Top 3 Worst Free-Agent Signings in the History of Each MLB Franchise

Joel Reuter@JoelReuterBRFeatured ColumnistNovember 20, 2019

Top 3 Worst Free-Agent Signings in the History of Each MLB Franchise

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    Kei Igawa
    Kei IgawaKathy Willens/Associated Press

    There are varying levels of risk and reward with any free-agent signing, and even the best-laid plans can go off track for a variety of reasons. Whether it's a player missing time to injury, a late-career decline in production or something else entirely, some contracts end up becoming busts.

    With that in mind, we set out to identify the three worst free-agent signings in the history of each MLB franchise.

    With so many contracts to consider, the first step was to narrow the field by setting some parameters for inclusion. Those were as follows:

    • No contract extensions: Contract extensions and players re-signing with the same team in free agency were not considered for inclusion. That means you will not see Chris Davis among the Baltimore Orioles' worst signings since his albatross deal came with a team for which he already played.
    • No one-year deals: Signing someone to a one-year contract is a no-risk move, so ranking them alongside multiyear deals doesn't seem fair.

    To help provide some better context, alongside each player's contract information is a multiplier to show how his salary stacked up to the league-average figure over the course of the deal.

    Now that we're on the same page, let's get started.


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Arizona Diamondbacks

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    Russ Ortiz
    Russ OrtizMARK J. TERRILL/Associated Press

    No. 1: SP Russ OrtizDec. 11, 2004

    Terms: Four years, $33 million (3x league avg)

    After posting a 3.93 ERA while averaging 209 innings and 33 starts in the six seasons prior to reaching free agency, Ortiz turned in a brutal 6.89 ERA over 115 innings in his first year with the D-backs. He was released the following June with a 7.54 ERA through six starts.

          

    No. 2: OF Yasmany Tomas—Dec. 9, 2014

    Terms: Six years, $68.5 million (2.4x league avg)

    While he has shown some legitimate pop, including a 31-homer season in 2016, Tomas has proved unplayable defensively (minus-30 defensive runs saved) and has been relegated to the minors for much of the past three years. He's still owed $17 million in 2020 and has thus far been worth minus-2.5 wins above replacement over the life of his contract.

         

    No. 3: SP Willie Blair—Dec. 6, 1997

    Terms: Three years, $11.5 million (2.3x league avg)

    Blair went 16-8 with a 4.17 ERA in 175 innings during his contract year with the Detroit Tigers and earned himself a multiyear deal. He lasted just half a season in Arizona, struggling to a 5.34 ERA in 23 starts before he was flipped to the New York Mets in exchange for Bernard Gilkey's bloated contract.

Atlanta Braves

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    B.J. Upton
    B.J. UptonJohn Bazemore/Associated Press

    No. 1: OF B.J. UptonNov. 29, 2012

    Terms: Five years, $75.25 million (3.8x league avg)

    The Braves overlooked a .298 on-base percentage and 169 strikeouts and paid Upton handsomely for his 28-homer, 31-steal season in 2012. He lasted just two years in Atlanta, hitting .198 with a 66 OPS+ before he was attached to Craig Kimbrel and traded to the San Diego Padres.

          

    No. 2: RP Bruce SutterDec. 7, 1984

    Terms: Six years, $9.1 million (3.3x league avg)

    After he saved 23 games with a 4.48 ERA in the first season of his contract, recurring shoulder issues limited Sutter to just 54 more total appearances before he was released at the conclusion of the 1989 campaign. The Braves deferred a good chunk of the contract and are paying him $1.12 million annually over 30 years, a payout that lasts through the 2021 season, per Dan Lewis of The Athletic.

         

    No. 3: SP Kenshin KawakamiJan. 13, 2009

    Terms: Three years, $23 million (2.5x league avg)

    Kawakami already had 11 pro seasons under his belt in Japan when he made his way stateside for his age-34 campaign. After posting a solid 3.86 ERA over 156.1 innings as a rookie, he struggled to a 5.15 ERA in 87.1 frames the following season before spending the entire third year of the contract in the minors.

Baltimore Orioles

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    GAIL BURTON/Associated Press

    No. 1: OF Albert BelleDec. 1, 1998

    Terms: Five years, $65 million (6.3x league avg)

    This contract briefly made Belle the highest-paid player in baseball, and he lived up to that billing with a massive first season, posting a 143 OPS+ with 37 home runs and 117 RBI. However, his career ended prematurely following his second year in Baltimore due to a degenerative hip condition, though he remained on the 40-man roster for the duration of the contract as a condition of his insurance policy.

          

    No. 2: SP Ubaldo JimenezFeb. 19, 2014

    Terms: Four years, $48 million (2.9x league avg)

    A bounceback season with the Cleveland Indians in 2013 earned Jimenez a hefty payday from the pitching-needy Orioles, but he ended up creating more problems than he solved. Over the life of the contract, he pitched to a 5.22 ERA and 1.50 WHIP while averaging 26 starts and 149 innings.

         

    No. 3: RP Danys BaezNov. 27, 2006

    Terms: Three years, $19 million (2.2x league avg)

    Despite a 4.53 ERA in 57 appearances during the 2006 season, Baez received a lucrative three-year deal from the O's as they focused on bolstering a shaky bullpen. He was shelled in his first season with the team and missed all of 2008 recovering from Tommy John surgery, finishing out the contract with a 5.02 ERA over 112 appearances.

Boston Red Sox

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    Pablo Sandoval
    Pablo SandovalStephan Savoia/Associated Press

    No. 1: 3B Pablo SandovalNov. 25, 2014

    Terms: Five years, $95 million (4.4x league avg)

    Part of a spending spree that also included a four-year, $88 million deal for Hanley Ramirez, Sandoval hit .245 with a 75 OPS+ and 10 home runs in his first year, and that wound up being his best season in a Red Sox uniform. He played in just 35 more games over the next two years before he was released with minus-2.1 WAR to show for his time in Boston.

         

    No. 2: OF Rusney CastilloAug. 23, 2014

    Terms: Seven years, $72.5 million (2.3x league avg)

    Castillo went 12-for-36 in 10 games down the stretch in 2014, and he opened the next season as the No. 21 prospect in baseball, according to Baseball America. Alas, he hit just .253/.288/.359 over 289 plate appearances in 2015 during what would be his only extended MLB action. He's now playing out the contract in the minors after being outrighted off the 40-man roster.

          

    No. 3: OF Carl CrawfordDec. 11, 2010

    Terms: Seven years, $142 million (5.4x league avg)

    A dynamic player during his time in Tampa Bay, Crawford was anything but in Boston, posting a lifeless .260/.292/.419 line and 0.9 WAR in two seasons before he was traded to the Los Angeles Dodgers in an August blockbuster that also included Adrian Gonzalez and Josh Beckett.


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Chicago Cubs

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    Milton Bradley
    Milton BradleyJim Prisching/Associated Press

    No. 1: OF Milton BradleyJan. 9, 2009

    Terms: Three years, $30 million (3.3x league avg)

    After leading the American League in on-base percentage (.436) and OPS+ (162) during the 2008 season, Bradley tanked in what would be his lone season in Chicago. He had a ho-hum 100 OPS+ in 473 plate appearances and was a constant distraction in the clubhouse, eventually leading to his dismissal from the team with 15 games left on the schedule. He was then flipped to Seattle for Carlos Silva's bad contract during the offseason.

          

    No. 2: C Todd HundleyDec. 19, 2000

    Terms: Four years, $23.5 million (2.6x league avg)

    It looked like the Cubs finally had an offensive threat at the catcher position when Hundley was signed on the heels of back-to-back 24-homer seasons with the Los Angeles Dodgers. Alas, he hit a pitiful .199/.285/.398 for a 79 OPS+ in 579 plate appearances over the first two years of the deal before he was sent back to the Dodgers in exchange for Eric Karros and Mark Grudzielanek.

         

    No. 3: SP Edwin Jackson—Jan. 2, 2013

    Terms: Four years, $52 million (3.4x league avg)

    After missing out on signing Anibal Sanchez, the Cubs settled for the well-traveled Jackson in an effort to bolster the starting rotation. He had a 5.58 ERA in 58 starts over the first two seasons of the contract before he was moved to the bullpen, where he pitched adequately before his release in July. No one could have guessed at that time that he would still be active in 2019.

Chicago White Sox

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    Jaime Navarro
    Jaime NavarroDavid Seelig/Getty Images

    No. 1: SP Jaime NavarroDec. 11, 1996

    Terms: Four years, $20 million (3.2x league avg)

    Signed away from the crosstown Cubs, Navarro spent three seasons pitching batting practice on the South Side. He ran up a 6.06 ERA and 1.69 WHIP with an unsightly 11.6 hits per nine innings allowed and tossed 181 innings per season before he was traded to the Milwaukee Brewers in a deal that inexplicably brought back Jose Valentin and Cal Eldred.

          

    No. 2: DH Adam DunnDec. 3, 2010

    Terms: Four years, $56 million (4.2x league avg)

    After a rough first season, Dunn slugged 41 home runs while leading the AL in both walks (105) and strikeouts (222) and making the All-Star team in 2012. His production plummeted from there, and he finished his White Sox career with a .201 average, 32.9 percent strikeout rate and minus-0.9 WAR.

         

    No. 3: 1B Adam LaRoche—Nov. 25, 2014

    Terms: Two years, $25 million (3x league avg)

    LaRoche hit a disappointing .207/.293/.340 with 12 home runs in 2015, then he abruptly retired and walked away from the final $13 million of his contract. It was eventually revealed that his decision stemmed from complaints from several players about his son's "constant presence" in the locker room and subsequent requests from the team to limit his time in the clubhouse.

Cincinnati Reds

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    Eric Milton
    Eric MiltonTOM GANNAM/Associated Press

    No. 1: SP Eric Milton—Dec. 28, 2004

    Terms: Three years, $25 million (3.1x league avg)

    Milton led the NL in home runs allowed (43) and pitched to a mediocre 4.75 ERA over 201 innings with the Philadelphia Phillies in 2004, yet the Reds still gave him a three-year deal at more than three times the league-average salary. He was knocked around to the tune of a 5.89 ERA and 1.46 WHIP in his first two seasons, then he underwent Tommy John surgery early in the 2007 season.

          

    No. 2: RP Francisco Cordero—Nov. 28, 2007

    Terms: Four years, $46 million (3.8x league avg)

    While he saved 150 games during his four seasons with the Reds, earning an All-Star nod in 2009, Cordero also had 24 blown saves during that time. Pitching for a non-contending Reds team in three of those four seasons, he was more an expensive luxury than a key contributor.

             

    No. 3: OF Willy Taveras—Dec. 27, 2008

    Terms: Two years, $6.25 million (1x league avg)

    Taveras was signed to plug a glaring hole in center field after leading the NL with 68 steals during the 2008 season. Instead, he hit just .240 with a .275 on-base percentage and a brutal 48 OPS+ in 437 plate appearances, and he was traded to the Oakland Athletics during the offseason.

Cleveland Indians

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    Ron Kuntz Collection/Getty Images

    No. 1: SP Wayne GarlandNov. 19, 1976

    Terms: 10 years, $2.3 million (1x league avg)

    The first notable free-agent signing in Indians franchise history was a doozie. Garland went 20-7 with a 2.67 ERA and 1.24 WHIP for the Orioles before hitting free agency. After working a whopping 282.2 innings during his first year in Cleveland, he pitched just 330.2 total innings at a 5.28 ERA over the next four seasons before calling it a career.

          

    No. 2: 1B Keith HernandezDec. 7, 1989

    Terms: Two years, $3.5 million (2.4x league avg)

    At 36 years old and after hitting a punchless .233/.324/.326 with the New York Mets in 1989, Hernandez was little more than a name when the Indians brought him aboard. He hit .200 with a 49 OPS+ in 145 plate appearances in 1990 and then spent the entire 1991 season on the disabled list before retiring.

         

    No. 3: OF Nick SwisherJan. 3, 2013

    Terms: Four years, $56 million (3.7x league avg)

    During an offseason in which the Indians also gave Michael Bourn an ill-advised four-year, $48 million deal, Swisher turned out to be the biggest disappointment. After a productive first season, he hit just .208 with a 70 OPS+ in 2014, and he was wading below the .200 mark the following season before he was traded to the Braves in a salary dump.

Colorado Rockies

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    Brian Bahr/Getty Images

    No. 1: SP Mike HamptonDec. 12, 2000

    Terms: Eight years, $121 million (6x league avg)

    The Rockies went all-in on assembling a viable starting rotation during the 2000-01 offseason, and Hampton was the prized addition. Rather than pitching like an ace, he scuffled to a 5.75 ERA (88 ERA+) during his first two seasons in Colorado. The Rockies attached him to speedy outfielder Juan Pierre and traded him to the Marlins prior to the 2003 season in a deal that brought back Preston Wilson and Charles Johnson.

           

    No. 2: 1B/OF Ian DesmondDec. 13, 2016

    Terms: Five years, $70 million (3.4x league avg)

    This contract looked like a bad idea at the time. Three years in, it has been an unmitigated disaster. Desmond has been worth an unsightly minus-3.4 WAR thus far, due in part to his lack of a natural defensive home, and he's still owed $23 million over the next two years.

         

    No. 3: SP Denny Neagle—Dec. 4, 2000

    Terms: Five years, $51 million (4.4x league avg)

    Signed to be the Robin to Hampton's Batman, Neagle was similarly ineffective with a 5.57 ERA (91 ERA+) in 65 starts over the first three years of the contract. Elbow surgery sidelined him in 2004, and the final year of his contract was voided due to a violation of a morals clause.

Detroit Tigers

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    Jordan Zimmermann
    Jordan ZimmermannMark Cunningham/Getty Images

    No. 1: SP Jordan ZimmermannNov. 30, 2015

    Terms: Five years, $110 million (4.8x league avg)

    During his final four seasons with the Washington Nationals, Zimmermann posted a 3.13 ERA and 1.13 WHIP while averaging 32 starts and 203 innings pitched. Compare that to his first four seasons in Detroit, where he has a 5.61 ERA and 1.43 WHIP while averaging 24 starts and 127 innings, and he's earned the No. 1 spot here.

          

    No. 2: SP Mike Moore—Dec. 9, 1992

    Terms: Three years, $10 million (3x league avg)

    After an impressive four-year run with the Oakland Athletics, Moore didn't have much left in the tank when he joined the Tigers for his age-33 campaign. He ate up some innings, averaging 167 per season during his three years with the team, but his 5.90 ERA and 1.61 WHIP left him well short of living up to his contract.

         

    No. 3: 3B Dean PalmerNov. 13, 1998

    Terms: Five years, $36 million (3.5x league avg)

    Palmer swatted 38 home runs and won the Silver Slugger during his first season with the Tigers, and he followed that up with a 29-homer, 102-RBI campaign in 2000. Injuries took a major toll from there, though, as he played just 87 games and hit .191/.286/.338 over the final three years of the contract.

Houston Astros

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    Greg Swindell
    Greg SwindellRon Vesely/Getty Images

    No. 1: SP Greg SwindellDec. 4, 1992

    Terms: Four years, $16.4 million (3.7x league avg)

    Expectations were high for the one-two punch of Greg Swindell and Doug Drabek when both pitchers were added to the Houston staff during the 1992-93 offseason. Unfortunately, neither lived up to expectations, with Swindell pitching to a lackluster 4.48 ERA (87 ERA+) in 84 starts before he was released on June 3, 1996. He went on to reinvent himself as a reliever and pitch six more seasons elsewhere.

          

    No. 2: SP Woody WilliamsNov. 24, 2006

    Terms: Two years, $12.5 million (2.2x league avg)

    File signing a 40-year-old journeyman starter to a two-year contract under "bad ideas." A resurgent performance with the San Diego Padres that included a 3.65 ERA in 145.1 innings provided enough optimism to warrant the multiyear pact, but Williams lasted just one season, struggling to a 5.27 ERA in 188 innings before he was released.

         

    No. 3: SP Jim Clancy—Dec. 16, 1988

    Terms: Three years, $3.4 million (1.7x league avg)

    Clancy spent the first 12 seasons of his career with the Toronto Blue Jays before joining the Astros for his age-33 season. With a career 103 ERA+ at the time of the signing, he was far from a frontline starter, and he wound up stumbling to a 5.02 ERA in 36 starts and 60 relief appearances spanning 278 innings.

Kansas City Royals

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    Mark Davis
    Mark DavisMitchell Layton/Getty Images

    No. 1: RP Mark DavisDec. 11, 1989

    Terms: Four years, $13 million (3.7x league avg)

    With his stock at an all-time high after winning National League Cy Young honors in 1989, Davis secured what was, at the time, the highest annual salary in baseball when he joined the Royals. He lasted two-and-a-half seasons in Kansas City, tallying just seven saves while pitching to a 5.31 ERA before he was traded to the Braves for 37-year-old reliever Juan Berenguer.

          

    No. 2: OF Jose Guillen—Dec. 4, 2007

    Terms: Three years, $36 million (4x league avg)

    With limited on-base abilities and a volatile temper, Guillen never came close to living up to his contract. He had a .308 on-base percentage and a 94 OPS+ with 45 home runs in 340 games for the Royals before he was traded to the San Francisco Giants midway through the 2010 season.

         

    No. 3: 2B Omar InfanteDec. 16, 2013

    Terms: Four years, $30.25 million (1.8x league avg)

    A useful player during his time with the Detroit Tigers and Atlanta Braves, Infante was one of the least productive hitters in baseball while suiting up for the Royals. He hit .238/.269/.328 for a 63 OPS+ in 1,179 plate appearances and earned minus-0.3 WAR before he was released in June during his third season with the team.

Los Angeles Angels

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    Josh Hamilton
    Josh HamiltonVictor Decolongon/Getty Images

    No. 1: OF Josh HamiltonDec. 15, 2012

    Terms: Five years, $125 million (6.3x league avg)

    Hamilton recorded a meager 2.8 WAR over his first two years in an Angels uniform before the team paid $68.4 million of the $74.4 million left on his contract to facilitate a trade with the Texas Rangers. That's a staggering sunk cost and a disaster of a signing.

          

    No. 2: OF Gary Matthews Jr.Nov. 22, 2006

    Terms: Five years, $50 million (3.4x league avg)

    After logging an 89 OPS+ over his first seven MLB seasons, Matthews broke out with a 121 OPS+ and 69 extra-base hits in a 5.2 WAR season with the Texas Rangers in 2006. The Angels paid for his career year, and the wheels fell off. He was eventually traded to the New York Mets after three seasons of zero WAR performance, with the Angels absorbing $21.5 million of the $23.5 million left on his contract.

         

    No. 3: 1B Albert PujolsDec. 8, 2011

    Terms: 10 years, $240 million (5.1x league avg)

    Pujols was at least productive in the early days of this contract, posting a 123 OPS+ and averaging 29 home runs, 98 RBI and 2.9 WAR over the first five seasons. Unfortunately, the 39-year-old is now a shell of his former MVP self, and his backloaded deal will pay $59 million over the next two seasons.

Los Angeles Dodgers

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    Jason Schmidt
    Jason SchmidtHarry How/Getty Images

    No. 1: SP Jason SchmidtDec. 6, 2006

    Terms: Three years, $47 million (5.4x league avg)

    Schmidt ended up making $4.7 million per start, as injuries limited him to just 10 starts and 43.1 innings during his three-year stint with the Dodgers. When he was able to take the mound, he served up a 6.02 ERA and 1.71 WHIP.

          

    No. 2: OF Andruw JonesDec. 6, 2007

    Terms: Two years, $36.2 million (6.1x league avg)

    With an $18.1 million average annual value, Jones was the fifth-highest-paid player in baseball when he joined the Dodgers. He hit a brutal .158/.256/.249 for a 35 OPS+ with three home runs in 238 plate appearances during 2008 after reporting to camp overweight and then undergoing knee surgery. He was released after one year.

         

    No. 3: OF Darryl Strawberry—Nov. 8, 1990

    Terms: Five years, $20.25 million (3.9x league avg)

    Strawberry finished ninth in NL MVP voting during his first season with the Dodgers, posting a 140 OPS+ with 28 home runs and 99 RBI. However, he played just 75 games the next two seasons before he was released to address his substance abuse problems. He was still owed $10.6 million when the team decided to cut ties.

Miami Marlins

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    Lynne Sladky/Associated Press

    No. 1: SP Wei-Yin ChenJan. 19, 2016

    Terms: Five years, $80 million (3.3x league avg)

    Not only did the Marlins vastly overpay to sign Chen, but they also surrendered a draft pick since he had rejected a qualifying offer from the Orioles. He has a 5.10 ERA over 358 innings so far during his time in Miami, and he was used exclusively as a reliever in 2019. There's nothing like an expensive and ineffective middle reliever.

          

    No. 2: RP Heath BellDec. 5, 2011

    Terms: Three years, $27 million (2.6x league avg)

    Bell was signed as part of an offseason spending spree that also included the additions of Mark Buehrle and Jose Reyes as the Marlins looked to usher in their new stadium with a contender. After three straight 40-save seasons with the San Diego Padres, Bell converted just 19 of 27 save chances with a 5.09 ERA in what would be his only season with Miami before he was dumped in a three-team trade.

         

    No. 3: SP Edinson Volquez—Nov. 28, 2016

    Terms: Two years, $22 million (2.5x league avg)

    The Marlins overlooked the 5.37 ERA and 1.55 WHIP Volquez posted with the Royals during the 2016 season and signed him to a two-year deal. He posted a 4.19 in 17 starts before undergoing Tommy John surgery in August 2017, which led to his release during the offseason.

Milwaukee Brewers

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    Jeffrey Hammonds
    Jeffrey HammondsTom Hauck/Getty Images

    No. 1: OF Jeffrey Hammonds—Dec. 22, 2000

    Terms: Three years, $21 million (3.1x league avg)

    Hammonds hit .335/.395/.529 with 20 home runs and 106 RBI during his lone season with the Rockies in 2000. Most of that damage came at Coors Field, where he batted .399/.465/.651 and hit 14 of his home runs, but the Brewers decided to ignore that fact. He provided Milwaukee with minus-0.3 WAR on its $21 million investment.

          

    No. 2: SP Jeff Suppan—Dec. 24, 2006

    Terms: Four years, $42 million (3.6x league avg)

    Never more than a middle-of-the-rotation starter, Suppan pitched like just that while averaging 192 innings with a 91 ERA+ over the first two years of his contract with the Brewers. His ERA then spiked to 5.29 in 2009, and he had a 7.84 ERA in 31 innings when he was released in June 2010.

         

    No. 3: SP Matt GarzaJan. 26, 2014

    Terms: Four years, $50 million (3.1x league avg)

    Garza was arguably the top free-agent starter in a class that included Ubaldo Jimenez, Ervin Santana, A.J. Burnett and Ricky Nolasco, and his $50 million contract represented a significant investment for the usually cautious Brewers. He was serviceable at best in posting a 4.65 ERA and 1.41 WHIP while averaging 23 starts and 132 innings over the life of the deal.

Minnesota Twins

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    Ricky Nolasco
    Ricky NolascoBrace Hemmelgarn/Getty Images

    No. 1: SP Ricky NolascoDec. 3, 2013

    Terms: Four years, $49 million (3x league avg)

    In another case of a team overpaying due to a thin crop of starting pitchers during the 2013-14 offseason, Nolasco had a less than stellar 4.37 ERA and 94 ERA+ when he hit the open market. He stuck around for two-and-a-half seasons, stumbling to a 5.44 ERA over 321 innings before he was flipped to the Angels.

          

    No. 2: SS Tsuyoshi NishiokaDec. 16, 2010

    Terms: Three years, $9 million (0.9x league avg)

    While the financial commitment was minimal, the Twins were banking on Nishioka being their starting shortstop in 2011. The 26-year-old was fresh off a batting title in Japan (.346/.423/.482), but that also represented a career year. He wound up playing just 71 games at the MLB level, hitting .215/.267/.236 for a 41 OPS+ in 254 plate appearances.

         

    No. 3: DH Rondell WhiteDec. 22, 2005

    Terms: Two years, $8.5 million (1.5x league avg)

    The idea behind this deal was that the oft-injured White might benefit from a full-time move to designated hitter in his age-34 season, thus unlocking some offensive upside. Instead, he hit .229/.266/.354 for a 62 OPS+ with 11 home runs in 474 plate appearances during his two-year stint with Minnesota before calling it a career.

New York Mets

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    Jason Bay
    Jason BayLisa Blumenfeld/Getty Images

    No. 1: OF Jason BayDec. 29, 2009

    Terms: Four years, $66 million (5.2x league avg)

    Over the first six full seasons of his career, Bay posted a 131 OPS+ while averaging 31 doubles, 30 home runs, 99 RBI and 3.6 WAR. No one could have seen his precipitous drop-off coming. Injuries immediately derailed his career, and the Mets wound up eating the final year of his contract after he produced just 1.8 WAR over the first three seasons.

         

    No. 2: OF Vince ColemanDec. 5, 1990

    Terms: Four years, $11.95 million (2.9x league avg)

    Coleman led the NL in steals during each of his first six seasons in the majors, averaging 92 thefts per year before he joined the Mets for the 1991 campaign. He played in only 235 games during the first three years of his contract, stealing just 99 total bases before he was traded to the Royals for Kevin McReynolds. All told, he was worth just 2.1 WAR for the Mets.

          

    No. 3: OF Bobby BonillaDec. 2, 1991

    Terms: Five years, $29 million (5.3x league avg)

    The infamous deferred money situation stems from Bonilla's return to the Mets in a trade with the Dodgers prior to the 1999 season, and therefore is not eligible for inclusion. However, his first go-around in New York does qualify. The fact that his $29 million contract made him the highest-paid player in baseball while the Mets received just 9.7 WAR out of the deal is enough to earn him a spot.

New York Yankees

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    Kei Igawa
    Kei IgawaKathy Willens/Associated Press

    No. 1: SP Kei IgawaDec. 27, 2006

    Terms: Five years, $46 million (3.1x league avg)

    Along with a five-year, $20 million base contract, the Yankees also paid a $26 million posting fee to sign Igawa. It quickly became apparent he didn't have the stuff to get MLB hitters out when he struggled to a 6.25 ERA in 67.2 innings as a rookie, and he spent the bulk of the next four seasons as a well-paid minor leaguer.

          

    No. 2: SP Carl PavanoDec. 20, 2004

    Terms: Four years, $39.9 million (3.7x league avg)

    Fresh off a career year with the Marlins in 2004, during which he finished sixth in NL Cy Young voting, Pavano cashed in at the perfect time. He would make just 26 starts during his four years with the Yankees, posting a 5.00 ERA and 1.46 WHIP in 145.2 total innings.

         

    No. 3: OF Jacoby EllsburyDec. 7, 2013

    Terms: Seven years, $153 million (5.2x league avg)

    There was no shortage of options for this No. 3 spot, with Hideki Irabu, Dave Collins, Ed Whitson and Jaret Wright, in particular, receiving strong consideration. Instead, we'll go with Ellsbury, who has not played in an MLB game since Sept. 30, 2017, and is still owed $21.1 million in 2020 and a $5 million buyout in 2021.

Oakland Athletics

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    Billy Butler
    Billy ButlerThearon W. Henderson/Getty Images

    No. 1: DH Billy ButlerNov. 19, 2014

    Terms: Three years, $30 million (2.4x league avg)

    Signing a 29-year-old designated hitter coming off a season in which he hit just nine home runs in 603 plate appearances was an odd way for the usually frugal Athletics to splurge in free agency. He was released midway through the second year of the contract after producing a 99 OPS+ and minus-0.6 WAR.

          

    No. 2: SP Esteban LoaizaNov. 29, 2005

    Terms: Three years, $21.4 million (2.5x league avg)

    Loaiza was an All-Star in 2003 and 2004, and he pitched to a 3.77 ERA with 173 strikeouts over 217 innings in 2005, so he had some appeal as a free-agent target. However, signing a 34-year-old to a lucrative three-year contract was a major risk for the Athletics, and it didn't pay off. After his disappointing first season, the Dodgers claimed him off waivers in Aug. 2007, saving Oakland a good chunk of change in the process.

         

    No. 3: RP Arthur Rhodes—Dec. 23, 2003

    Terms: Three years, $9 million (1.1x league avg)

    Signed to help solidify the Oakland bullpen after Keith Foulke walked in free agency, Rhodes converted just nine of 14 save chances with a 5.12 ERA and 1.73 WHIP in 37 appearances. He was traded to the Pittsburgh Pirates along with Mark Redman in exchange for catcher Jason Kendall during the 2004-05 offseason.

Philadelphia Phillies

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    Adam Eaton
    Adam EatonDrew Hallowell/Getty Images

    No. 1: SP Adam EatonNov. 27, 2006

    Terms: Three years, $24 million (2x league avg)

    What possessed the Phillies to give a lucrative three-year contract to a pitcher with a career 91 ERA+ who was coming off a season in which he logged a 5.12 ERA and 1.57 WHIP over 65 innings? The money only seemed to make things worse. Eaton was knocked around to the tune of a 6.10 ERA in two seasons before he was released.

          

    No. 2: 1B/OF Gregg JefferiesDec. 14, 1994

    Terms: Four years, $20 million (4x league avg)

    After hitting .335/.401/.487 in two seasons with the St. Louis Cardinals, Jefferies joined the Phillies and promptly forgot how to hit. The former phenom hit a lackluster .287/.340/.411 for a 97 OPS+ and 5.0 WAR. That wasn't bad, but it was nowhere near expectations.

         

    No. 3: 3B David BellDec. 2, 2002

    Terms: Four years, $17 million (1.7x league avg)

    During the four-year span from 1999 to 2002, Bell hit a respectable .260/.322/.416 while averaging 28 doubles, 17 home runs, 66 RBI and 2.2 WAR. However, he hit just .195 with a 57 OPS+ in his first season with the Phillies. And while he bounced back with a 4.4 WAR season in 2004—thanks in large part to his glove—he was worth just 1.4 WAR over the other three years of the contract.

Pittsburgh Pirates

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    Derek Bell
    Derek BellJonathan Daniel/Getty Images

    No. 1: OF Derek BellDec. 10, 2000

    Terms: Two years, $9.75 million (2.2x league avg)

    Two words: Operation Shutdown. Upon learning he would have to compete for the starting right field job following an injury-plagued 2001 season in which he hit .173 with five home runs over 46 games, Bell left the team on March 29 and was released two days later, ending his MLB career and an extremely underwhelming Pirates tenure.

          

    No. 2: SP Pete Schourek—Dec. 18, 1998

    Terms: Two years, $4 million (1.1x league avg)

    It's somewhat tricky to scrape up bad multiyear deals over the course of Pirates history, so we're stretching a bit here. Schourek had a 5.34 ERA in 113 innings during the first half of his modest two-year pact, and he was released the following March.

                

    No. 3: RP Daniel HudsonDec. 21, 2016

    Terms: Two years, $11 million (1.2x league avg)

    After a mediocre 4.38 ERA and 1.46 WHIP over 71 appearances in 2017, Hudson was traded to the Rays along with prospect Tristan Gray in exchange for outfielder Corey Dickerson. At least something good did come out of this otherwise disappointing signing.

San Diego Padres

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    Eric Hosmer
    Eric HosmerDylan Buell/Getty Images

    No. 1: 1B Eric HosmerFeb. 19, 2018

    Terms: Eight years, $144 million (4.8x league avg)

    Hosmer still has six seasons to prove he doesn't belong on this list. However, he also has $102 million left on his contract, and after a minus-0.3 WAR season in 2019, things are not trending in the right direction. This one could easily go from bad to worse.

          

    No. 2: OF Oscar GambleNov. 29, 1977

    Terms: Six years, $2.85 million (2.7x league avg)

    A career year with the White Sox in 1977 saw Gamble post a 162 OPS+ and slug a career-high 31 home runs, just in time for a trip to free agency. His home run total plummeted to just seven in his first and only season with the Padres, and he was traded to the Rangers along with $300,000 that offseason in a five-player deal.

         

    No. 3: SP James ShieldsFeb. 11, 2015

    Terms: Four years, $75 million (4.4x league avg)

    The Padres paid a 33-year-old Shields like an ace, and he pitched more like a middle-of-the-rotation arm with a 4.00 ERA (95 ERA+) in 269.2 innings before he was traded to the White Sox midway through his second season. That trade just so happened to net shortstop Fernando Tatis Jr. Otherwise, this one might have ranked higher.

San Francisco Giants

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    Barry Zito
    Barry ZitoJeff Chiu/Associated Press

    No. 1: SP Barry ZitoDec. 29, 2006

    Terms: Seven years, $126 million (5.9x league avg)

    To his credit, Zito stayed relatively healthy and chewed through 1,139.1 innings over the course of his seven-year deal. That said, his 4.62 ERA and 87 ERA+ are clearly not what the Giants signed up for when they agreed to what was then the largest contract ever for a pitcher, and he was consistently mediocre over the life of the contract.

          

    No. 2: OF Aaron RowandDec. 12, 2007

    Terms: Five years, $60 million (3.9x league avg)

    A strong contract year with the Phillies in 2007 that included his lone All-Star appearance netted Rowand a significant payday, but he never lived up to his salary in San Francisco. He had a sub-100 OPS+ in each of his four seasons with the team, posting just 2.6 WAR overall before he was released in Sept. 2011.

         

    No. 3: RP Mark Melancon—Dec. 5, 2016

    Terms: Four years, $62 million (4x league avg)

    Credit the current Giants front office for finding a way to unload the final year and a half of Melancon's contract while also bringing back a solid prospect in Tristan Beck. While he was once again a useful arm in 2019, he was signed to be a shutdown closer, and he ended up converting just 15 of 24 save chances during his time with the team.

Seattle Mariners

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    Chone Figgins
    Chone FigginsMarcus R. Donner/Associated Press

    No. 1: UT Chone FigginsDec. 8, 2009

    Terms: Four years, $36 million (2.8x league avg)

    Another beneficiary of a well-timed career year, Figgins had a 7.7 WAR season for the Angels in 2009 when he led the AL in walks (101) while tallying 42 steals and 114 runs scored with a .395 on-base percentage. He would hit only .227/.302/.283 for a 68 OPS+ and minus-0.9 WAR in three seasons in Seattle before he was released.

          

    No. 2: SP Carlos Silva—Dec. 20, 2007

    Terms: Four years, $48 million (4x league avg)

    What about a 4.42 ERA and 102 ERA+ in four seasons as a member of the Twins rotation made the Mariners think Silva was worth a four-year contract? He had a 6.81 ERA in 183.2 innings during the first two years of the deal before the Mariners flipped him to the Cubs for outfielder Milton Bradley.

         

    No. 3: 1B Scott SpiezioDec. 19, 2003

    Terms: Three years, $9.15 million (1.2x league avg)

    After a memorable four-year run with the Angels, Spiezio joined the Mariners for his age-31 season. After hitting a paltry .215/.288/.346 with 10 home runs in 415 plate appearances during his first year in Seattle, he played in only 29 games the following season and went 3-for-47 at the plate before he was released.

St. Louis Cardinals

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    Brett Cecil
    Brett CecilDilip Vishwanat/Getty Images

    No. 1: SP Danny JacksonDec. 12, 1994

    Terms: Three years, $10.8 million (3x league avg)

    After resurrecting his career in Philadelphia, Jackson signed a three-year deal with the Cardinals ahead of his age-33 season. Thyroid cancer kept him from living up to his potential and to that contract, and he finished his run in St. Louis with a 5.78 ERA and 1.61 WHIP in 155.2 innings despite being among the team's highest-paid players.

         

    No. 2: RP Brett CecilNov. 21, 2016

    Terms: Four years, $30.5 million (1.8x league avg)

    The relief pitcher market exploded after teams saw the success the Royals had in October with a stacked bullpen, and Cecil was one of the biggest beneficiaries. After pitching to a decent 3.88 ERA over 73 appearances in 2017, he surrendered a 6.89 ERA in 40 appearances the following year. He missed the entire 2019 season following surgery on his left wrist.

         

    No. 3: 1B Tino MartinezDec. 18, 2001

    Terms: Three years, $21 million (3x league avg)

    Expectations were high for Martinez, despite the fact that he was already 34 when he joined the Cardinals. He had a 105 OPS+ and averaged 18 home runs and 72 RBI in two seasons before he was traded to the Tampa Bay Rays in a salary dump. As Ryan Fagan of Sporting News noted, his propensity for speaking fondly of his time with the Yankees rubbed some fans the wrong way, making him the rare home player greeted by boos at Busch Stadium.

Tampa Bay Rays

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    Greg Vaughn
    Greg VaughnMitchell Layton/Getty Images

    No. 1: OF Greg VaughnDec. 13, 1999

    Terms: Four years, $34 million (3.9x league avg)

    The Rays tried to build a murderer's row when they signed Vaughn to join a lineup that also featured Jose Canseco, Fred McGriff and Vinny Castilla. While he hit 52 home runs during his first two seasons with the team, his .226 average and 5.3 WAR during his time in Tampa left a lot to be desired. The Rays released him prior to the final year of his contract.

          

    No. 2: OF Pat BurrellJan. 5, 2009

    Terms: Two years, $16 million (2.7x league avg)

    Looking to add a middle-of-the-order presence, the Rays signed Burrell after he hit 251 home runs over nine seasons with the Phillies. After a disappointing first season in Tampa, he was granted free agency in May 2010. He latched on with the Giants and helped lead them to a World Series title later that year.

         

    No. 3: SP Juan Guzman—Jan. 8, 2000

    Terms: Two years, $12.5 million (3.1x league avg)

    Far removed from his prime in Toronto, Guzman was running on fumes when he joined the Rays for his age-33 season. He made only one appearance, allowing seven hits, two walks and eight earned runs in 1.2 innings, before undergoing season-ending shoulder surgery that would end his career.

Texas Rangers

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    Chan Ho Park
    Chan Ho ParkJohn Williamson/Getty Images

    No. 1: SP Chan Ho ParkJan. 16, 2002

    Terms: Five years, $65 million (5.3x league avg)

    One of the best pitchers in the NL during his time wit the Dodgers, Park was coming off back-to-back 200-inning, 200-strikeout seasons when he joined the Rangers. The change of scenery proved detrimental, and when the dust settled, he had allowed a 5.79 ERA and 1.61 WHIP during his time with the Rangers.

          

    No. 2: OF Juan Gonzalez—Jan. 8, 2002

    Terms: Two years, $23 million (4.9x league avg)

    Already a two-time MVP, Gonzalez re-established himself as one of baseball's most feared sluggers in 2001 when he posted a 148 OPS+ with 35 home runs and 140 RBI. The Rangers paid handsomely to bring him back to where his career started, but he played in only 152 games over the course of the two-year deal, essentially producing one season's worth of quality stats for the price of two.

       

    No. 3: SP Mark Clark—Dec. 10, 1998

    Terms: Two years, $9 million (2.6x league avg)

    It's hard to pitch as poorly and as often as Clark did during his two seasons with the Rangers. The team trotted him out for 118.1 innings of work in his two seasons, and he logged an 8.37 ERA and 1.92 WHIP while allowing a staggering 169 hits and tallying nearly as many walks (58) as strikeouts (60).

Toronto Blue Jays

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    B.J. Ryan
    B.J. RyanKirby Lee/Getty Images

    No. 1: RP B.J. Ryan—Nov. 29, 2005

    Terms: Five years, $47 million (3.3x league avg)

    Ryan saved 36 games and made the AL All-Star team in his final season with the Orioles, and it was more of the same in his Blue Jays debut with 38 saves and a pristine 1.37 ERA. He had another strong season in 2008 with an injury-plagued campaign sandwiched in between, but that was the end of his productivity. A $47 million payout for only two solid seasons is enough to take the No. 1 spot here.

          

    No. 2: SP Erik HansonDec. 22, 1995

    Terms: Three years, $9.4 million (2.4x league avg)

    An All-Star in 1995 when he went 15-5 with a 4.24 ERA (115 ERA+) as a member of the Red Sox, Hanson worked 214.2 innings in his first season with the Blue Jays, albeit with a 5.41 ERA and 1.61 WHIP. He made only 14 more appearances over the final two seasons of the deal, finishing his time in Toronto with a 5.68 ERA in 278.2 innings.

         

    No. 3: 3B Corey KoskieDec. 14, 2004

    Terms: Three years, $17.5 million (2.2x league avg)

    After establishing himself as one of the more productive third basemen in baseball during his seven seasons with the Twins, Koskie joined the Blue Jays on a three-year deal. The Canada native hit only .249 with a 94 OPS+ in 2005 and was shipped to Milwaukee the following offseason after Toronto acquired Troy Glaus from the Diamondbacks.

Washington Nationals

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    Jayson Werth
    Jayson WerthMitchell Layton/Getty Images

    No. 1: OF Jayson WerthDec. 5, 2010

    Terms: Seven years, $126 million (4.8x league avg)

    While Werth was sporadically productive over the course of his seven-year megadeal, he contributed only 8.8 WAR during his time with the Nationals, which hardly lived up to the contract. The two-year span from 2013 to 2014 when he stayed healthy enough to average 138 games was a glimpse of what could have been, as he hit .304 with a 143 OPS+ and racked up 8.7 WAR.

          

    No. 2: C Matt WietersFeb. 24, 2017

    Terms: Two years, $21 million (2.4x league avg)

    A year after accepting a qualifying offer, Wieters settled for a slight pay cut when he joined the Nationals. After he posted a brutal 62 OPS+ in the first year of the deal, injuries limited him to only 76 games in 2018, forcing the Nats to rely on the likes of Spencer Kieboom and Pedro Severino for much of the year.

         

    No. 3: SS Cristian GuzmanNov. 16, 2004

    Terms: Four years, $16.8 million (1.5x league avg)

    After posting minus-1.4 WAR in 2005, missing the entire 2006 season to recover from shoulder surgery and playing in only 46 games in 2007, Guzman turned in 4.6 WAR in the final year of this contract. That helped him coax another two-year, $16 million deal out of the Nats, which ended up being a mistake as well.

        

    All stats courtesy of Baseball Reference and FanGraphs, while contract information came from a wide variety of sources, including Baseball Prospectus, Spotrac and old news articles. Average salary data via ESPN.com and Statista.com and can be found compiled in this doc.