seasons with the team. If you are going to pay a player as much money as they did Rodriguez, you look for him to single-handedly make you a contender, and Rodriguez simply didn't do that. 

    He eventually opted out of the contract after his MVP season of 2007, signing another monster deal with the Yankees after that.

No. 49: John Lackey, 2010

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    Contract: Five Years, $82.5 Million

    Stats During Contract: 61 GS, 26-23, 5.26 ERA, 82 ERA+, 264 Ks, 375 IP

    Fresh off an impressive seven-year stretch with the Angels in which he posted a record of 93-67 with a 3.83 ERA while winning double-digit games each season, Lackey was among the top arms on the market heading into the 2010 season.

    His first season in Boston, he won 14 games and had a respectable 4.40 ERA, but this past season he struggled mightily with a 6.41 ERA as he was the worst starter in the American League.

    Now he is set to miss all of next season with Tommy John surgery, and this contract is only getting worse. Unless he comes back strong over the final two years, this one will definitely be moving up the list.

No. 48: Bobby Bonilla, 1992

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    Contract: Five Years, $25 Million

    Stats During Contract: .286/.365/.508, 129 HR, 439 RBI, 406 R, 12.0 WAR

    After starring with the Pirates alongside Barry Bonds and Andy Van Slyke, Bonilla took his talents to The Big Apple in 1992, signing a contract that made him the highest-paid player in baseball at the time.

    What followed was three-and-a-half seasons of mediocrity, as he hit well enough to make a pair of All-Star teams, but came far from justifying being the highest-paid player in the game. He was eventually traded to the Orioles for then-top prospect Alex Ochoa, who turned out to be quite the flop himself.

    Adding to the contract, the Mets bought out the final $5.9 million of his deal but decided to defer payment until 2011, which, with interest, has turned into $29 million the Mets will be paying him for years to come.

No. 47: Torii Hunter, 2008

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    Contract: Five Years, $90 Million

    Stats During Contract: .279/.349/.465, 89 HR, 340 RBI, 315 R, 13.0 WAR

    Hunter was one of the game's most exciting players during his time with the Twins, as he defied gravity with his leaping catches and brought an impressive mix of speed and power offensively.

    However, Hunter was always a good second or third player on a team. While he has continued to put up solid offensive numbers, he is far from producing up to the level of his contract. That is no one's fault but the Angels for overpaying him. 

    Now a right fielder, his defense is no longer the asset it once was and it will be interesting to see where Hunter ends up once his contract is up at the end of next season.

No. 46: Danny Tartabull, 1992

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    Contract: Five Years, $27 Million

    Stats During Contract: .253/.363/.472, 110 HR, 390 RBI, 319 R, 6.5 WAR

    With 124 home runs in five seasons with the Royals, Tartabull had established himself as a legitimate power hitter when he hit the open market in 1992.

    That said, he was by no means the best power hitter in baseball, but the Yankees, nonetheless, made him the highest-paid player in the American League. He did produce one stellar 31 homer and 102 RBI season, but Tartabull was largely a disappointment, and he was dealt to the Athletics during the fourth season of the deal.

    He would later sign a one-year, $2 million contract with the Phillies in 1997 and play just three games, going 0-for-7 before calling it quits as that deal could also make the list.

No. 45: Pedro Martinez, 2005

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    Contract: Four Years, $53 Million

    Stats During Contract: 79 GS, 32-23, 3.88 ERA, 109 ERA+, 464 Ks, 486.2 IP

    While his career was not as long as some of the all-time greats, few would argue that when Martinez was at his best he was one of the best pitchers to ever play the game. From 1997-2003, Martinez went 118-36, 2.20 ERA, 213 ERA-plus, 1,761 Ks, 1,408 innings pitched, taking home three Cy Young awards with another three top-three finishes.

    So when he left in free agency after the Red Sox's World Series win in 2004, it was understandable that he received a big contract. However, after a solid 15-8, 2.82 ERA, 208 Ks in his first season, injuries set in and Martinez made just 48 starts over the next three seasons and was nowhere near the same player.

No. 44: Bartolo Colon, 2004

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    Contract: Four Years, $51 Million

    Stats During Contract: 95 GS, 46-33, 4.66 ERA, 95 ERA+, 422 Ks, 586.2 IP

    This is a tricky one, because during the first two seasons of this contract, Colon was among the best pitchers in all of baseball, as he won 18 games in his first season with the team, then went 21-8, 3.48 ERA, 157 Ks the following season to take home the AL Cy Young award.

    However, after that, he went just 7-13 with a 5.90 ERA in 28 starts over the next two seasons while earning a whopping $30 million over that span.

No. 43: Vince Coleman, 1991

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    Contract: Four Years, $11.95 Million

    Stats During Contract: .260/.320/.351, 7 HR, 96 RBI, 207 R, 149 SB, 0.7 WAR

    Coleman burst onto the scene with the Cardinals in 1985, stealing 110 bases and taking home the NL Rookie of the Year Award. In total, he stole 549 bases in six seasons with the Cardinals, leading the league every season and establishing himself as one of the game's best leadoff hitters.

    When he hit free agency, the Mets jumped at the chance to steal a player from one of their rivals, and Coleman wound up tripling his salary in the process. However, he was immediately a shell of the player he once was on the field, and his off-the-field antics were even worse.

    In 1993, Coleman injured ace pitcher Dwight Gooden, when he accidentally hit him with a golf club that he was swinging in the clubhouse. Then, just three months later, he was charged with endangerment when he threw a lit firecracker into a crowd of autograph seekers, injuring three children in the process. All in all, just a terrible tenure with the Mets.

No. 42: Juan Gonzalez, 2002

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    Contract: Two Years, $24 Million

    Stats During Contract: .288/.327/.517, 32 HR, 105 RBI, 87 R, 0.4 WAR

    After an impressive comeback season with the Indians in 2001 when he hit .325 with 35 homers and 140 RBI, after he struggled the previous season with the Tigers, Gonzalez had a chance at a long-term deal with several teams, but passed it up to return to the Rangers.

    A two-time AL MVP during the 1990s with the Rangers, Gonzalez was far from the player he once was during his second go around, as he battled through injuries and only played 152 games in two seasons and was far from a middle-of-the-order producer. Two years later he was out of baseball, as his decision to pass on the long-term deal cost him.

No. 41: Greg Vaughn, 2000

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    Contract: Four Years, $34 Million

    Stats During Contract: .226/.335/.434, 60 HR, 185 RBI, 185 R, 4.9 WAR

    With some money to spend and looking to make a splash in their third season as a franchise, the Rays went out and signed a number of big-name veterans prior to the 2000 season, but none was bigger than slugger Greg Vaughn.

    After launching 95 home runs the previous two seasons, Vaughn was at the top of his game when he joined the Rays, giving them a star power they had yet to have. However, his career took a sharp downturn, and after two serviceable seasons, Vaughn struggled to a .163 average, eight home runs, 13 RBI line in 2002 before injuries ended his season, and the Rays cut him before the final year of his deal.

No. 40: Kevin Millwood, 2005

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    Contract: Five Years, $60 Million

    Stats During Contract: 156 GS, 52-62, 4.67 ERA, 96 ERA+, 660 Ks, 945.2 IP

    After a solid run with the Braves, Millwood joined the Phillies as a free agent and fell off a bit. When he hit the market again in 2005, the Rangers gave him a shot with a one-year contract, and he responded by leading the league with a 2.86 ERA, despite posting a 9-11 record.

    That was enough for the Rangers to sign him to be their ace the following season, and he was just that in his first season in Texas, winning 16 games, although he posted a 4.52 ERA. He struggled from there on, however, posting ERAs over 5.00 the next two seasons and eventually being dealt to the Orioles before the 2010 season, where he went on to lead the AL with 16 losses while earning $12 million.

No. 39: Jaret Wright, 2005

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    Contract: Three Years, $21 Million

    Stats During Contract: 43 GS,16-15, 5.08 ERA, 88 ERA+, 125 Ks, 214.1 IP

    Wright had a big-time arm and all the potential in the world when he first reached the big leagues in 1997 and helped the Indians to the World Series.

    However, his potential went largely unfilled until the 2004 season, his first-and-only season in the Braves rotation, as he went 15-8, 3.28 ERA, 159 Ks thanks in large part to the tutelage of Leo Mazzone.

    That was enough for the Yankees to shell out some dollars on Wright, and he, along with Carl Pavano, made up a legendarily-awful free-agent class for the Yankees, as Wright only won 16 games over the course of the contract.

No. 38: Eric Gagne, 2008

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    Contract: One Year, $10 Million

    Stats During Contract: 50 G, 4-3, 10 Saves, 5.44 ERA, 38 Ks, 46.1 IP

    There is little question that Gagne was among the best closers of all time when he was in his prime, as his 84 consecutive-converted saves streak was simply amazing.

    That said, Gagne's decline was a rapid one. After leaving the Dodgers to become the Rangers closer, Gagne struggled mightily before being dealt to the Red Sox mid-season. He then posted a 6.75 ERA in 20 appearances for Boston.

    For whatever reason, the Brewers chose to look past how awful Gagne was, signing him to a massive one-year contract to be the team's closer for 2008. It was much of the same, as he eventually lost his job as the team's closer and was out of baseball the following season.

No. 37: Dave Collins, 1982

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    Contract: Three Years, $2.475 Million

    Stats During Contract: .280/.343/.372, 6 HR, 103 RBI, 155 R, 104 SB, 3.1 WAR

    In an effort to shake things up following a loss to the Dodgers in the 1981 World Series, George Steinbrenner put a new emphasis on team speed, and brought in one of the faster players in the game in Collins prior to the 1982 season.

    However, the old adage "you can't steal first" rang true as Collins hit just .253 in his only season with the Yankees, with a meager .315 on-base percentage. The following season, he was dealt to the Blue Jays, along with a young Fred McGriff, for Dale Murray in one of the dumber trades in Yankees history.

    Collins went on to have the best year of his career in the final year of the contract, as he hit .308 while stealing 60 bases and registering a league-best 15 triples as a member of the Jays.

No. 36: Esteban Loaiza, 2006

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    Contract: Three Years, $21.4 Million

    Stats During Contract: 36 GS, 14-15, 5.10 ERA, 87 ERA+, 127 Ks, 219 IP

    Loaiza was a career journeyman when he signed with the White Sox before the 2003 season, at which time he broke out, going 21-9 and finishing second in AL Cy Young voting.

    After the White Sox dealt him to the Yankees for Jose Contreras, Loaiza was still an effective starter in 2004, as well as the following season with the Nationals. That led to a big contract with the A's once he again became a free agent, but at that point Loaiza was already 34 years old.

    After an adequate 11-9, 4.89 ERA season in 2006, Loaiza fell apart and was eventually waived and picked up by the Dodgers, then released twice in 2008 as his career came to an end.

No. 35: Pat Burrell, 2009

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    Contract: Two Years, $16 Million

    Stats During Contract: .218/.311/.361, 34 HR, 128 RBI, 95 R, -1.3 WAR

    Coming off of a World Series win, Pat Burrell turned down a two-year, $22-million offer to remain with the Phillies, hoping to cash in on the open market. However, when his stock was surprisingly low, he had to settle for a smaller contract from the Rays.

    He then proceeded to completely forget how to hit, posting a line of .221 BA, 14 HR, 64 RBI in his first full season with the team, then making it to only May of the second season before being released.

    The Giants, in need of an offensive spark, quickly signed Burrell, and he immediately turned things around, hitting 18 homers with 51 RBI in just 96 games as that was just salt in the wound for the Rays.

No. 34: Jarrod Washburn, 2006

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    Contract: Four Years, $37.5 Million

    Stats During Contract: 117 GS, 32-52, 4.36 ERA, 100 ERA+, 404 Ks, 710.1 IP

    After eight seasons and 75 wins with the Angels, Washburn was an attractive left-handed option once he hit free agency in 2006.

    Coming off of a fine season in which he posted a 3.20 ERA in 29 starts, Washburn was given an ace's contract by the Mariners. While he was a viable starter, he was far from the pitcher he was with the Angels, and his 5-14 season in 2008 was particularly awful.

    He was dealt at the deadline in 2009 to the Tigers for a pair of prospects, and he retired following that season.

No. 33: Jeff Suppan, 2007

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    Contract: Four Years, $42.5 Million

    Stats During Contract: 110 GS, 32-42, 4.95 ERA, 85 ERA+, 335 Ks, 647.1 IP

    From 1999-2006, Suppan established himself as one of the most durable pitchers in all of baseball, averaging 32 starts and 204 innings pitched over that span, while winning double-digits seven times.

    He was especially good with the Cardinals from 2004-2006, going 44-26 and winning the 2006 NLCS MVP, before hitting free agency before the 2007 season. Coming off his strong postseason performance, the Brewers paid him like an ace, but after going 22-22 in his first two seasons, Suppan only got worse.

    He went 7-12 with a 5.29 ERA in 2009 and eventually found himself in the bullpen in 2010 before he was released and scooped up by the Cardinals for 13 late-season starts where he posted a 3.84 ERA.

No. 32: Richie Sexson, 2005

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    Contract: Four Years, $50 Million

    Stats During Contract: .244/.335/.472, 106 HR, 327 RBI, 261 R, 3.0 WAR

    Sexson was a towering power hitter and among the best long ball threats in all of baseball during his time in Milwaukee, as well as in the first two seasons of his contract with the Mariners.

    After that, however, he fell hard, hitting just .205 in his third season and then just .218 the following season, before he was finally released by the Mariners in July of the 2008 season.

    After a brief stint with the Yankees at the end of 2008, Sexson was out of baseball in what was one of the more rapid career declines in recent memory.

No. 31: Aaron Rowand

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    Contract: Five Years, $60 Million

    Stats During Contract: .253/.310/.393, 43 HR, 189 RBI, 194 R, 2.5 WAR

    Rowand was always lauded for his hustle and his all-out style of play, and he was a fan favorite during his stints in Chicago and Philadelphia. In the four seasons leading up to his signing with the Giants, Rowand averaged a line of .289, 19 HR, 68 RBI, 12 steals.

    His production was similar to those numbers in his first two seasons in San Francisco, but that was not nearly enough to justify his $9.6 million annual salary.

    Then things really went south in 2010 as he eventually lost his starting job to Andres Torres, becoming a $13.6 million bench player. It was more of the same in 2011 as he was little more than a fourth outfielder—with one-year, $12 million left on the deal, the Giants will be counting the days until this contract is over.

No. 30: Julio Lugo, 2007

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    Contract: Four Years, $36 Million

    Stats During Contract: .254/.319/.344, 12 HR, 136 RBI, 164 R, 59 SB, -0.1 WAR

    After showing solid potential in his time in Tampa Bay, Lugo was one of the more intriguing free agents of the 2007 class, and he had plenty of suitors.

    In the end, the Red Sox made the richest contract offer, and Lugo rewarded them with a .237 average in his first season, although he did drive in 73 runs and swipe 33 bases.

    He struggled through injuries the following season, and was eventually benched in 2009 before being dealt to the Cardinals for the stretch run. He was dealt again to the Orioles prior to the 2010 season with the Red Sox responsible for $8.85 million of the $9.25 million he was still owed.

No. 29: Juan Pierre, 2007

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    Contract: Five Years, $44 Million

    Stats During Contract: .286/.337/.340, 4 HR, 197 RBI, 373 R, 229 SB, 3.2 WAR

    There is little question that Pierre is one of the fastest players in the game and is a prototypical leadoff hitter. However, $44 million is far too much for a player who is so one-dimensional, as Pierre has zero run-production ability and has one of the worst arms in all of baseball.

    He filled in admirably when Manny Ramirez was suspended, but the Dodgers were wise to cut their losses and deal Pierre to the White Sox three years into the deal for promising young starter John Ely.

    He played well enough as the everyday left fielder for the White Sox over the past two seasons, but it cost the Dodgers $10.5 million over those two seasons which makes the deal that much worse for them.

No. 28: Jeff Blauser, 1998

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    Contract: Two Years, $8.2 Million

    Stats During Contract: .226/.343/.342, 13 HR, 52 RBI, 90 R, 0.4 WAR

    After years as the starting shortstop for the Braves teams that made the playoffs year in and year out, Blauser hit the open market prior to the 1998 season.

    Fresh off of the best year of his career, with a line of .308 BA, 17 HR, 70 RBI, the hype that surrounded the Blauser signing in Chicago was absurd. He then proceeded to hit .219 in his first season with the team, eventually losing his job to Jose Hernandez during the stretch run.

    He was equally terrible the following season, when he was once again the starter, hitting just .240 BA, 9 HR, 26 RBI while getting only 200 at-bats before again losing his job. He would retire the following season.

No. 27: Jamie Navarro, 1997

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    Contract: Four Years, $20 Million

    Stats During Contract: 94 GS 25-49, 6.32 ERA, 73 ERA+, 303 Ks, 575.1 IP

    After back-to-back impressive seasons with the Chicago Cubs, in which he went a combined 29-18 with a 3.62 ERA, Navarro inked a big contract with the South Siders.

    One troubling aspect of his final season with the Cubs was the fact that, despite his 15-12 record and 3.92 ERA, he gave up an NL-worst 244 hits.

    He would not be as lucky when it came to tight-roping around those hits allowed when he got to the White Sox, as he led the AL with 267 hits allowed in his first season, but struggled through a 9-14 season. It only got worse from there, as he went 8-16 and 8-13 with ERAs over 6.00 in his next two seasons, before he was traded to Milwaukee in what turned out to be a great deal for the Sox, as they acquired Cal Eldred and Jose Valentin in the swap.

No. 26: Vernon Wells, 2008

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    Contract: Seven Years, $126 Million

    Stats During Contract: .262/.309/.454, 91 HR, 298 RBI, 286 R, 6.0 WAR

    A homegrown talent and former first-round pick, the Blue Jays watched as Wells emerged as one of the best outfielders in the American League as he averaged a .288 BA, 28 HR, 97 RBI line from 2002-2006.

    However, in his contract year of 2007, Wells had just a .245 BA, 16 HR, 80 RBI. That didn't stop the Blue Jays from locking him up with a massive seven-year deal, though.

    Over his first three years following the contract, his average numbers dropped to .275 BA, 22 HR, 77 RBI and his Gold Glove defense was no longer there. That led the Blue Jays to deal him along with $5 million to the Angles for Juan Rivera and Mike Napoli, and after he hit just .218, the Angels are no doubt regretting that trade and the next three years and $63 million they are stuck with.

No. 25: Alfonso Soriano, 2007

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    Contract: Eight Years, $136 Million

    Stats During Contract: .266/.320/.498, 132 HR, 367 RBI, 354 Runs, 54 SB, 7.8 WAR

    Soriano has been productive as a member of the Cubs since joining the team, so he was not an entire wash like the many others towards the top of this list. That makes it hard to peg just how bad this signing should be considered.

    Coming off of an amazing .277 BA, 46 HR, 95 RBI, 41 SB season with the Nationals, Soriano was the prize of the 2007 offseason, and the Cubs made him one of the richest players in the history of the game.

    While he managed to make the All-Star team in his first two seasons in Chicago, he was hardly the player he once was, as he no longer stole bases as frequently and struggled to top 30 homers.

    Now five years through the contract, Soriano is certainly not getting any better and seems to be as immovable as any player in the majors. This one could continue to creep up this list over the next three years as he will be 38 years old by the time the deal is up.

No. 24: Derek Bell, 2001

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    Contract: Two Years, $9.5 Million

    Stats During Contract: .173/.287/.288, 5 HR, 13 RBI, 14 R, -1.1 WAR

    After a productive career as a member of the Astros' "Killer B's," Bell hit free agency at the age of 31 in 2001, and the Astros chose to let him walk as he was clearly on the downside of his career.

    Hoping he still had something left, the Pirates inked the slugger to a two-year deal. However, after an injury-shortened and highly-ineffective first season, Bell made waves in spring training prior to the 2002 season.

    Upon learning that he would be competing for a starting job, Bell refused to be a part of it, stating that he hadn't competed for a spot since his rookie year and wouldn't do so now, choosing instead to go into "Operation Shutdown" as he called it. By the end of March, he was released and would never play in the majors again.

No. 23: Hideki Irabu, 1997

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    Contract: Four Years, $12.8 Million

    Stats During Contract: 75 GS, 31-25, 5.10 ERA, 90 ERA+, 357 Ks, 450.1 IP

    Irabu will always have a significant place in baseball history, as it was after his signing that the posting system was put in place that is currently used between the United States and Japan.

    However, that is the only reason he will be remembered, as after a storied career in Japan from 1988-1996, he was just awful during his time in the states. And when you are awful in New York, especially after you refuse to play for any other team as Irabu did, your struggles tend to be front page news.

No. 22: Adam Eaton, 2006

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    Contract: Three Years, $24 Million

    Stats During Contract: 49 GS, 14-18, 6.10 ERA, 74 ERA+, 154 Ks, 268.2 IP

    Once considered the better of the two Padres pitching prospects when he and Jake Peavy first entered the big leagues, Eaton got a big deal from the Phillies in 2006 despite a 5.12 ERA in 13 starts with the Rangers the previous season.

    It would be more of the same for the big right-hander, as he went 10-10 in his first season in Philadelphia, but posted a terrible 6.29 ERA in 30 starts. He was again awful the next season, and he did not make it to the end of his contract, as he was released prior to the 2009 season.

No. 21: Todd Hundley, 2001

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    Contract: Four Years, $23.5 Million

    Stats During Contract: .198/.289/.398, 30 HR, 77 RBI, 57 R, -1.1 WAR

    In theory, this was a solid move by the Cubs, as Hundley's father Randy was a Cubs legend and the team was in need of a catcher and middle-of-the-order bat, and Hundley seemingly provided both.

    It couldn't have gone worse, as his first season goes down as one of the worst in baseball history. He hit .187 in 246 at-bats, striking out 89 times which amounts to once every 2.8 at-bats.

    The next season was more of the same, and the Cubs managed to cut their losses heading into the 2003 season when, for some reason, the Dodgers traded Eric Karros and Mark Grudzielanek to the Cubs for Hundley.

No. 20: Milton Bradley, 2009

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    Contract: Three Years, $30 Million

    Stats During Contract: .234/.342/.375, 22 HR, 82 RBI, 101 R, 0.4 WAR

    Always a prickly personality when it comes to his presence in a clubhouse, the Cubs took a chance on Bradley in 2009, as he was coming off the best season of his career after hitting .321 BA, 22 HR, 77 RBI with the Rangers and leading the AL with a .436 OBP.

    However, he slumped badly to open the season and never recovered, sparking a number of ejections and eventually being sent home for the season due to his attitude. The following offseason, the Cubs traded terrible contracts with the Mariners as they took on Carlos Silva's deal.

    This past year he lasted until just May 16th, when the Mariners had finally had enough and released him, likely ending the 33-year-old's career.

No. 19: Matt Young, 1991

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    Contract: Three Years, $6.4 Million

    Stats During Contract: 32 GS, 4-17, 5.01 ERA, 86 ERA+, 191 Ks, 233.2 IP

    Coming off of an 18-loss season, and with a career line of 51-78, 4.26 ERA, 666 Ks, Young was far from a front-of-the-rotation starter, but that did not stop the Red Sox from shelling out a surprising amount of money for the then-32-year-old.

    The money didn't change much, as Young struggled through two seasons with the Red Sox before being released prior to the final season of his contract. He did make headlines on April 12th, 1992, when he pitched an eight-inning no-hitter but took the loss as he walked seven and allowed six stolen bases and two runs.

No. 18: Mark Davis, 1990

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    Contract: Three Years, $14 Million

    Stats During Contract: 109 G, 10-13, 7 Saves, 5.47 ERA, 154 Ks, 184.1 IP

    Coming off of a Cy Young season with the Padres when he posted a line of 4-3, 44 saves, 1.85 ERA, 92 Ks, 92.2 innings pitched, Davis was by far the best relief pitcher on the free-agent market in 1990.

    That by no means meant that he was deserving of being the highest-paid player in the game, but the Royals made him just that when they outbid everyone for his services. He promptly forgot how to pitch and struggled through two-and-a-half seasons with the Royals before being dealt to the Braves.

No. 17: Carlos Silva, 2008

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    Contract: Four Years, $48 Million

    Stats During Contract: 55 GS, 15-24, 5.82 ERA, 74 ERA+, 159 Ks, 296.2 IP

    Coming off of a 13-14 season with the Twins, and with a line of just 47-45, 4.42 ERA, 306 Ks as a starter, the Mariners, for whatever reason, decided to pay Silva like a staff ace.

    He responded with what was easily the worst season of any starting pitcher in 2008, as he went 4-15, 6.46 ERA, 69 Ks, 153.1 innings pitched. The following season was even worse, as he made just six starts, going 1-3 with a lofty 8.60 ERA.

    Heading into 2010, the Cubs and Mariners swapped awful contracts as the Mariners moved Silva and $9 million for Milton Bradley. Silva contributed in Chicago with a 10-6 season in 2010, but made waves last spring when he did not make the rotation and was eventually released.

No. 16: Albert Belle, 1999

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    Contract: Five Years, $65 Million

    Stats During Contract: .289/.374/.509, 60 HR, 220 RBI, 179 R, 3.3 WAR

    After a fantastic run with the Indians, Belle signed a five-year, $55 million contract with the White Sox prior to the 1997 season. Included in the contract was an odd clause that allowed him to demand that he remained one of the three highest-paid players in baseball.

    When he invoked the clause prior to the 1999 season, the White Sox declined to give him a raise and he immediately became a free agent. He then signed with the Orioles, but played just two more seasons before retiring due to a degenerative hip condition.

    The Orioles, however, left him on the 40-man roster the remaining three seasons of his contract and managed to recoup some of the their losses, but he still fell well short of expectations and cost the team a good deal of money.

No. 15: Daisuke Matsuzaka, 2007

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    Contract: 6 Years, $52 Million (plus $51-million posting fee)

    Stats During Contract: 105 GS, 49-30, 4.25 ERA, 108 ERA+, 568 Ks, 622.2 IP

    Never has there been a more hyped-up signing of a foreign player than the media circus that surrounded the Red Sox acquisition of Dice-K prior to the 2007 season.

    After winning the rights to negotiate with Dice-K following a $51 million posting fee, the Red Sox locked him up for six seasons. The early returns were promising, as he went 15-12 in his rookie season, then followed that up with a terrific 18-3, 2.90 ERA, 154 K line that earned him a fourth-place AL Cy Young finish.

    However, injuries have limited him to just 44 starts the past three seasons, and he has been largely ineffective when healthy, going 16-15 with a 5.03 ERA. He is in the final year of the deal, and due to make $10 million—it will be interesting to see what comes of Dice-K once he hits free agency.

No. 14: Gary Matthews Jr., 2007

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    Contract: Five Years, $50 Million

    Stats During Contract: .245/.322/.377, 30 HR, 169 RBI, 185 R, 31 SB, -0.8 WAR

    After spending much of his career as a backup, Matthews finally got a chance to play everyday during the 2005 season for the Rangers. After a solid season, he broke out the following year with a .313 BA, 19 homer, 79 RBI, 10 SB line in what was a contract year.

    The Angels took a chance on the then-32-year-old's breakout season not being a fluke, giving him a massive contract despite his thin track record. After an adequate first season in which he hit .252 BA, 18 HR, 72 RBI, Matthews became an offensive liability and he was dealt to the Mets prior to the 2010 season, but was released by the middle of June.

    He spent the remainder of the season in Class-AAA for the Reds and did not play in 2011, all the while earning $12 million of which $10.9 million came from the Angels.

No. 13: Chan Ho Park, 2002

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    Contract: Five Years, $65 Million

    Stats During Contract: 98 GS, 33-33, 5.56 ERA, 82 ERA+, 409 Ks, 563 IP

    After winning 75 games in five seasons with the Dodgers from 1997-2001, Park was a hot commodity when he hit the market prior to the 2002 season, and the Rangers opened their wallets wide for the then-29-year-old.

    He then proceeded to flop like few have flopped before, never posting an ERA under 5.00 in three-and-a-half seasons with the Rangers. After that, he was dealt to the Padres for another big contract in Phil Nevin, with the Padres paying the final season and $15 million of the deal and getting similar results.

No. 12: Mo Vaughn, 1999

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    Contract: Six Years, $80 Million

    Stats During Contract: .267/.356/.481, 98 HR, 312 RBI, 233 R, 1.8 WAR

    There is little debate that Vaughn was one of the most-feared sluggers of the 1990s, and when he finally left the Red Sox, he still had plenty of pop left in his bat, as he averaged .276, 34 homers, 112 RBI in his first two seasons in Anaheim.

    However, injuries set in in 2001 and he missed the entire season. From there, his weight spiraled out of control and the Angels were forced to cut their losses and deal him to the Mets for starter Kevin Appier. Appier went on to help the Angels to a World Series, while Vaughn struggled through two seasons with the Mets before retiring at the end of 2003.

No. 11: Kevin Brown, 1998

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    Contract: Seven Years, $105 Million

    Stats During Contract: 164 GS, 72-45, 3.23 ERA, 131 ERA+, 917 Ks, 1,078 IP

    After helping the Padres to an improbable World Series run in 1998, Brown hit the free-agent market and became baseball's first $100 million player, as the Dodgers offered Brown nearly $40 million more than anyone else that pursued him.

    Brown won 31 games in his first two seasons in Los Angeles, but injuries struck and his production fell off the following two seasons as he was limited to just 29 starts. He did manage to follow that up with a 14-9, 2.39 ERA, 185 K season in 2003, enough to spark some interest from the Yankees, and the Dodgers dealt the then-39-year-old for Jeff Weaver and cash.

    In two seasons with the Yankees, Brown earned $31.4 million to go 14-13, 4.95 ERA in 35 starts and his time in New York may be best remembered for when he broke his hand punching a clubhouse wall, ending his 2004 season.

No. 10: Wayne Garland, 1977

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    Contract: 10 Years, $2.3 Million

    Stats During Contract: 88 GS, 28-48, 4.50 ERA, 89 ERA+, 241 Ks, 613.1 IP

    The year was 1977, and it was the first offseason of wide-scale free agency in the big leagues. Garland was a 25-year-old starter coming off of a 20-7, 2.67 ERA, 113 K season with the Orioles, and he seemed primed to be one of the game's next big pitchers.

    The Indians decided to lock Garland up while they could, signing him for 10 seasons. He promptly led the American League in losses the following season when he went 13-19, and he was waived just five seasons and 28 wins into his mega deal.

No. 9: Andruw Jones, 2008

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    Contract: Two Years, $36.2 Million

    Stats During Contract: .158/.256/.249, 3 HR, 14 RBI, 21 R, -2.3 WAR

    One of the best power hitters in all of baseball as recently as 2006, few falls from grace have been as swift as that of Andruw Jones.

    After a poor showing in his final season in Atlanta, the Dodgers took a chance on his fall-off being a fluke, and signed him for top dollar. He then proceeded to show up to spring training 20 pounds overweight, and he struggled mightily at the plate the entire season, hitting just .158 in 209 at-bats.

    He was released at the end of the 2008 season, but he has enjoyed a bit of a career resurgence of late as a power bat off the bench for the White Sox and most recently the Yankees.

No. 8: Russ Ortiz, 2005

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    Contract: Four Years, $33 Million

    Stats During Contract: 28 GS, 5-16, 7.00 ERA, 64 ERA+, 67 Ks, 137.2 IP

    Fresh off of a fantastic two-year stint with the Braves in which Ortiz won 36 games, including an NL-best 21 in 2003, Ortiz was among the best starting pitchers available in the 2005 offseason.

    Looking to rebuild after a terrible 111-loss season, the Diamondbacks hoped they had found their ace in Ortiz, but it was not to be. After a rib injury shortened his first season in the desert to just 22 starts and an awful 5-11, 6.89 ERA mark, things only got worse the following season.

    After starting the year 0-5 with a 7.54 ERA in six starts, the Diamondbacks cut Ortiz with $22 million left on his contract in what is one of the most expensive buyouts in baseball history.

No. 7: Darren Dreifort, 2001

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    Contract: Five Years, $55 Million

    Stats During Contract: 86 G, 26 GS, 9-15, 4.64 ERA, 87 ERA+, 221 Ks, 205.2 IP

    Coming off of a solid 12-9, 4.16 ERA, 164 K season in 2000, the Dodgers decided that the 28-year-old Dreifort was a big part of their future and locked him up with a five-year deal despite a career record of 39-45 with a 4.28 ERA to that point in his career.

    Go figure that didn't work out well, as he went 4-7 with a 5.13 ERA in the first season of the contract before being shut down in July and undergoing surgery that would keep him out all of the 2002 season.

    He returned to make 10 adequate starts in 2003 before moving to the bullpen in 2004, where he had his most productive season as the seventh-inning setup man appearing in 60 games with a 4.44 ERA and 11.2 K/9 mark. He would miss all of 2005 with an injury as well, and that was the end of his illustrious career.

No. 6: Kei Igawa, 2007

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    Contract: Five Years, $20 Million (plus $26-million posting fee)

    Stats During Contract: 13 GS, 2-4, 6.66 ERA, 68 ERA+, 53 Ks, 71.2 IP

    After losing out on the Daisuke Matsuzaka sweepstakes to the Boston Red Sox, the Yankees turned their attention to another Japanese pitcher in the then-27-year-old left-hander Igawa, signing him prior to the 2007 season.

    He bounced between the rotation, bullpen and minor leagues in his rookie season, going 2-3 with a 6.25 ERA. Sadly, that is actually his best season to date, as he made just two more big-league appearances since, posting a 13.50 ERA in four innings of work.

    The Yankees have declined to release him, instead letting him play out his contract in the minor leagues. The NY Times had a very good article on him, profiling "The Lost Yankee."

No. 5: Denny Neagle, 2001

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    Contract: Five Years, $51 Million

    Stats During Contract: 65 GS, 19-23, 5.57 ERA, 91 ERA+, 271 Ks, 370.1 IP

    After an impressive run with the Braves in which Neagle went 38-19 in three seasons, including a dazzling 20-5 campaign in 1997, Neagle was traded twice in the span of three years before becoming a free agent prior to the 2001 season.

    Thinking he could reclaim some of his Braves magic and that his ground-ball approach would play well in Colorado, the Rockies inked Neagle to a massive contract. After three seasons and 19 wins, Neagle missed all of 2004 with injury, and then was arrested for soliciting prostitution in 2005, marking the end of his baseball career. The Rockies were able to recover his 2005 salary due to his legal issues.

No. 4: Carl Pavano, 2005

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    Contract: Four Years, $39.95 Million

    Stats During Contract: 26 GS, 9-8, 5.00 ERA, 87 ERA+, 75 Ks, 145.2 IP

    After a breakout season in 2004 with the Marlins when Pavano went 18-8, 3.00 ERA, 139 Ks and finished sixth in NL Cy Young voting, the right-hander cashed in at the expense of the Yankees.

    After starting his Yankees career 4-2 with a 3.69 ERA in his first 10 starts, Pavano injured his elbow which was the beginning of the end for his Yankees career, as he did not pitch at all in 2006 and made just nine starts in 2007 and 2008 combined.

No. 3: Jason Schmidt, 2007

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    Contract: Three Years, $47 Million

    Stats During Contract: 10 GS, 3-6, 6.02 ERA, 72 ERA+, 30 Ks, 43.1 IP

    After six seasons and 78 wins as a member of the Giants, Schmidt had established himself as one of the top pitchers in the game when he hit the free-agent market in 2007.

    He was simply awful for the Dodgers, however, as the team officially paid $15.67 million per win and $4.7 million per start in what goes down as one of the least productive contracts in baseball history.

No. 2: Mike Hampton, 2001

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    Contract: Eight Years, $121 Million

    Stats During Contract: 147 GS, 56-52, 4.81 ERA, 96 ERA+, 458 Ks, 891.1 IP

    After breaking out with a 22-win season in 1999, Hampton was the top free-agent arm when he hit the open market prior to the 2001 season, and the Rockies rewarded him with what was the largest contract in sports history at the time.

    After an uninspired 14-13, 5.41 ERA, 122 K first season with the team, things only got worse for Hampton, and he was dealt to the Braves prior to the 2003 season. After a pair of solid seasons in Atlanta, injuries set in, and Hampton made just 25 total starts from 2005-2008, missing all of 2006 and 2007.

No. 1: Barry Zito, 2007

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    Contract: Seven Years, $126 Million

    Stats During Contract: 43-61, 4.55 ERA, 93 ERA+, 587 Ks, 821.2 IP

    With 102 wins, an AL Cy Young and one of the game's best curveballs to his credit, Zito was the 2007 offseason's top commodity, and he crossed the bay to the National League for what was then a record deal for a pitcher.

    However, he left that curveball along with that ability to win games in Oakland, and he has yet to post a winning season five years into this mega deal. He made just nine starts this past season, along with four relief appearances. At this point, the Giants would almost be better off releasing him and eating the remaining two years of his contract.