MLB Free Agency: 50 Biggest Free-Agent Busts of All Time

Dan Tylicki@DanTylickiAnalyst IDecember 28, 2010

MLB Free Agency: 50 Biggest Free-Agent Busts of All Time

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    DENVER - MAY 1:  Starter Mike Hampton #32 of the Atlanta Braves delivers a pitch against the Colorado Rockies in the fifth inning at Coors Field on May 1, 2004 in Denver, Colorado.  The Rockies won 3-2; while Hampton got no decicion on five innings pitche
    Brian Bahr/Getty Images

    The baseball offseason is characterized by the free agency movement, where players sign with teams for top dollar. It seems as if every year, another free agent breaks the record for biggest contract. When these major deals in particular don't work out, then they hurt the organization big time.

    It seems to happen all too often; a player is signed to a major contract only to fail miserably, whether it's due to injury or ineffectiveness. Even as early as last year, we could find contracts that did not work out, and now that salaries have exploded, this will continue to happen. As for these 50 free agent busts, they're just happy that, for most of them, they're past this experience.

50. Andy Messersmith, Atlanta Braves

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    This Dodgers pitcher was one of the original free agents that helped to get the ball rolling on the market, and signed with the Atlanta Braves to a three-year, $1 million deal, big in 1977.

    After coming off two Cy Young-caliber seasons, winning 20 and 19 games in two years, he went 11-11 in his first year with the Braves. After a worse second season, the Braves were able to get rid of the last year of his deal when the Yankees purchased him, where he played in six games.

49. Dave Collins, New York Yankees

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    TUCSON - FEBRUARY 28:  Coach Dave Collins #29 of the Colorado Rockies during the 2004 MLB Spring Training Photo Day at Hi Corbett Field on February 28, 2004 in Tucson, Arizona. (Photo by Harry How/Getty Images)
    Harry How/Getty Images

    Collins had a decent career and was a nice role player that the Yankees wanted. As a result, they signed him to $650,000 a year in 1982, star money, despite only playing a full season once. He had an okay year, but the Yankees realized their mistake and quickly traded him away in a package that included a young Fred McGriff.

48. Roger Clemens, New York Yankees

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    WASHINGTON - DECEMBER 8:  Roger Clemens arrives at Federal Court December 8, 2010 in Washington, DC.  Clemens, a former Major League Baseball pitcher, appeared at court for an interim status conference on charges he lied to Congress during a hearing on th
    Brendan Smialowski/Getty Images

    Normally I would not consider the stretch of a 44 year old to be a bust, but with the money the Yankees paid him, it has to be included. After coming over a good spot year with Houston, He signed a one-year deal worth $28,000,022. He pitched .500 ball in 18 starts and faltered in the playoffs.

47. Matt Young, Boston Red Sox

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    Another early 90s Red Sox move I can't figure out. He spent the 1990 season with the Mariners, where he went 8-18. The Red Sox felt that he just had a hard luck season, and signed him to a contract worth over $2 million a year. He started 24 games in two years and won only three games. He's not higher because his expectations could not have been that great.

46. Carlos Beltran, New York Mets

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    NEW YORK - SEPTEMBER 18:  Carlos Beltran #15 of the New York Mets in action against the Atlanta Braves during their game on September 18, 2010 at Citi Field in the Flushing neighborhood of the Queens borough of New York City.  (Photo by Al Bello/Getty Ima
    Al Bello/Getty Images

    The Mets get a lot of flack for this deal, when it really wasn't all that bad. He's made four All-Star appearances as a Met, and after struggling out of the gate, his next few seasons were really good. Unfortunately, he has only played the half the season in 2009 and 2010, and the contract has went from good enough to bust potential.

45. Juan Pierre, Los Angeles Dodgers

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    LOS ANGELES, CA - OCTOBER 16:  Juan Pierre #9  of the Los Angeles Dodgers looks on during warm ups prior to the start of Game Two of the NLCS against the Philadelphia Phillies during the 2009 MLB Playoffs at Dodger Stadium on October 16, 2009 in Los Angel
    Stephen Dunn/Getty Images

    This one may not be Pierre's fault. After a great year with the Cubs, he was available for any team that needed a dependable leadoff hitter. The Dodgers signed him to a three-year deal, making $10 million his final year. His first season went as expected, then the Dodgers brought in two players that forced Pierre to the bench.

    Who were those two players? Well, both happen to be coming up later in the rankings.

44. Storm Davis, Kansas City Royals

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    KANSAS CITY, MO - 1991:  Storm Davis #43 of the Kansas City Royals delivers a pitch during a game in July of 1991 at Royals Stadium in Kansas City, Missouri.  (Photo by Jonathan Daniel/Getty Images)
    Jonathan Daniel/Getty Images

    The Royals decided to jump into the free agent market in 1990, and signed Storm Davis to a seven-figure per year deal after a 19-win season at Oakland. He went 7-10 his first season, then was relegated to bullpen duty the following year. The Royals ended up trading him to Baltimore to get rid of a deal that never came close to working out.

43. Manny Ramirez, Los Angeles Dodgers

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    BOSTON - SEPTEMBER 05:  Manny Ramirez #99 of the Chicago White Sox pinch hits in the eighth inning against the Boston Red Sox on September 5, 2010 at Fenway Park in Boston, Massachusetts.  (Photo by Elsa/Getty Images)
    Elsa/Getty Images

    Manny Ramirez had many great years in Boston, and in 2008, he was traded to the Dodgers. In 53 games he hit nearly .400. As a result, the Dodgers signed him to an immense two-year deal worth over $40 million. He played well in between a 50-game suspension and injury, but he was far from what the Dodgers paid for.

    The first of the duo to relegate Juan Pierre to the bench.

42. Aramis Ramirez, Chicago Cubs

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    CHICAGO - SEPTEMBER 05: Aramis Ramirez #16 of the Chicago Cubs hits his 22nd home run of the year, a two run shot in the 3rd inning, against the New York Mets at Wrigley Field on September 5, 2010 in Chicago, Illinois. (Photo by Jonathan Daniel/Getty Imag
    Jonathan Daniel/Getty Images

    Much like Carlos Beltran, he was signed to a huge, multi-year deal and started off well, but has had problems the last two years. He still has a couple years left on the deal to get himself off this list, though it looks unlikely.

41. Greg Vaughn, Tampa Bay Devil Rays

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    ST. PETERSBURG, FL- FEBRUARY 22:  Greg Vaughn #23 poses for a portrait during the Tampa Bay Devil Rays Media Day at Florida Power Park on February 22, 2003 in St. Petersburg, Florida. (Photo by: Ezra Shaw/Getty Images)
    Ezra Shaw/Getty Images

    Vaughn seemed to come out of nowhere and have great 1998 and 1999 seasons. As a result, the Tampa Bay Rays signed him to a big three-year deal worth almost $25 million. He responded with two okay seasons and one awful one, hitting .163 in 69 games.

40. Kevin Brown, Los Angeles Dodgers

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    LOS ANGELES - AUGUST 24:  Starting pitcher Kevin Brown #27 of the Los Angeles Dodgers delivers a pitch during the National League game against the New York Mets at Dodgers Stadium on August 24, 2003 in Los Angeles, California. The Mets defeated the Dodger
    Doug Benc/Getty Images

    I don't think this one is that awful, but he appears on most bust lists, so he's included. He finished an 18-game winning season with the Padres, and signed with the Dodgers for $100 million.

    Brown actually had four very good years with the Dodgers, though one was injury-riddled. He kept an ERA of 3.00 or lower in all four seasons at the height of the steroid era, and made a couple All-Star appearances in the process.

    The Dodgers overpaid, but he played as well as he played anywhere in his career, so if he's a bust, that's the Dodgers' fault.

39. Richie Sexson, Seattle Mariners

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    NEW YORK - MAY 24:  Richie Sexson #44 of the Seattle Mariners walks on the field against the New York Yankees during their game on May 24, 2008 at Yankee Stadium in the Bronx borough of New York City. (Photo by Chris McGrath/Getty Images)
    Chris McGrath/Getty Images

    Richie Sexson had a few very good years in Milwaukee, but struggled in Arizona in 2004. Despite this, the Seattle Mariners signed him to a $50 million deal over four years. He had two years of 35+ doubles and HR and 100+ RBI, and seemed to perform as advertised.

    In the final two years of his deal, he stopped hitting, could barely break .200 and finished both years with negative WAR. He performed no better with the Yankees, where he ended his career.

38. George Foster, New York Mets

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    FLUSING, NY - 1985:  George Foster #15 of the New York Mets takes a swing during a game in 1985 at Shea Stadium in Flushing, New York.  (Photo by Rick Stewart/Getty Images)
    Rick Stewart/Getty Images

    The second of three guys signed for power but failed to produce, George Foster was a beast during his time on the Reds. In 1982, he signed with the Mets for five years, making nearly $3 million his final year. His average was no longer good, and he still had some power, but he was a shell of his former self and not worth what the Mets paid.

37. Jason Giambi, New York Yankees

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    DENVER - SEPTEMBER 15:  Jason Giambi #23 of the Colorado Rockies looks on from the dugout against the San Diego Padres at Coors Field on September 15, 2010 in Denver, Colorado. The Rockies defeated the Padres 9-6.  (Photo by Doug Pensinger/Getty Images)
    Doug Pensinger/Getty Images

    Giambi was coming off two amazing seasons with Oakland, so naturally the Yankees threw him as much money as they could, over $20 million a year for his final three years. His power remained mostly intact, but his batting average went from .308 in Oakland to .260 in New York, aside from missing a large part of two seasons.

    I'm not sure how he's still in the league.

36. Adrian Beltre, Seattle Mariners

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    SEATTLE - SEPTEMBER 15:  Adrian Beltre #29 of the Boston Red Sox bats against the Seattle Mariners at Safeco Field on September 15, 2010 in Seattle, Washington. (Photo by Otto Greule Jr/Getty Images)
    Otto Greule Jr/Getty Images

    There's a reason Beltre is not getting signed to the amount he may want. After an amazing season for the Dodgers in 2004, he signed a big contract with the Seattle Mariners. In five seasons, he played decently and won a couple Gold Gloves, but was not a star.

    In 2010 with the Boston Red Sox, he had an amazing year again, which ironically just makes him look worse, as it made him seem like he only plays well in contract years.

35. Steve Kemp, New York Yankees

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    Yet another player who had some power in the 80s, the Yankees signed him to a multi-year deal in 1983 for five years and $5.45 million.

    He was worth perhaps a fourth of that after playing just over half the season in the two years he played for the Yankees. He was shipped to Pittsburgh after the 1984 season, and was even worse there.

34. Ken Griffey, Jr., Cincinnati Reds

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    SEATTLE - MAY 31:  Ken Griffey Jr. #24 of the Seattle Mariners bats against the Minnesota Twins at Safeco Field on May 31, 2010 in Seattle, Washington. (Photo by Otto Greule Jr/Getty Images)
    Otto Greule Jr/Getty Images

    When the Reds signed him to a contract after the 1999 season, he was THE free agent, and in his prime, was on pace to be one of the best players of all time.

    In Cincinnati, he was very good when healthy, but unfortunately, he just wasn't all that healthy. The expectations going into Cincinnati compared with the end result may label him as a bust, though he's still a first-ballot Hall of Famer when the time comes.

33. Ed Whtison, New York Yankees

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    1990:  Pitcher Ed Whitson of the San Diego Padres throws a pitch during a game at Jack Murphy Stadium in San Diego, California. Mandatory Credit: Ken Levine  /Allsport
    Ken Levine/Getty Images

    Another player who had problems with the Yankees for some reason. After a solid season with San Diego, he signed with the Yankees for the 1985 and 1986 seasons.

    Whitson pitched okay in 1985, but struggled badly the year after that, finishing his Yankees tenure with an ERA of 5.36. He had several good years with San Diego after rejoining them, making him look decent in the end.

    Some people just should not pitch for the Yankees.

32. Danny Tartabull, New York Yankees

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    2 Aug 1995:  Outfielder Danny Tartabull of the Oakland Athletics at bat  during a game against the Texas Rangers at the Oakland Coliseum in Oakland, California.  The Rangers won the game 5-4. Mandatory Credit: Otto Greule  /Allsport
    Otto Greule Jr/Getty Images

    In 1991, Tartabull had a career year with the Royals, hitting .316 with 31 home runs. The Yankees needed some power and signed him to a deal worth over $5 million a year. He provided good power for a couple years, then struggled and was sent to Oakland. Not the worst move by the Yankees, but they were hoping for a lot more from him.

31. Alfonso Soriano, Chicago Cubs

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    SAN FRANCISCO - AUGUST 12:  Alfonso Soriano #12 of the Chicago Cubs bats against the San Francisco Giants during an MLB game at AT&T Park on August 12, 2010 in San Francisco, California.  (Photo by Jed Jacobsohn/Getty Images)
    Jed Jacobsohn/Getty Images

    You know what the worst part of this deal is? He still has four years left, so this contract still has the possibility to become a true stinker. He could still rebound too, but that seems unlikely now.

30. Matt Morris, San Francisco Giants

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    SAN FRANCISCO - AUGUST 10:  Matt Morris #35 of the Pittsburgh Pirates pitches against the San Francisco Giants during a Major League Baseball game at AT&T Park August 10, 2007 in San Francisco, California.  (Photo by Lisa Blumenfeld/Getty Images)
    Lisa Blumenfeld/Getty Images

    Matt Morris was a big piece of the Cardinals rotation, and they seemed to let him go just in time. He signed with the San Francisco Giants to a big three-year deal, and went 10-15 his first year, 7-7 his second and was traded to the Pirates where he ended his career.

29. Julio Lugo, Boston Red Sox

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    LOS ANGELES, CA - AUGUST 19:  Julio Lugo #12 of the St. Louis Cardinals looks to make throw against the Los Angeles Dodgers at Dodger Stadium on August 19, 2009 in Los Angeles, California.  (Photo by Jeff Gross/Getty Images)
    Jeff Gross/Getty Images

    After Lugo struggled with the Dodgers when he was traded to them in 2006, the Boston Red Sox decided to take a chance on him, and gave him a contract worth nearly $10 million a year. He only played one full season with the team, and hit .237 in it. His best WAR as a Red Sox player? 0.4.

28. Mark Davis, Kansas City Royals

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    Gary Newkirk/Getty Images

    When you acquire a Cy Young winner through free agency, you expect him to be good. For the Royals and Mark Davis, that didn't work out. He signed a deal worth over $3 million a year, and in three seasons with the Royals, he went 9-13 with a 5.31 ERA.

27. Danny Jackson, St. Louis Cardinals

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    1990:  Danny Jackson of the Cincinnati Reds winds back to  pitch during a MLB game in the 1990 season. ( Photo by: Scott Halleran/Getty Images)
    Scott Halleran/Getty Images

    The Cardinals usually do a great job on selecting the right starting pitchers, but even they mess up. In 1995, the Cardinals signed Jackson to a three-year deal worth around $10 million. He went from a 14-6 record in 1994 with the Phillies to a 2-12 record and a 5.90 ERA, and never got any better for the Cardinals.

    Unlike others on the list who retreated to the Padres after the bust, he couldn't even pitch in San Diego after being traded there.

26. Kevin Millwood, Texas Rangers

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    ST. PETERSBURG, FL - SEPTEMBER 29:  Pitcher Kevin Millwood #34 of the Baltimore Orioles pitches against the Tampa Bay Rays during the game at Tropicana Field on September 29, 2010 in St. Petersburg, Florida.  (Photo by J. Meric/Getty Images)
    J. Meric/Getty Images

    In 2005, Millwood had the definition of a hard luck season with the Indians. He had a record under .500, yet led the league with an ERA of 2.86. As a result, the Texas Rangers signed him to a four-year contract worth about $48 million. He was a starter all four years, which is better than we can say about some, but his ERA was over 5.00 in two seasons, and he was nowhere near the ace the Rangers were hoping for.

25. Nick Esasky, Atlanta Braves

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    1988:  Nick Esasky of the Cincinnati Reds swings at the pitch during a MLB game in the 1988 season. ( Photo by: Jonathan Daniel/Getty Images)
    Jonathan Daniel/Getty Images

    This one was the victim of bad luck, rather than the team making a bad call of the player suddenly sucking. After having a career year with the Red Sox in 1989, Esasky signed with the Atlanta Braves and signed for three years in a deal worth nearly $6 million. He played only nine games for the Braves, as vertigo ended his career early.

    He spent some time in the minors in 1992 to try to make a comeback, but it didn't work out.

24. Russ Ortiz, Arizona Diamondbacks

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    MIAMI - APRIL 09:  Relief pitcher Russ Ortiz #48 of the Los Angeles Dodgers pitches in the ninth inning against the Florida Marlins during the Marlins home opening game at Sun Life Stadium on April 9, 2010 in Miami, Florida. The Dodgers defeated the Marli
    Doug Benc/Getty Images

    Ortiz had two very good years with the Atlanta Braves when the Diamondbacks signed him to a four-year deal. However, he pitched so badly that he was cut a year-and-a-half into it. He went 5-16 with an ERA of 7.00 as a member of the D'backs.

23. Barry Zito, San Francisco Giants

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    SAN FRANCISCO - OCTOBER 02:  Barry Zito #75 of the San Francisco Giants walks off the field after the first inning against the San Diego Padres at AT&T Park on October 2, 2010 in San Francisco, California.  (Photo by Justin Sullivan/Getty Images)
    Justin Sullivan/Getty Images

    Zito finally seems to be pitching okay with the Giants, having turned into a solid number four or five option. The problem with that is that he was meant to be an ace, and is paid as such. He's being paid over $18 million a year to pitch .500 baseball with an ERA around four. He has time to rebound and pitch well again, but that time is running out fast.

22. Mo Vaughn, California Angels

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    PORT ST. LUCIE, FL - FEBRUARY 25: Mo Vaughn of the New York Mets poses for a portrait during media day at Thomas J. White Stadium on February 25, 2003 in Port St. Lucie, Florida.  (Photo by Fernando Medina/Getty Images)
    Fernando Medina/Getty Images

    The big man on campus was one of the big power hitters of the 90s, and as a result, the Angels signed him from the Boston Red Sox to a six-year, $80 million contract. He started off well with the Angels, having two great power seasons before disappearing for a year

    It was Mo Vaughn's three-year deal with the Mets however, which was worth nearly $50 million, that sealed this as a bust. After missing the 2001 season while with California, he was nowhere near the hitter he was while he was with the Mets.

21. Gary Matthews, Jr., Los Angeles Angels Of Anaheim

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    PHILADELPHIA - MAY 2: Center fielder Gary Matthews Jr. #19 of the New York Mets stands at the plate during a game against the Philadelphia Phillies at Citizens Bank Park on May 2, 2010 in Philadelphia, Pennsylvania. The Phillies won 11-5. (Photo by Hunter
    Hunter Martin/Getty Images

    I'm still not sure what compelled the Angels to make this move. Nonetheless, in 2006, Gary Matthews finally had a very good year with the Texas Rangers, hitting .313 in 147 games, both career highs.

    The Angels signed him to a five-year, $50 million deal, and he played a full year in 2007, then was put on bench duty after that. He was shipped to the Mets for the 2010 season.

    The worst part? He may not play in the majors next year and the Angels still have a year left to pay him.

20. Danys Baez, Baltimore Orioles

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    PHILADELPHIA - MAY 2: Relief pitcher Danys Baez #55 of the Philadelphia Phillies delivers a pitch during a game against the New York Mets at Citizens Bank Park on May 2, 2010 in Philadelphia, Pennsylvania. The Phillies won 11-5. (Photo by Hunter Martin/Ge
    Hunter Martin/Getty Images

    When he was a rising prospect in Cleveland, I didn't feel the hype at all. I still don't get what the draw was. After he had an average year in relief in 2006, the Baltimore Orioles signed him to a three-year, $19 million deal. His statline was 4-12 with a 5.02 ERA while not playing in the majors in the middle year.

    He now plays for the Phillies, where he's...actually still very mediocre. At least his $2.75 million salary is somewhat more realistic than Baltimore's.

19. Aaron Rowand, San Francisco Giants

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    ARLINGTON, TX - NOVEMBER 01:  Aaron Rowand of the San Francisco Giants bats against the Texas Rangers in Game Five of the 2010 MLB World Series at Rangers Ballpark in Arlington on November 1, 2010 in Arlington, Texas. The Giants won 3-1.  (Photo by Ronald
    Ronald Martinez/Getty Images

    Everyone was iffy about Jayson Werth's contract after coming out of nowhere to have a great year in a rare full season for him. Exhibit A on why he could become a bust is Aaron Rowand. In 2007, he had his second great year, hitting .309 and winning a Gold Glove, and as a result the Giants signed him to a five-year, $60 million contract.

    The output? Two decent seasons, and he's now riding the bench for the Giants as they try to pay off the rest of the contract. In 2010, he hit .230 and only seems to be getting worse.

18. Juan Gonzalez, Texas Rangers

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    ARLINGTON, TX - APRIL 10:  Juan Gonzalez #19 of the Texas Rangers swings at a pitch during the game against the Oakland Athletics at the Ballpark in Arlington on April 10, 2003 in Arlington, Texas.  The Rangers defeated the A's 5-4.  (Photo by Ronald Mart
    Ronald Martinez/Getty Images

    Juan Gonzalez was showing signs of slowing down when he signed with the Indians in 2001. He had a comeback year, hitting .325 and finishing fifth in MVP voting. As a result, Texas wanted him back and they signed him for two years with a contract worth $24 million. He played 152 combined games, and while he hit well enough while active, it was a waste of money for a guy on the downswing.

17. Steve Karsay, New York Yankees

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    TAMPA, FL - MARCH 7:  Pitcher Steve Karsay #31 of the New York Yankees delivers against the Cleveland Indians during an MLB Spring Training game at Legends Field on March 7, 2005 in Tampa, Florida. The Indians defeated the Yankees 3-1. (Photo by Doug Pens
    Doug Pensinger/Getty Images

    Another one on the "good when active list," the Yankees signed Karsay to a four-year, $22.5 million contract. For starters, they signed a reliever for that much. He actually had a good first year in 2002, going 6-4 with a 3.26 ERA. However, he missed the next season due to shoulder surgery, and never really regained his form on the diamond.

16. Derek Bell, Pittsburgh Pirates

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    14 Mar 2000:  Derek Bell #16 of the New York Mets looks on during the Spring Training Game against the Florida Marlins at the Thomas White Stadium in Port St. Lucie, Florida. Mandatory Credit: Matthew Stockman  /Allsport
    Matthew Stockman/Getty Images

    After having a decent season for the Mets in 2000, Bell was signed by the Pittsburgh Pirates for $5 million. He hit .173 and flat out stunk for the Pirates, and then came Operation Shutdown. That's something to look up for yourself (just because it's hard to believe), but essentially the Pirates paid him in 2002 to not play for the team and to go home.

15. Bobby Bonilla, New York Mets

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    14 Jun 1998:  Bobby Bonilla #25 of the Los Angeles Dodgers in action during a game against the Colorado Rockies at the Dodger Stadium in Los Angeles, California.  The Rockies defeated the Dodgers 3-2. Mandatory Credit: Vincent Laforet  /Allsport
    Vincent Laforet/Getty Images

    Maybe Bell was revenge for this. After having two amazing years with the Pirates, Bonilla signed with the Mets before the 1992 season for five years and $29 million. His production was decent, but it wasn't even close to what he was pulling off in Pittsburgh, and they sent him to Baltimore in 1995.

    His second contract with the Mets is quite likely the worst one in history, as the Mets are paying it off indefinitely.

14. Milton Bradley, Chicago Cubs

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    CHICAGO - JULY 26: Milton Bradley #15 of the Seattle Mariners takes a swing against the Chicago White Sox at U.S. Cellular Field on July 26, 2010 in Chicago, Illinois. The White Sox defeated the Mariners 6-1. (Photo by Jonathan Daniel/Getty Images)
    Jonathan Daniel/Getty Images

    I'm not sure which move is worse, the Cubs offering this contract, or the Mariners trading for it. Probably the latter. The Cubs offered him a three-year, $30 million deal after having a very good season with the Rangers. Bradley struggled with the Cubs, and his time with the Mariners so far...well, saying it's been bad doesn't really do it justice.

13. Vince Coleman, New York Mets

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    2 Mar 1998:  Vince Coleman #29 of the St. Louis Cardinals in action during their 13-5 win over the Los Angeles Dodgers during Spring Training at the Roger Dean Stadium in Jupiter, Florida. Mandatory Credit: Stephen Dunn  /Allsport
    Stephen Dunn/Getty Images

    Coleman was one of the baserunning showstoppers of the 1980s, running wild for the Cardinals. Once he signed a three-year deal with the Mets though, suddenly that was it. He stats took a nosedive, he never played a full season and his off-the-field antics were infamous. When you spend much of your salary on Bonilla and Coleman, of course the team's not going to work.

12. Darren Dreifort, Los Angeles Dodgers

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    LOS ANGELES - APRIL 5:  Darren Dreifort #37 of the Los Angeles Dodgers pitches against the San Diego Padres on April 5, 2004 at Dodger Stadium in Los Angeles, California. The Padres defeated the Dodgers 8-2 in the season opener for both teams.  (Photo by
    Doug Benc/Getty Images

    When you allow a player to enter free agency and you end up re-signing him, how could it go wrong? In the case of Darren Dreifort, it can go very wrong. He was signed to a five-year, $55 million deal, Injuries took their toll, as he was sidelined most of the time. His statline during the contract was 9-15, a 4.64 ERA and just over 200 innings pitched.

11. Chan Ho Park, Texas Rangers

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    NEW YORK - OCTOBER 29:  Chan Ho Park #61 of the Philadelphia Phillies throws a pitch against the New York Yankees in Game Two of the 2009 MLB World Series at Yankee Stadium on October 29, 2009 in the Bronx borough of New York City.  (Photo by Chris McGrat
    Chris McGrath/Getty Images

    The Rangers seem to have no luck with pitching. After a solid 2001 season with the Dodgers, the Rangers signed Park to a five-year, $65 million contract. He pitched badly for three-and-a-half seasons, and he was eventually traded to where every pitcher goes when they want to revive their career, the Padres.

10. Kei Igawa, New York Yankees

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    TAMPA, FL - MARCH 5: Pitcher Kei Igawa #17 of the New York Yankees throws in relief against the Tampa Bay Rays March 5, 2010 at the George M. Steinbrenner  Field in Tampa, Florida. (Photo by Al Messerschmidt/Getty Images)
    Al Messerschmidt/Getty Images

    Perhaps the worst of the Yankees' signings. It wasn't for all that much money, $20 million over five years. However, he's made 13 career starts and gotten two wins as he languishes in the minor leagues. Just because the Red Sox got Dice-K, the Yankees felt obligated to get Igawa.

    But was he the biggest free agent bust for the Yankees? No. We all know what is...

9. Carl Pavano, New York Yankees

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    MINNEAPOLIS - OCTOBER 07:  Carl Pavano #48 of the Minnesota Twins delivers a pitch in the first inning against the New York Yankees during game two of the ALDS on October 7, 2010 at Target Field in Minneapolis, Minnesota.  (Photo by Elsa/Getty Images)
    Elsa/Getty Images

    If you mention his name to a Yankees fan, an instant stomach ache ensues. After Pavano's career year for the 2003 Florida Marlins, the Yankees signed him to a $40 million contract for four years. Injuries relegated him to 26 starts and nine wins.

    In 2010, we see the exact same situation, though the Yankees are not going to go near him, whether they need pitching or not.

8. Darryl Strawberry, Los Angeles Dodgers

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    NEW YORK - APRIL 05: Former New York Mets player, Darryl Strawberry throws out the ceremonial first pitch prior to the game between the New York Mets and the Florida Marlins during their Opening Day game at Citi Field on April 5, 2010 in the Flushing neig
    Chris McGrath/Getty Images

    For as much as one would expect the Yankees to have many top-10 picks here, Pavano wraps up the list for them. The Dodgers, on the other hand, have three in the top eight.

    The first, and perhaps the most well-known of the three, is Mets phenom Darryl Strawberry. He made seven straight All-Star appearances for the Mets, and the Dodgers signed him to a five-year, $22.25 million contract.

    He played well his first season, but after that he played 43 and 32 games in two straight seasons, respectively, and the Dodgers cut their losses and released him.

7. Bruce Sutter, Atlanta Braves

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    COOPERSTOWN, NY - JULY 30:  2006 inductee Bruce Sutter gives his acceptance speech at Clark Sports Center during the Baseball Hall of Fame induction ceremony on July 30, 2006 in Cooperstown, New York.  (Photo by Jim McIsaac/Getty Images)
    Jim McIsaac/Getty Images

    It seemed like a good idea at the time to acquire the only current Hall of Famer on the list. Bruce Sutter was one of the best relievers in the game for the Cubs and Cardinals. The Atlanta Braves signed him to a six year, $10 million contract. They ended up with a pitcher who pitched 112 games but had an ERA over 4.50. He pitched in 1985 and 1986, was hurt for the entirety of 1987 and retired at the end of the 1988 season.

6. Andruw Jones, Los Angeles Dodgers

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    LOS ANGELES, CA - JULY 25:  Andruw Jones #25 of the Los Angeles Dodgers at bat against the Washington Nationals at Dodger Stadium on July 25, 2008 in Los Angeles, California.  (Photo by Lisa Blumenfeld/Getty Images)
    Lisa Blumenfeld/Getty Images

    Jones was coming off a 2007 season in which he hit .222 and was showing clear signs of slowing down. So, what do the Dodgers do? Sign him to a two-year deal worth $36.2 million. They got a .158 average in 75 games for their troubles. Not 33, I can't see Jones remaining in the game much longer.

5. Denny Neagle, Colorado Rockies

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    SAN FRANCISCO - JULY 20:  Starting pitcher Denny Neagle #15 of the Colorado Rockies delivers a pitch during the National League game against the San Francisco Giants at Pacific Bell Park on July 20, 2003 in San Francisco, California.  The Giants defeated
    Justin Sullivan/Getty Images

    In a move that the Rockies had absolutely no business making, they signed Neagle to a $51 million, five-year contract. He had just come off a Yankees stint with a .500 record and 5.81 ERA, and fared no better with the Rockies. He lasted half of his deal, and finished his time in Colorado with a 19-23 record and 5.57 ERA.

4. Albert Belle, Baltimore Orioles

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    4 Jul 2000: Albert Belle #88 of the Baltimore Orioles swings at the pitch during the game against the New York Yankees at Yankee Stadium in New York, New York.  The Orioles defeated the Yankees 7-6.Mandatory Credit: Jamie Squire  /Allsport
    Jamie Squire/Getty Images

    Maybe this is a bit high, but no one likes Albert Belle, so I don't have to worry. After very productive but difficult years with the Indians and White Sox, the Baltimore Orioles signed Belle to a five-year, $65 million contract. He had two fairly productive seasons, then...nothing. The Orioles shut him down and he retired due to hip issues. Belle is not the kind of player to sign to a long-term deal.

3. Jason Schmidt, Los Angeles Dodgers

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    LOS ANGELES, CA - AUGUST 5: Jason Schmidt #29 of the Los Angeles Dodgers reacts after hitting Craig Counsell #30 of the Milwaukee Brewers in the fourth inning at Dodger Stadium August 5, 2009 in Los Angeles, California.  (Photo by Harry How/Getty Images)
    Harry How/Getty Images

    Why, Dodgers? Nothing seems to work for them, as evidenced here. Signing a guy to a three-year, $47 million contract sounds nice when he's pitching fairly well, as Schmidt was.

    However, when the free agent ends up pitching 10 games and winning three, suddenly that's an all-time bust. That's over $15 million per win, nearly $5 million per appearance for Schmidt.

2. Wayne Garland, Cleveland Indians

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    The original free agent bust. Garland won 20 games in 1976, and was the big target in the first year of free agency. The Cleveland Indians signed him to a 10-year, $2.3 million deal. All for, until 1976, an unproven pitcher.

    He had an okay first year, but led the league in losses. Why was he struggling? He tore his rotator cuff in spring training, and his next four years were all disasters. He retired after the 1981 season, finishing only half his contract.

1. Mike Hampton, Colroado Rockies

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    KISSIMMEE, FL - MARCH 8:  Pitcher Mike Hampton #32 of the Atlanta Braves delivers against New York Yankees during a Spring Training game on March 8, 2005 at Cracker Jack Stadium at Disney's Wide World of Sports in Kissimmee, Florida.    (Photo by Rick Ste
    Rick Stewart/Getty Images

    Mike Hampton is the epitome of the free agent bust, so much so that multiple teams have felt the effects of a single bad contract. Hampton had an outstanding year with the Astros in 1999, and a very good year with the Mets in 2000. When he entered free agency, the Colorado Rockies jumped at the opportunity and offered him an eight-year deal worth $121 million.

    Hampton pitched poorly in two seasons with Colorado, and he was traded to the Florida Marlins. The Marlins immediately traded him to the Atlanta Braves without letting him pitch a game. He had a couple decent seasons for Atlanta, and then struggled in 2005 before missing 2006 and 2007. After one more lackluster year in 2008, all involved rejoiced at the conclusion of his contract.


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