MLB Free Agents 2012: All 30 Teams' Worst Signings in Franchise History

Doug Mead@@Sports_A_HolicCorrespondent IOctober 21, 2011

MLB Free Agents 2012: All 30 Teams' Worst Signings in Franchise History

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    As the 2011 World Series reaches its conclusion sometime in the next week to 10 days, the general managers of all 30 MLB teams will get to work on what is essentially their season in baseball—the offseason.

    While players will take time off to spend with their families and wind down from an exhausting seven to eight months of baseball, the GMs will be busy preparing their teams for the upcoming season. They go to work identifying team needs, and then addressing those needs via trades or free-agent signings.

    Every GM signs a player with the thought that each player signed will bring back value in the form of production. However at times, not every signing turns out that way. In fact, some signings have saddled teams with outrageous contracts for practically nothing back in return whatsoever.

    So, as the GMs get to work, we will get to work as well, identifying the one big signing for every single franchise that was without a doubt their worst signing in team history.

    Let’s get started…

Arizona Diamondbacks: Russ Ortiz

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    On December 11, 2004, the Arizona Diamondbacks announced that they had signed starting pitcher Russ Ortiz to a four-year, $33 million contract. The signing made perfect sense at the time; Ortiz was coming off two years in which he won 36 games for the Atlanta Braves, and in 2002 was instrumental in helping the San Francisco Giants get to the World Series before losing to the Anaheim Angels.

    However, within 18 months, Ortiz was sent packing by the D-Backs, sent out of town on a rail. Ortiz was woeful in his time in Phoenix, compiling a 5-16 record, a 7.00 ERA, 1.896 WHIP and an 11.4 hits-per-nine-innings ratio during his brief time in the desert.

    After winning 103 games in his first seven seasons, Ortiz won only 10 games in the next six years.

Atlanta Braves: Kenshin Kawakami

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    When the Atlanta Braves announced the signing of Japanese pitcher Kenshin Kawakami on January 13, 2009 for three years and $23 million, it was their first signing of a Japanese-born player ever in team history. Considering the results, they probably fired their Asian scout team.

    Kawakami came to the West with a more than impressive resume—he pitched 257 games (214 starts) for the Chunichi Dragons in Japan’s Central League, posting a 112-72 (.609) record with a 3.22 ERA. He notched 1,328 strikeouts and allowed just 351 walks in 1,642.1 innings of work for the Dragons. Kawakami also won Japan’s version of the Cy Young Award in 2004.

    However, Kawakami left his A-game in Japan. In two major league seasons, Kawakami was 8-22 with a 4.32 ERA, and never even made the Braves’ 25-man roster in 2011, earning his $6.7 million salary in Double-A ball and hurting his shoulder in the process.

    The Braves’ first Asian investment cost them $3 million per win.

    Honorable mention: Vinny Castilla (two years, $8 million)

Baltimore Orioles: Albert Belle

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    Following the 1998 season, Albert Belle, then a member of the Chicago White Sox and in the middle of a five-year, $55 million deal, invoked an unusual clause in his contract, allowing him to demand that he would remain one of the three highest-paid players in baseball. The White Sox refused to offer him more money, immediately making Belle a free agent again.

    The Baltimore Orioles and owner Peter Angelos obliged Belle, signing him to a five-year, $65 million contract, one of the largest contracts ever in baseball at that time. The Orioles also passed on signing slugger Rafael Palmeiro, who had just completed three of the most productive seasons of his career at that time in Baltimore, moving on to the Texas Rangers where he continued his hitting mastery.

    Belle was productive for two seasons with the O’s, hitting 60 HR with 220 RBI. However, due to a degenerative hip condition, Belle was forced to retire after the 2000 season and the Orioles had to keep a spot open on their 40-man roster just to recoup a portion of what they lost.

Boston Red Sox: Edgar Renteria

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    When the Boston Red Sox signed shortstop Edgar Renteria to a four-year, $40 million contract on December 19, 2004, they were hoping to get the player who was a two-time Gold Glove Award winner, two-time Silver Slugger winner and two-time All-Star with the St. Louis Cardinals.

    What they got instead was a player who struck out a career-high 100 times, committed a career-high 30 errors, a constant critique of the Fenway Park infield condition and a player who just never quite felt comfortable.

    The Sox shipped Renteria off to the Atlanta Braves for minor league prospect Andy Marte and $8 million in cash, along with an agreement to pay off the $3 million buyout on Renteria’s option year on his contract for the 2009.

    The Red Sox ended up paying $21 million for one season of a disgruntled Renteria. Nice.

    Honorable mentions: Julio Lugo (four years, $36 million), Matt Young (three years, $6.4 million)

Chicago Cubs: Milton Bradley

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    On January 9, 2009, the Chicago Cubs, looking for more production in their outfield, signed Milton Bradley to a three-year, $30 million contract.

    Cubs GM Jim Hendry took a chance on the surly outfielder, who had already worn out his welcome with six previous teams. However, Bradley told the Cubs faithful that he had been “misunderstood,” and could and would be a good guy for the North Siders.

    Bradley spent one tumultuous season with the Cubs, contributing a .257 average, 12 HR and 40 RBI along with numerous confrontations with manager Lou Piniella.

    On September 20, 2009, Bradley was suspended from the Cubs for the remainder of the season for violating team policy, and was dealt to the Seattle Mariners three months later for Carlos Silva and cash.

    Honorable mentions: Alfonso Soriano (eight years, $136 million), Kosuke Fukudome (four years, $48 million)

Chicago White Sox: Jaime Navarro

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    On December 11, 1996, the Chicago White Sox announced the signing of starting pitcher Jaime Navarro to a four-year, $20 million contract. Navarro was coming off two fairly productive seasons for the North Side rival Cubs, winning 29 games in two seasons with a 3.62 ERA.

    What the White Sox got was a pitcher who suddenly couldn’t put the ball over the plate. Navarro’s WHIP during three seasons on the South Side was a whopping 1.692, and he gave up over 100 earned runs in each of his three full seasons.

    The White Sox finally unloaded Navarro in January 2000, trading him to the Milwaukee Brewers for Cal Eldred and Jose Valentin. But the damage had already been done.

Cincinnati Reds: Eric Milton

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    It’s amazing in baseball in how a player who records one good season can then get rewarded with money they had never possibly have dreamed of making. That was certainly the case for former Cincinnati Reds pitcher Eric Milton.

    After one season with the Philadelphia Phillies in which he won 14 games with a 4.75 ERA, the Cincinnati Reds rewarded Milton with a three-year, $25.5 million contract in December 2004.

    Milton’s first year with the Reds was, in a word, disastrous. He gave up 40 home runs, allowed a whopping 237 hits in 183.1 innings, and posted an 8-15 record and 6.47 ERA.

    The 2006 season was only marginally better, with an 8-8 record and 5.19 ERA. The Reds finally gave up on Milton the following season, releasing him after six starts and a 5.17 ERA.

Cleveland Indians: Wayne Garland

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    When free agency was new in 1976, teams in MLB had no idea how to approach the new way of doing things, as they had no real examples to go by.

    In 1976, pitcher Wayne Garland won 20 games for the Baltimore Orioles in his first full season as a starter, making $19,000 for his efforts. The Cleveland Indians came calling, offering Garland a 10-year, $2.3 million contract, a whopping 12 times over his 1976 salary.

    Garland readily accepted, and proceeded to win just 28 games in the following five seasons. In Mar. 1977 while in spring training, Garland tweaked his shoulder during a Grapefruit League start, but gamely held on throughout the season, eventually losing a league-leading 19 games. Garland made only 20 starts over the next two seasons, trying to rehab his shoulder during the process.

    The Indians finally gave up on Garland following the 1981 season after another injury-plagued season.

Colorado Rockies: Mike Hampton

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    Southpaw pitcher Mike Hampton had a breakout season in 1999, winning 22 games for the Houston Astros and finishing runner-up in the voting for the National League Cy Young Award. After winning 15 games with an impressive 3.17 ERA in 2000 for the New York Mets, the Colorado Rockies came calling, offering Hampton an eight-year, $121 million contract in Dec. 2000 that Hampton readily accepted, making him one of the highest-paid pitchers at the time.

    However, the rarified air in Colorado did Hampton absolutely no good, posting a 21-28 record and 5.75 ERA for the Rockies in two seasons before being traded to the Florida Marlins along with Juan Pierre and cash for Vic Darensbourg, Charles Johnson, Pablo Ozuna and Preston Wilson.

    Two days later, the Marlins flipped Hampton to the Atlanta Braves along with cash for Ryan Baker and Tim Spooneybarger. The Rockies did save about $40 million in being able to dump Hampton’s contract, however it was still without a doubt the worst signing in club history.

Detroit Tigers: Carlos Guillen

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    Detroit Tigers second baseman Carlos Guillen had a productive first four years with the team, and was rewarded at the end of the 2007 season with a four-year, $48 million contract for his efforts.

    Since then, Guillen has largely been injury-prone, never playing in more than 113 games in any one season and only suiting up for 28 games in 2011.

    Hard to justify that kind of money for a guy who played fewer than half the games during the life of the contract.

    Honorable mention: Bobby Higginson (five years, $35 million)

Florida Marlins: John Buck

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    After a career year with the Toronto Blue Jays in which he hit 20 home runs with a .281 average, catcher John Buck was signed to a three-year, $18 million contract by the Florida Marlins, an usual contract given the Marlins’ penchant in recent years for avoiding long-term deals.

    Buck’s first year in South Florida was underwhelming at best. While Buck proved durable, playing in a career-high 140 games, he hit just .227 while striking out a career-high 115 times.

Houston Astros: Greg Swindell

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    When Drayton McLane first came on board as owner of the Houston Astros, he wanted to make a splash and he did so, approving the signing of starting pitcher Greg Swindell to a four-year, $16.4 million contract.

    Swindell was coming off a quality year with the Cincinnati Reds in 1992, winning 12 games with a 2.70 ERA.

    However, in three-plus years with the Astros, Swindell won 30 games with a 4.48 ERA and an overall WAR value of -0.5. By comparison, Swindell had compiled an overall 15.6 WAR in his seven seasons with the Cleveland Indians.

Kansas City Royals: Mark Davis

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    In 1989, the San Diego Padres had a record of 89-73 and their closer, Mark Davis, saved almost half of their games, collecting 44 that season and winning the NL Cy Young Award.

    The following year, Davis was with the Kansas City Royals after being rewarded with a three-year, $14 million contract, the largest contract in baseball at the time.

    The only problem was Davis completely lost his ability to throw strikes upon donning a Royals uniform. As it turned out, the 1989 season, the year before Davis signed his lucrative contract, turned out to be his last good year in the majors.

    By the time Davis’ Royals career was over after two-plus seasons, he contributed seven total with a 5.31 ERA and 1.71 WHIP.

Los Angeles Angels: Gary Matthews Jr.

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    After putting together a career year with the Texas Rangers in 2006 (.313 AVG, 19 HR, 79 RBI), the Los Angeles Angels came calling, signing Matthews Jr. to a five-year, $50 million contract.

    The signing turned into a complete disaster for the Angels. While Matthews Jr. had an okay first season in Anaheim (.252, 18 HR, 72 RBI), by the time 2009 rolled around, Matthews Jr. was essentially a fifth outfielder for the Angels, unable to provide any consistent production whatsoever.

    The Angels were finally able to get Matthews out of town, shipping him to the New York Mets in January 2010, however they were still paying for most of the remainder of his contract for the next two seasons.

Los Angeles Dodgers: Manny Ramirez

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    In March 2009, the Los Angeles Dodgers and slugger Manny Ramirez agreed to a two-year, $45 million contract. The Dodgers were thrilled with Manny, who helped the Dodgers reach the 2008 NLCS before losing to the Philadelphia Phillies.

    However, the contract was literally cursed from the start. Manny tested positive for a banned substance, causing him to miss 50 games in the 2009 season. An assortment of injuries saddled Manny in 2010, and the Dodgers finally had enough, placing him on waivers in August 2010 to be claimed by the Chicago White Sox.

    In Jun. of this year, Manny was listed as one of the largest creditors in the Dodgers’ bankruptcy documents, as he was still owed $21 million by the embattled franchise.

Milwaukee Brewers: Jeff Suppan

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    In 2006, the Milwaukee Brewers gave pitcher Jeff Suppan an early Christmas present, signing him to a four-year, $42 million contract on Christmas Eve. However it was the Brewers who ended up getting Scrooged.

    Suppan had three very successful seasons with the St. Louis Cardinals, with a record of 44-26 and a 3.95 ERA. However with the Brewers, Suppan was 29-36 with a 5.08 ERA, finally being released by Milwaukee in June 2010.

Minnesota Twins: Tsuyoshi Nishioka

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    The Minnesota Twins have always been a fiscally responsible team, much preferring to develop homegrown talent and make prudent trades rather than relying on the free-agent market.

    That’s why their signing of second baseman/shortstop Tsuyoshi Nishioka was so puzzling, and if the 2011 season is any example, obviously not a great decision.

    Nishioka was signed to a three-year, $9.25 million contract in January, purchasing him from the Chiba Lotte Marines of the Japan Pacific League.

    Nishioka was hurt for much of the year, appearing in only 68 games with a .226 batting average. And apparently, he never learned how to run in Japan, either. In six stolen base attempts, Nishioka was caught stealing four times.

New York Mets: Oliver Perez

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    The New York Mets have certainly had their share of bad signings, but this particular one was just puzzling from the start.

    Starting pitcher Oliver Perez was coming off a so-so season for the Mets in 2008, with a 10-7 record and 4.22 ERA, and the Mets saw fit to offer Perez a three-year, $36 million contract.

    Over the next two seasons, Perez was 3-9 with a 6.81 ERA in 21 total starts. Perez didn’t even make it to the last year of his contract in 2011, being released on March 23. The Mets ate the last $12 million of his contract.

    Honorable mention: Bobby Bonilla (five years, $25 million)

New York Yankees: Kei Igawa

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    When the New York Yankees lost out on the bidding rights to Japanese pitcher Daisuke Matsuzaka in late 2006, they went with their second option—fellow Japanese import Kei Igawa.

    The Yankees paid $26 million for the right to negotiate exclusively with Igawa, and then offered him a five-year, $20 million contract. During those five years, Igawa won exactly two games, meaning the Yankees paid $23 million per win.

    Somehow, that doesn’t seem like a really good foreign exchange rate.

    Honorable mention: Carl Pavano (four years, $40 million)

Oakland Athletics: Esteban Loaiza

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    The Oakland Athletics general manager has rarely inked players to long-term lucrative deals in Oakland, preferring to take chances on smaller deals with a low-risk/high-reward factor. So when he signed pitcher Esteban Loaiza to a three-year, $21 million deal in November 2005, eyes were certainly raised.

    Turns out that Beane should have stuck to his normal modus operandi.

    After posting an 11-9 record and 4.89 ERA in the 2006 season for the A’s, injuries completely sapped Loaiza of whatever he may have had left in the tank, and Beane released Loaiza in August 2007.

Philadelphia Phillies: Adam Eaton

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    The Philadelphia Phillies starting pitcher actually won a World Series ring in 2008, but he did it while watching his Phillies on television from his home.

    The Phillies signed Eaton to a three-year, $24 million contract in late 2006, and in two years, Eaton won 14 games with an ERA south of 6.00. During those two seasons, Eaton was never added to the postseason roster, and he was released before the 2009 season began, with the Phillies eating the final $9 million of his contract.

    But, Eaton has a ring.

Pittsburgh Pirates: Derek Bell

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    The outfielder had enjoyed a serviceable career in the majors before arriving in Pittsburgh, enjoying some years of productivity while with the Houston Astros in the mid-1990s, twice driving in over 100 runs in a season.

    Pittsburgh Pirates GM Cam Bonifay offered Bell a two-year, $9.75 million in late 2000, a deal that he readily accepted. And the Pirates readily kicked Bonifay out the door some months later, with the Bell deal likely being the last straw.

    Bell played exactly 46 games for the Pirates in 2001, landing on the disabled list twice and hitting a robust .173.

    Bell was released the following spring training by new GM Dave Littlefield, and Bell’s cantankerous attitude and questionable play were gone, with Littlefield and the Pirates swindled out of the remaining $4.9 million of Bell’s contract.

    Bell never played again in the majors.

San Diego Padres: Oscar Gamble

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    Coming off a failed campaign in 1976 with the New York Yankees, outfielder Oscar Gamble redeemed himself in 1977 with the Chicago White Sox, putting up career-high numbers with a .297 average, 31 HR and 83 RBI.

    The San Diego thought enough of Gamble’s career year to offer him a six-year, $2.85 million contract. Gamble’s career in San Diego was practically over before it started, lasting just one year and hitting just seven home runs. Less than a month after the season ended, Gamble with shipped off to the Texas Rangers in a five-player trade.

San Francisco Giants: Barry Zito

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    This may actually qualify as the worst free-agent signing in history.

    After a stellar career in which he won the American League Cy Young Award in 2002, Barry Zito signed a seven-year, $126 million contract with the San Francisco Giants.

    To say the Giants got hosed would be putting it mildly.

    Thus far in five seasons, Zito is 43-61 with a 4.55 ERA, and was left off the Giants postseason roster as they captured their first World Series Championship in 56 years in 2010.

    The Giants are on the hook for an additional two years and $46 million.

Seattle Mariners: Carlos Silva

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    What were the Seattle Mariners thinking?

    After posting two losing seasons in a row for the Minnesota Twins, starting pitcher Carlos Silva was given a four-year, $48 million contract by the Seattle Mariners.

    And I mean given to him, because he certainly didn’t earn it.

    Turns out he didn’t earn the money with the Mariners either, winning just five games in two seasons before being shipped off to the Chicago Cubs with cash for mercurial outfielder Milton Bradley in December 2009.

St. Louis Cardinals: Kyle Lohse

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    When St. Louis Cardinals starting pitcher Kyle Lohse signed a $4.25 million one-year contract in March 2008, he proceeded to have a career year, posting a 15-6 record and 3.78 ERA. The Cardinals were so impressed that they then offered Lohse a four-year, $41 million deal.

    Lohse won exactly 10 games in the first two years of that contract before finally rebounding this year with a 14-8 record.

    Lohse has lost both of his starts thus far in the 2011 postseason, so someone is really going to have to explain to me how his contract was ever justified.

Tampa Bay Rays: Manny Ramirez

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    This one wins by default.

    After two tumultuous years in Los Angeles with the Dodgers, and taking $45 million of their money, Manny Ramirez signed with the Tampa Bay Rays for one year at $2 million for the 2011 season.

    We all know how well that deal worked out.

Texas Rangers: Alex Rodriguez

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    When Texas Rangers owner Tom Hicks signed Alex Rodriguez to a 10-year, $252 million contract before the 2001 season, no one questioned A-Rod’s talent in any way.

    Rodriguez’s three years in Texas were indeed productive, hitting a career-high 57 home runs in 2002 and winning the AL MVP Award a year later, becoming only the second player in history to win an MVP Award with a last-place team (Andre Dawson).

    Keep that in mind here—I said LAST-PLACE Texas Rangers. When you are paid a contract that is easily the highest in baseball, it’s generally expected that you would lift your team out of the cellar.

    The Rangers were rid of A-Rod when they dealt him to the New York Yankees in February 2004, eventually paying the Yankees an additional $67 million for A-Rod’s contract.

Toronto Blue Jays: Vernon Wells

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    When the Toronto Blue Jays signed center fielder Vernon Wells to a seven-year, $126 million contract in late 2007, just about everyone in baseball thought one thing—OVERPAID!

    New general manager Alex Anthopoulos obviously thought so as well, dealing Wells to the Los Angeles Angels in January 2011 for Juan Rivera and Mike Napoli. The Angels were then stuck with the remaining four years and $84 million.

    We all see how well that deal has worked out thus far, right?

Washington Nationals: Jayson Werth

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    Speaking of overpaid...

    The Washington Nationals wanted to make a splash this past offseason, especially after losing Adam Dunn to the Chicago White Sox. They went out and offered Philadelphia Phillies right fielder Jayson Werth a seven-year, $126 million contract.

    Werth hit .232 with 20 HR and 58 RBI in the 2011, easily his lowest production since the 2007 season.

    That comes nowhere near justifying a nine-figure contract.


    Doug Mead is a featured columnist with Bleacher Report. His work has been featured on the Seattle Post-Intelligencer, SF Gate, CBS Sports, the Los Angeles Times and the Houston Chronicle. Follow Doug on Twitter, @Sports_A_Holic.