Every MLB Team's Worst Free-Agent Signing of the 2000s

Joel Reuter@JoelReuterBRFeatured Columnist

Every MLB Team's Worst Free-Agent Signing of the 2000s

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    Brian Bahr/Getty Images

    Not every MLB free agency signing plays out as hoped.

    On Tuesday, we selected every MLB team's best free-agent signing of the 2000s, and now it's time for the opposite end of the spectrum.

    From the Colorado Rockies shelling out nine figures to sign Mike Hampton to the Chicago Cubs dismissing Milton Bradley from the team before his first year on the North Side came to a close, each team has at least one memorable free agency flop during the 2000s.

    To clarify, the 2000s in the context of this article refer to the decade running from 2000 through 2009.

    There were no strict parameters for inclusion, though we did try to avoid including one-year deals whenever possible. That said, some teams simply were not active enough for there to be any impactful multiyear contracts, and in those cases a one-year deal wound up being the pick.

    Let's get started!

AL East

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    Carl Pavano
    Carl PavanoFRANK FRANKLIN II/Associated Press

    Baltimore Orioles: RP Danys Baez—Three years, $19 million

    An All-Star with Tampa Bay in 2005 when he racked up 41 saves and had a 2.86 ERA in 67 appearances, Baez was signed in 2007 to bolster an Orioles bullpen that ranked 29th in the majors with a 5.27 ERA the year before. He had a 6.44 ERA in 53 games his first year in Baltimore, then missed the entire second season of his contract recovering from Tommy John surgery.


    Boston Red Sox: SS Edgar Renteria—Four years, $40 million

    A three-time All-Star and two-way standout during his six seasons in St. Louis, Renteria was supposed to plug the hole Nomar Garciaparra left behind at shortstop. Instead, he posted a middling 89 OPS+ and 1.4 WAR in the first year of his deal before he was traded to Atlanta for prospect Andy Marte. An All-Star selection during his first season with the Braves was salt in the wound.


    New York Yankees: SP Carl PavanoFour years, $39.95 million

    Following a sixth-place finish in NL Cy Young voting in 2004, Pavano hit free agency at the perfect time. He ended up making just 26 starts during his four seasons in pinstripes, struggling to a 5.00 ERA and 1.46 WHIP in 145.2 innings when he was healthy enough to take the mound. Japanese League standout Kei Igawa (5/$46M in 2006) is also a strong candidate for the title of worst Yankees signing.


    Tampa Bay Rays: DH Pat BurrellTwo years, $16 million

    Fresh off a 33-homer season for the World Series champion Philadelphia Phillies, Burrell joined a Rays team in serious need of some middle-of-the-order thump. He hit just .221 with an 85 OPS+ and 14 home runs in the first year of his contract, and he was designated for assignment the following May. He caught on with the San Francisco Giants a few days later and logged a 136 OPS+ with 18 home runs in 96 games the rest of the way.


    Toronto Blue Jays: RP B.J. RyanFive years, $47 million

    Ryan had a dominant first season with the Blue Jays, converting 38 of 42 save chances with a 1.37 ERA to earn his second successive All-Star selection. After an injury-plagued 2007 in which he made just five appearances, he was solid again in 2008 with 32 saves and a 2.95 ERA, but that was the end of his productivity. Still on the hook for roughly $15 million, the Blue Jays released him midway through the fourth year of his contract with a 6.53 ERA in 25 appearances.

AL Central

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    Kerry Wood
    Kerry WoodMark Duncan/Associated Press

    Chicago White Sox: SP Orlando Hernandez—Two years, $8 million

    "El Duque" went 8-2 with a 3.30 ERA in 15 starts in 2004, and the 38-year-old managed to parlay that into a multiyear deal with the White Sox. He struggled to a 5.12 ERA in 128.1 innings in '05, though he did toss four shutout innings in the postseason, and the White Sox cut their losses that offseason. He was traded to Arizona in exchange for Javier Vazquez, with the South Siders also parting with future All-Star center fielder Chris Young in that deal.


    Cleveland Guardians: RP Kerry Wood—Two years, $20.5 million

    After resurrecting his career as a closer in 2008 with 34 saves and a 3.26 ERA in 65 games, Wood hit the open market for the first time in his career. Cleveland rolled the dice on his second act with a two-year deal, but he converted just 28 of 37 save chances with a 4.80 ERA in 81 games before he was flipped to the Yankees for two players to be named (Andrew Shive and Matt Cusick) midway through his second year.


    Detroit Tigers: 3B Craig Paquette—Two years, $5 million

    After slugging 40 home runs in three seasons as a utility player with the Cardinals, Paquette was given an opportunity to be an everyday third baseman. However, it was not long before he found himself back on the bench. In his two years with the team, he hit a paltry .189/.215/.288 for a 37 OPS+ with four home runs and 20 RBI in 299 plate appearances.


    Kansas City Royals: RF Jose GuillenThree years, $36 million

    After posting a 116 OPS+ with 23 home runs and 99 RBI with the Mariners in 2007, Guillen was one of the top power bats on the market, though there was also a reason he had played for eight teams in 11 seasons. He hit .256 with a .308 on-base percentage and 94 OPS+ during his time with the Royals, tallying minus-2.3 WAR in 340 games.


    Minnesota Twins: DH Rondell White—Two years, $8.5 million

    The Twins hoped a full-time move to DH would help the oft-injured White stay healthy long enough to tap into the potential that had once made him a rising star with the Montreal Expos. Alas, he played in only 137 games in two years, hitting .229/.266/.354 for a 62 OPS+ with 11 home runs and 58 RBI.

AL West

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    Gary Matthews Jr.
    Gary Matthews Jr.CHRIS CARLSON/Associated Press

    Houston Astros: SP Woody Williams—Two years, $12.5 million

    Williams went 12-5 with a 3.65 ERA in 145.1 innings with the San Diego Padres in 2006, and that was enough for him to secure a multiyear deal entering his age-40 season. The veteran right-hander went 8-15 with a 5.27 ERA in 188 innings in the first year of his contract, and the Astros released him right before Opening Day the following season.


    Los Angeles Angels: CF Gary Matthews Jr.Five years, $50 million

    A career journeyman before he found an everyday role with the Texas Rangers, Matthews hit .313/.371/.495 for a 121 OPS+ with 69 extra-base hits and 5.2 WAR in his contract year. He had an 18-homer, 72-RBI season in his first year with the Angels, but his production plummeted from there. He was worth minus-1.1 WAR over the next two years before he was traded to the New York Mets in a salary dump.


    Oakland Athletics: SP Esteban LoaizaThree years, $21.4 million

    Loaiza broke out after his 30th birthday, turning in a 21-win season in 2003 when he started the All-Star Game. His ERA spiked the following year, but he bounced back with the Washington Nationals in 2005, and the small-market Athletics made a significant investment. He had a 4.62 ERA in 28 starts in Oakland before he was claimed by the Los Angeles Dodgers in an August waiver deal.


    Seattle Mariners: SP Carlos Silva—Four years, $48 million

    With a 4.31 ERA and 102 ERA+ in 945 career innings, Silva was never more than a back-of-the-rotation innings eater, but the Mariners paid him like an ace. The burly right-hander went 5-18 with a 6.81 ERA in 183.2 innings in his first two seasons with the team before he was traded to the Chicago Cubs for Milton Bradley in a swap of bad contracts.


    Texas Rangers: SP Chan Ho ParkFive years, $65 million

    After eight seasons with the Dodgers, including back-to-back 200-strikeout seasons and an All-Star appearance in 2001, Park hit the open market for the first time in his career. He made 68 starts in parts of four seasons with the Rangers, struggling to a 5.79 ERA and 1.61 WHIP before he was traded to San Diego for aging slugger Phil Nevin.

NL East

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    Jason Bay
    Jason BayChristopher Pasatieri/Getty Images

    Atlanta Braves: SP Kenshin KawakamiThree years, $23 million

    Kawakami was already 33 years old with 11 years of experience in the Japanese League under his belt when he made his way stateside. After posting a solid 3.86 ERA in 156.1 innings as a rookie, he was demoted to the bullpen in his second year and he spent all of his final season at Double-A after being optioned to the minors.


    Miami Marlins: SP Al Leiter—One year, $8 million

    "This is a terrific reunion of Al [Leiter] and this franchise, and this is a big day for the Florida Marlins and South Florida," Marlins general manager Larry Beinfest told reporters.

    The left-hander was an All-Star in 1996 and a key contributor during the team's 1997 World Series run before he was traded to the New York Mets. After seven seasons, he returned to Florida, but his return didn't go as hoped as he struggled to a 6.64 ERA in 16 starts before he was sent to the Yankees.


    New York Mets: CF Jason Bay—Four years, $66 million

    In his only full season with the Boston Red Sox, Bay posted a 134 OPS+ with 36 home runs and 119 RBI to finish seventh in AL MVP voting and win Silver Slugger honors. The Mets signed him to replace Carlos Beltran's bat in the lineup, but he didn't produce as hoped, hitting .234/.318/.369 with 1.8 WAR in three seasons before he was released.


    Philadelphia Phillies: SP Adam Eaton—Three years, $24 million

    With a 5.12 ERA in 65 innings with the Texas Rangers in 2006, Eaton wasn't exactly coming off a career year when he entered free agency. That didn't stop the Phillies from giving him a three-year deal, and he was shelled to the tune of a 6.10 ERA in 268.2 innings over the first two seasons of his contract before he was outright released.


    Washington Nationals: SS Cristian GuzmanFour years, $16.8 million

    Guzman hit .219 with a 53 OPS+ and minus-1.4 WAR in his first season with the Nationals, then played just 46 games over the next two seasons while recovering from shoulder surgery, a hamstring injury, and a torn thumb ligament. He did hit .316/.345/.440 with 49 extra-base hits and 4.6 WAR in the final year of the contract, but that coaxed an ill-advised two-year deal out of the Nats.

NL Central

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    Milton Bradley
    Milton BradleyM. Spencer Green/Associated Press

    Chicago Cubs: RF Milton BradleyThree years, $30 million

    Bradley led the AL in on-base percentage (.436) and OPS+ (162) in 2008, and the Cubs penciled him into the No. 3 spot in the lineup after signing him that offseason. He produced a disappointing 100 OPS+ with 12 home runs in his first season on the North Side, and he became enough of an off-the-field distraction that he was dismissed from the team with 15 games remaining. He was flipped to Seattle for overpaid right-hander Carlos Silva after one year with the team.


    Cincinnati Reds: SP Eric Milton—Three years, $25 million

    Who would have guessed the pitcher who gave up an NL-high 43 home runs in 2004 would struggle pitching in Great American Ball Park? Milton served up another 40 long balls with a 6.47 ERA in 186.1 innings in his first year with the Reds, and he wrapped up his three-year contract with a 5.83 ERA and minus-3.5 WAR in 66 starts.


    Milwaukee Brewers: CF Jeffrey HammondsThree years, $21 million

    Hammonds hit an eye-popping .399/.465/.651 with 14 home runs and 65 RBI in 64 games at Coors Field in 2000. The Brewers chose to ignore the fact that his OPS was a staggering 375 points lower on the road, and it burned them. He hit .248/.321/.398 with minus-0.3 WAR in 187 games with the Brew Crew before he was released midway through his third year.


    Pittsburgh Pirates: RF Derek Bell—Two years, $9.75 million

    Bell hit .173 with five home runs in 46 games in his first year with the Pirates. Upon learning he would have to compete for the starting right field job the following spring, he went into what he dubbed "Operation Shutdown" and left the team on March 29. Two days later, he was released, and that was the end of his MLB career.


    St. Louis Cardinals: 1B Tino Martinez—Three years, $21 million

    Martinez had a 105 OPS+ and averaged 18 home runs and 72 RBI in his first two seasons in St. Louis. However, as Ryan Fagan of Sporting News noted, his propensity for speaking fondly of his time with the Yankees rubbed some fans the wrong way, and he was the rare home player greeted by boos at Busch Stadium. He was sent to the Rays in a salary dump prior to his third year.

NL West

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    Andruw Jones
    Andruw JonesLiz O. Baylen/Getty Images

    Arizona Diamondbacks: SP Russ OrtizFour years, $33 million

    Ortiz went 99-56 with a 3.93 ERA and 106 ERA+ while tossing at least 195 innings every season during the six-year span leading up to his free agency. However, the wheels immediately fell off in Arizona as he was knocked around to a 6.89 ERA in 115 innings in his D-backs debut. The struggles continued the following year and he was released in June with more than half of his contract remaining.


    Colorado Rockies: SP Mike HamptonEight years, $121 million

    The Rockies spent $172 million on Hampton and fellow left-hander Denny Neagle during the 2000-01 offseason, and both pitchers were epic flops. Hampton posted a 5.75 ERA and 88 ERA+ in 381.2 innings in his first two seasons before he was traded to the Marlins in a six-player deal that brought Preston Wilson to Colorado. The Marlins then flipped him to Atlanta, where he promptly enjoyed a career resurgence.


    Los Angeles Dodgers: CF Andruw JonesTwo years, $36.2 million

    It's truly a toss-up here between two of the worst contracts in baseball history:

    • Andruw Jones (2/$36.2M): 75 G, 35 OPS+, .158/.256/.249, -1.6 WAR
    • Jason Schmidt (3/$47M): 10 GS, 72 ERA+, 6.02 ERA, -0.9 WAR

    The Schmidt deal was longer, but the Jones deal had a higher annual value and he was released after one season at a cost of $21.4 million in dead money.


    San Diego Padres: 2B Marcus GilesOne year, $3.75 million

    One of baseball's best offensive second basemen at his peak, Giles had a down year in his final season with the Atlanta Braves as he tried to adjust to being a leadoff hitter. Still just 29 years old, he joined his brother in San Diego in free agency, but he hit just .229/.304/.317 for a 69 OPS+ with 0.0 WAR in 116 games in what was the final season of his MLB career.


    San Francisco Giants: SP Barry Zito—Seven years, $126 million

    There is still a pocket of Giants fans who will defend this as a good signing, largely based on 7.2 scoreless innings in Game 5 of the 2012 NLCS. Zito was durable, tossing 1,139.1 innings over the life of the contract, but a 4.62 ERA and 87 ERA+ is not what the Giants expected when they handed him what was at the time the largest contract in MLB history for a pitcher.


    All stats courtesy of Baseball Reference.