The Worst Free-Agent Signing in MLB History at Each Position

Joel Reuter@JoelReuterBRFeatured ColumnistDecember 22, 2021

The Worst Free-Agent Signing in MLB History at Each Position

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    Stephan Savoia/Associated Press

    "The best-laid plans of mice and men often go awry."

    That idiom is the perfect embodiment of the risk and reward that goes into shelling out millions of dollars on the MLB free-agent market.

    Yesterday, we took a look at the best free-agent signing in MLB history at each position, highlighting guys like Greg Maddux (ATL), Randy Johnson (ARI) and Manny Ramirez (BOS) who helped lead their teams to World Series titles while putting up superstar-level production.

    Now it's time for the opposite end of things.

    Ahead we've selected the worst of the worst at each position, focusing on production relative to expectations, and more importantly relative to salary. The longer the deal and the bigger the financial commitment, the more likely a deal that went south was to earn a spot on this list.

    Only outside free-agency signings were considered—no players re-signing with their previous team, no contract extensions, no trade or waiver additions.

    We've also included a handful of dishonorable mentions at each position, but feel free to suggest anyone else you feel is worthy of consideration.

    Off we go!

Catcher: Todd Hundley, Chicago Cubs

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    Tom Hauck/Getty Images

    Date: Dec. 19, 2000

    Terms: Four years, $23.5 million

    It was a big story on the North Side when Todd Hundleya Chicago-area native and the son of longtime Cubs catcher Randy Hundley—came home and brought his power bat with him by inking a four-year deal prior to the 2001 season.

    Hundley enjoyed a breakout season in 1996 when he slugged 41 home runs as a member of the New York Mets, and he followed that up with another 30-homer season and a second straight All-Star appearance the following year.

    He reached free agency coming off another strong year in 2000, as he logged a 143 OPS+ with 24 home runs and 70 RBI with the Los Angeles Dodgers. Unfortunately, the Cubs saw nothing close to that level of production during his time with the team.

    He hit .199/.285/.398 for a 79 OPS+ with 28 home runs in 171 games over the first two years of the contract. After that, he was shipped back to the Dodgers in a trade that brought Eric Karros and Mark Grudzielanek the other way.

    Also Considered: None

First Baseman: Mo Vaughn, Anaheim Angels

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    Damian Dovarganes/Associated Press

    Date: Dec. 11, 1998

    Terms: Six years, $80 million

    One of the most feared sluggers in baseball during the 1990s, Mo Vaughn hit .315/.405/.569 for a 148 OPS+ while averaging 36 home runs and 110 RBI during his six seasons as an everyday player for the Boston Red Sox.

    That impressive run with the team concluded following the 1998 season when he reached free agency for the first time in his career. His foray into the open market came at the perfect time, as he hit .337/.402/.591 with 40 home runs and 115 RBI to finish fourth in AL MVP balloting during the '98 season.

    In search of a big bat to join the homegrown trio of Jim Edmonds, Tim Salmon and Garret Anderson in the middle of the batting order, the Anaheim Angels gave him a massive six-year, $80 million deal.

    After productive seasons in 1999 (119 OPS+, 33 HR, 108 RBI) and 2000 (115 OPS+, 36 HR, 117 RBI), he missed the entire 2001 season with a ruptured tendon in his left arm, and he was traded to the New York Mets for Kevin Appier prior to the 2002 season.

    He battled knee injuries from there, playing in just 166 more games and posting minus-1.2 WAR in his three seasons with the Mets.

    Also Considered: Eric Hosmer (SD), Adam LaRoche (CWS), Tino Martinez (STL), Albert Pujols (LAA)

Second Baseman: Chone Figgins, Seattle Mariners

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    Marcus R. Donner/Associated Press

    Date: Dec. 8, 2009

    Terms: Four years, $36 million

    A valuable Swiss Army knife during his time with the Los Angeles Angels, Chone Figgins hit the free-agent market at the perfect time.

    The 32-year-old had put together a career year in 2009 when he hit .298 with a .395 on-base percentage and an AL-leading 101 walks, adding 42 steals and 114 runs scored as a dynamic table-setter with a career-high 7.7 WAR.

    That netted him a four-year deal from the Seattle Mariners, and he was slotted in as the team's everyday second baseman for the 2010 season.

    In his Mariners debut, he hit .259/.340/.306 for an 84 OPS+ with 42 steals and 1.2 WAR, and that proved to be the high point of his tenure with the team.

    He played in 147 games over the next two seasons, logging an ugly minus-2.1 WAR along the way, before he was designated for assignment with $8 million left on his contract.

    Also Considered: Omar Infante (KC)

Third Baseman: Pablo Sandoval, Boston Red Sox

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    Stephan Savoia/Associated Press

    Date: Nov. 25, 2014

    Terms: Five years, $95 million

    Pablo Sandoval helped lead the San Francisco Giants to a third World Series title in five years during the 2014 season, contributing 3.2 WAR during the regular season before batting .366/.423/.465 with 26 hits in 17 games during the postseason.

    The Boston Red Sox moved quickly in free agency that offseason, signing him to a five-year, $95 million deal on the same day that they agreed to a four-year, $88 million contract with Hanley Ramirez.

    The "Kung Fu Panda" hit .242/.292/.366 with 10 home runs and 47 RBI in 126 games during his first year in Boston and then played just three games the following year before undergoing surgery to repair a torn labrum in his left shoulder.

    A knee sprain and a viral infection limited him once again in 2017, and he was hitting .212/.269/.354 in 108 plate appearances when he was designated for assignment on July 14.

    All told, he produced minus-1.6 WAR in a Red Sox uniform, and to make matters worse, he found his way back to San Francisco and returned to productive form as a part-time player and pinch hitter.

    Also Considered: David Bell (PHI), Corey Koskie (TOR), Dean Palmer (DET)

Shortstop: Jose Reyes, Miami Marlins

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    LM Otero/Associated Press

    Date: Dec. 7, 2011

    Terms: Six years, $106 million

    With a fancy new ballpark ready to open, the Miami Marlins set out to make a splash during the 2011-12 MLB offseason.

    They walked away with shortstop Jose Reyes (6/$106M), starter Mark Buehrle (4/$58M) and closer Heath Bell (3/$27M) as their free-agency haul, and a year later all three guys were gone.

    After a 93-loss season in 2012, the Marlins packaged Reyes and Buehrle with Josh Johnson, John Buck and Emilio Bonifacio and sent them to the Toronto Blue Jays in exchange for seven players.

    Reyes hit .287 with 60 extra-base hits and 40 steals in his lone season with the Marlins, and he was productive during his first two seasons in Toronto as well, but the back end of the contract was a disaster.

    He was eventually traded to the Colorado Rockies in the Troy Tulowitzki deal and then suspended 59 games for violating the league's domestic violence policy. The Rockies designated him for assignment on June 15, 2016, when he returned from his suspension, cutting ties with more than $39 million remaining on his contract.

    All told, his $106 million contract amounted to 9.3 WAR worth of production.

    Also Considered: Cristian Guzman (WAS), Julio Lugo (BOS)

Outfielder: Josh Hamilton, Los Angeles Angels

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    Victor Decolongon/Getty Images

    Date: Dec. 15, 2012

    Terms: Five years, $125 million

    A year after signing Albert Pujols to a massive 10-year deal, the Los Angeles Angels made a splash once again by inking slugger Josh Hamilton to a five-year deal with a $25 million annual value.

    After posting a 141 OPS+ with 43 home runs and 128 RBI in his final season with the Texas Rangers, two years after he won AL MVP honors, expectations were high for his middle-of-the-order production. Instead, he hit a middling .250/.307/.432 for a 108 OPS+ with 21 home runs and 79 RBI in 151 games in his first year with the team.

    Things only got worse from there.

    He was limited to 89 games in 2014 with a thumb injury, and he underwent shoulder surgery prior to the 2015 season. During his recovery, he suffered a relapse into his drug addiction, and the Angels ultimately facilitated a trade that sent him back to the Rangers for a player to be named on April 27, 2015.

    They ate roughly $62.5 million of his remaining salary in the deal, and he finished his Angels tenure with 2.7 WAR in 240 games played.

Outfielder: B.J. Upton, Atlanta Braves

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    John Bazemore/Associated Press

    Date: Nov. 29, 2012

    Terms: Five years, $75.25 million

    It's generally a result of injuries or a decline in production that keeps a player from living up to a big free-agency contract, but sometimes, a deal just looks bad from the start.

    This one falls firmly into that second category.

    B.J. Upton looked like a budding superstar when he hit .300/.386/.508 with 24 home runs, 82 RBI and 22 steals as a 22-year-old in 2007, and while he failed to match that level of production in the years that followed, his mix of power and speed continued to mask some of the shortcomings in his game.

    When he reached free agency after the 2012 season, he was coming off a 28-homer, 31-steal season, but behind those impressive counting numbers he had an ugly .298 on-base percentage and a 26.7 percent strikeout rate.

    Undeterred by those red flags, the Atlanta Braves signed him to a five-year, $75.25 million deal, and his production promptly bottomed out.

    He hit .198/.279/.314 for a 66 OPS+ with a 31.5 percent strikeout rate and minus-1.7 WAR in two seasons before he was packaged along with All-Star closer Craig Kimbrel and traded to the San Diego Padres where he didn't fare much better.

Outfielder: Albert Belle, Baltimore Orioles

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    HEATHER HALL/Getty Images

    Date: Dec. 1, 1998

    Terms: Five years, $65 million

    After a stellar eight-year run in Cleveland, slugger Albert Belle joined the Chicago White Sox on a five-year, $55 million deal prior to the 1997 season that made him the highest-paid player in baseball.

    That contract contained a unique clause that demanded he remain one of the three highest-paid players in the sport or be allowed to opt out of the contract and re-enter free agency. He exercised the clause after the 1998 season, and when the White Sox balked at offering him the necessary raise, he hit the open market.

    The Baltimore Orioles swooped in with a five-year, $65 million deal, tying him with Mike Piazza for the third-highest average salary in baseball, behind only Mo Vaughn ($13.3M) and Randy Johnson ($13.1M). He hit .297/.400/.541 for a 143 OPS+ with 37 home runs and 117 RBI in his first season with the Orioles.

    However, he played just one more season after that before a degenerative hip condition ended his career. He remained on the 40-man roster for the final three years of the deal as a condition of his contract, and that allowed the Orioles to recoup much of his salary through insurance.

    Still, it's far from what was expected when he was given the big contract. 

    Also Considered: Jason Bay (NYM), Derek Bell (PIT), Bobby Bonilla (NYM), Michael Bourn (CLE), Milton Bradley (CHC), Rusney Castillo (BOS), Carl Crawford (BOS), Ian Desmond (COL), Jacoby Ellsbury (NYY), Dexter Fowler (STL), Jeffrey Hammonds (MIL), Andruw Jones (LAD), Gary Matthews Jr. (LAA), Nick Swisher (CLE), Yasmany Tomas (ARI)

Right-Handed Starting Pitcher: Carl Pavano, New York Yankees

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    FRANK FRANKLIN II/Associated Press

    Date: Dec. 20, 2004

    Terms: Four years, $39.95 million

    After helping the Florida Marlins win a World Series in 2003, Carl Pavano had the best season of his career the following year, going 18-8 with a 3.00 ERA, 1.17 WHIP and 139 strikeouts in 222.1 innings.

    His career lined up perfectly with free agency, and he parlayed it into a four-year deal from a New York Yankees team hard at work rebuilding its starting rotation. They also acquired Randy Johnson in a trade with the Arizona Diamondbacks and signed Jaret Wright to a three-year, $21 million deal.

    Pavano's first season in pinstripes saw him make just 17 starts before he was slowed by a right shoulder injury, and things only got worse from there. He then missed time the next spring with a strained buttocks before dealing with shoulder inflammation and then breaking two ribs in a car accident.

    The following spring, he was called out by veteran Mike Mussina, who said he needed to prove he wanted to pitch for the Yankees. He responded by making a grand total of nine more starts with the team over the final two years of his contract.

    His final stat line in four years with the Yankees: 26 GS, 5.00 ERA, 1.45 WHIP, 145.2 IP, 0.4 WAR

    Also Considered: Wayne Garland (CLE), Edwin Jackson (CHC), Ubaldo Jimenez (BAL), Jaime Navarro (CWS), Ricky Nolasco (MIN), Russ Ortiz (ARI), Chan Ho Park (TEX), Jason Schmidt (LAD), Carlos Silva (SEA), Jordan Zimmermann (DET)

Left-Handed Starting Pitcher: Mike Hampton, Colorado Rockies

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    Brian Bahr/Getty Images

    Date: Dec. 12, 2000

    Terms: Eight years, $121 million

    The Colorado Rockies were intent on building a competitive starting rotation during the 2000-01 offseason, and they spent big to try to do it, adding left-handers Mike Hampton (8/$121M) and Denny Neagle (5/$51M) in free agency.

    Hampton went 22-4 with a 2.90 ERA in 239 innings to finish runner-up in NL Cy Young voting in 1999, and he followed that up with a 3.14 ERA in 217.2 innings before hitting the open market at the age of 27, so the expectation was that he would be the ace of the staff.

    Coors Field had other ideas.

    He had a 5.41 ERA (99 ERA+) in 203 innings in the first year of his contract and an even uglier 6.15 ERA (78 ERA+) the following year. After that, he was traded along with Juan Pierre to the Florida Marlins in exchange for Preston Wilson, Charles Johnson and two others.

    The Marlins flipped him again two days later to the Atlanta Braves, and he pitched well in 2003 and 2004 before injuries started to pile up.

    Also Considered: Wei-Yin Chen (MIA), Kei Igawa (NYY), Scott Kazmir (LAD), Eric Milton (CIN), Denny Neagle (COL), Greg Swindell (HOU)

Relief Pitcher: Mark Davis, Kansas City Royals

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    Mitchell Layton/Getty Images

    Date: Dec. 11, 1989

    Terms: Four years, $13 million

    Fresh off 1989 NL Cy Young honors with the San Diego Padres, lefty reliever Mark Davis became baseball's highest-paid player in terms of annual value when he signed this four-year contract with the Kansas City Royals.

    A year after converting 44 of 48 save chances with a 1.85 ERA, 1.05 WHIP and 92 strikeouts in 92.2 innings to edge out Houston Astros ace Mike Scott for top pitcher honors in the National League, he stumbled to a 5.11 ERA with four blown saves in 10 chances over 53 appearances in his first season in the American League.

    Things didn't improve from there and he lasted two-and-a-half seasons in Kansas City, posting a 5.31 ERA with seven saves in 95 appearances before he was traded to the Atlanta Braves at the 1992 trade deadline for reliever Juan Berenguer.

    Also Considered: Heath Bell (MIA), B.J. Ryan (TOR), Bruce Sutter (ATL)


    All stats courtesy of Baseball Reference and FanGraphs.


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