Every MLB Team's Biggest Free Agency Flop Since 2000

Buyer beware.

That's a sign that should be hanging in every MLB front office while they mull over potentially offering millions of dollars to players in free agency.

Spending money on free agents is a necessary evil in building a World Series contender, and there are inevitably going to be players who fail to live up to expectations whether it's a result of injuries, regression or them simply being overpaid from the start.

Ahead we've highlighted each team's biggest free agency flop since the 2000 season, based on production relative to expectations and the overall cost of the contract that each player signed.

Buckle up for a cringe-worthy walk down memory lane.

Date: Dec, 17, 2019
Contract: Five years, $85 million

Madison Bumgarner was the highest-paid player on the D-backs roster during their unexpected run to the World Series in 2023. However, he didn't play for the team after April 26 when he was released with a 10.26 ERA after four starts.

A workhorse ace during his 11 seasons with the San Francisco Giants, Bumgarner simply didn't have much left in the tank by the time he reached free agency. He finished with a 5.23 ERA in 363.1 innings during his time in the desert, and the D-backs are still on the hook for another $14 million in 2024.

Runner-Up: SP Russ Ortiz (Dec. 11, 2004)

Date: Nov. 29, 2012
Contract: Five years, $75.25 million

Outfielder B.J. Upton had a 28-homer, 31-steal contract year for the Tampa Bay Rays in 2012, but it was accompanied by a lackluster .246/.298/.454 batting line and 169 strikeouts in 146 games.

Those red flags didn't stop the Braves from paying top dollar over a five-year deal, and he went on to hit .198 with a 66 OPS+ and minus-1.8 WAR in two seasons in Atlanta before he was dumped on the San Diego Padres in a package deal with All-Star closer Craig Kimbrel.

Runner-Up: SP Kenshin Kawakami (Jan. 13, 2009)

Date: Jan. 21, 2016
Contract: Seven years, $161 million

Slugger Chris Davis tested free agency before finding his way back to the Baltimore Orioles on a massive seven-year, $161 million deal, so this one counts as a free-agent signing rather than an extension.

He had a 110 OPS+ and 38 home runs in the first season of his new contract, but things quickly devolved from there and he had an all-time awful season in 2018 (-3.3 WAR, 36.8 K%). He eventually called it quits late in the 2021 season, but the Orioles will still be paying him in 2025 after the final year of his contract was restructured and deferred.

The final result of his seven-year deal: 534 games, 92 home runs, 762 strikeouts and minus-2.7 WAR.

Runner-Up: SP Ubaldo Jiménez (Feb. 19, 2014)

Date: Nov. 25, 2014
Contract: Five years, $95 million

The Red Sox spent big to retool their offense during the 2014-15 offseason, moving quickly to sign Sandoval and Hanley Ramirez to a four-year, $88 million deal on the same day in late November.

Sandoval went on to hit .237 with a 71 OPS+ and minus-1.6 WAR in 161 games over three seasons with the Red Sox before he was released on July 19, 2017. He then found his way back to the San Francisco Giants where he re-emerged as a productive bench player while Boston paid the bulk of his salary.

Runner-Up: OF Rusney Castillo (Aug. 23, 2014)

Date: Jan. 9, 2009
Contract: Three years, $30 million

Jason Heyward and Alfonso Soriano will be popular picks here as they simply did not live up to the lucrative deals they signed, but both players were positive contributors at some point during their long-term deals and by all accounts good teammates.

The same can't be said about Milton Bradley, who clashed with teammates and manager Lou Piniella before he was ultimately dismissed from the team in late September 2009. After one year in Chicago, the Cubs flipped him to the Seattle Mariners in exchange for Carlos Silvia in a swap of bad contracts.

Runner-Up: OF Jason Heyward (Dec. 15, 2015)

Date: Dec. 3, 2010
Contract: Four years, $56 million

Slugger Adam Dunn landed on the South Side with a thud in 2011, hitting .159 with almost three times as many strikeouts (177) as hits (66) in a minus-2.9 WAR season.

He rebounded with a 115 OPS+ and 41 home runs to earn an All-Star selection the following year, but the final two seasons of his contract were mediocre at best. He wrapped up his $56 million deal with minus-0.4 WAR in 528 games with the White Sox.

Runner-Up: C Yasmani Grandal (Nov. 21, 2019)

Date: Dec. 5, 2019
Contract: Four years, $64 million

The Reds rarely dive into the deep end of the free agency pool, but they made an exception to sign Mike Moustakas who had just logged a 114 OPS+ and 35 home runs with the Milwaukee Brewers while earning his third career All-Star selection.

He had a 105 OPS+ with 17 extra-base hits in 163 plate appearances during the shortened 2020 season, but that proved to be his high point in Cincinnati. After struggling to a .212 average and 72 OPS+ in 140 games over the next two seasons while battling injuries, the Reds released him with $22 million left on his contract last winter.

Runner-Up: SP Eric Milton (Dec. 28, 2004)

Date: Jan. 3, 2013
Contract: Four years, $56 million

In a rare free agency splurge, Cleveland signed outfielders Nick Swisher (4/$56M) and Michael Bourn (4/$48M) during the 2012-13 offseason, and both players failed to live up to those pay days.

Swisher had a 115 OPS+ with 22 home runs and 63 RBI in a 3.7-WAR season in 2013, but his production plummeted from there. He was eventually traded to the Atlanta Braves along with Bourn and cash midway through the 2015 season in a salary dump that brought back third baseman Chris Johnson's bad contract.

Runner-Up: OF Michael Bourn (Feb. 15, 2013)

Date: Dec. 13, 2016
Contract: Five years, $70 million

It might be only a matter of time before Kris Bryant is the runaway choice for the Colorado Rockies, but two seasons into his seven-year, $182 million deal there is still time for him to change the narrative.

The Mike Hampton contract is also a strong contender, but the Rockies managed to get out from under that deal when he was traded to the Atlanta Braves after two seasons in a complicated three-team swap that also included the Marlins.

Instead, the nod goes to Ian Desmond, even though his five-year, $70 million contract ended up being a three-year, $45 million deal when he opted out of the 2020 and 2021 seasons due to the COVID-19 pandemic. He finished his Rockies career with minus-2.5 WAR in 395 games.

Runner-Up: SP Mike Hampton (Dec. 12, 2000)

Date: Nov. 30, 2015
Contract: Five years, $110 million

A quick side-by-side comparison of Jordan Zimmermann's final five seasons with the Washington Nationals and his five seasons with the Detroit Tigers tells the story:

• 2011-15: 155 GS, 66-43, 3.14 ERA, 1.14 WHIP, 4.6 BB%, 19.8 K%, 18.9 WAR
• 2016-20: 97 GS, 25-41, 5.63 ERA, 1.44 WHIP, 5.5 BB%, 16.3 K%, 2.0 WAR

His almost immediate drop-off in Detroit after establishing himself as a reliable frontend starter for the Nationals is one of the more puzzling declines in recent memory.

Runner-Up: DH Victor Martinez (Nov. 14, 2014)

Date: Nov. 24, 2006
Contract: Two years, $12.5 million

Generally speaking, the Astros have done a good job avoiding bad contracts over the past decade plus while building a perennial title contender through homegrown talent and shrewd moves on the trade market, but there were some duds during the 2000s.

Veteran Woody Williams was entering his age-40 season when the Astros signed him to a two-year deal, and while he had finished with a 3.65 ERA in 145.1 innings the previous year with the San Diego Padres, his 4.90 FIP told a different story. He scuffled to a 5.27 ERA and 1.43 WHIP in 188 innings in his first year with the Astros, and he was released before Opening Day in 2008.

Runner-Up: 2B Kaz Matsui (Nov. 30, 2007)

Date: Dec. 16, 2013
Contract: Four years, $30.25 million

A useful super-utility player during his time with the Detroit Tigers and Atlanta Braves who was even an All-Star in 2010, Omar Infante was one of the least productive hitters in baseball during his time with the Kansas City Royals.

He hit .238/.269/.328 for a 63 OPS+ in 1,179 plate appearances with the team and tallied minus-0.3 WAR in 298 games before he was released on June 21 during his third season with the team. Fans won't soon forget when he was almost voted to start the All-Star Game in 2015 when Royals fans stuffed the ballot boxes.

Runner-Up: OF Jose Guillen (Dec. 4, 2007)

Date: Dec. 15, 2012
Contract: Five years, $125 million

How long before Anthony Rendon claims the No. 1 spot for the Los Angeles Angels?

The oft-injured third baseman is four years and roughly $129 million into his seven-year, $245 million contract, and so far he has yet to play more than 58 games in a season while tallying 3.1 WAR in 200 total games in an Angels uniform.

That's still more than the Angels got out of their $125 million investment in Josh Hamilton. The 2010 AL MVP managed just 2.8 WAR in two seasons before the Angels ate $68.4 million of the $75 million remaining on his contract to send him back to the Texas Rangers.

Runner-Up: 3B Anthony Rendon (Dec. 13, 2019)

Date: Dec. 6, 2006
Contract: Three years, $47 million

A perennial NL Cy Young contender during his six seasons with the San Francisco Giants, right-hander Jason Schmidt joined the rival Los Angeles Dodgers when he reached free agency prior to the 2007 season.

The Dodgers ended up paying him $4.7 million per start when injuries limited him to 10 appearances and 43.1 innings during the life of his three-year contract, and he struggled to a 6.02 ERA in the rare instances he was able to take the mound.

Runner-Up: SP Trevor Bauer (Feb. 11, 2021)

Date: Jan. 19, 2016
Contract: Five years, $80 million

Even in today's market where middling veteran starters like Kyle Gibson are worth $13 million, the long-term deal that Wei-Yin Chen signed with the Miami Marlins prior to the 2016 season would look like a massive overpay.

He posted a 4.75 ERA and 1.28 WHIP in 289.2 innings over the first three years of his contract before he was demoted to the bullpen in 2019, pitching to a 6.59 ERA in 45 appearances of mostly mop-up duty. The Marlins ate $22 million and released him ahead of the final year of his deal in 2020.

Runner-Up: RP Heath Bell (Dec. 5, 2011)

Date: Dec. 24, 2006
Contract: Four years, $42 million

Even at his best, Jeff Suppan was never more than a middle-of-the-rotation starter, albeit one who consistently tallied 30 starts and 190 innings throughout the early part of his career.

He made 95 starts during his first three seasons in Milwaukee, but consistently pitched below replacement-level with a 4.93 ERA and 87 ERA+ in 546 innings. He was released in June of the final season of his contract with a 7.84 ERA in 31 innings pitching mostly out of the bullpen.

Runner-Up: OF Jeffrey Hammonds (Dec. 22, 2000)

Date: Dec. 3, 2013
Contract: Four years, $49 million

Ricky Nolasco had one of the best seasons of his career in 2013, going 13-11 with a 3.70 ERA, 1.21 WHIP and 165 strikeouts in 199.1 innings over 33 starts while joining a contending Los Angeles Dodgers team at the trade deadline.

He had a 5.44 ERA and 1.47 WHIP in 321 innings with the Twins before they cut their losses and flipped him to the Los Angeles Angels along with top prospect Alex Meyer midway through his third season in a four-player deal that brought back Héctor Santiago and Alan Busenitz.

Runner-Up: SS Tsuyoshi Nishioka (Dec. 16, 2010)

Date: Dec. 29, 2009
Contract: Four years, $66 million

Outfielder Jason Bay was a star for the Pittsburgh Pirates before he was traded to the Boston Red Sox in the Manny Ramirez blockbuster deal. In a contract year with the Red Sox in 2009, he posted a 134 OPS+ with 29 doubles, 36 home runs, 119 RBI and 5.2 WAR.

Still only 31 years old when he joined the New York Mets, he hit just .234/.318/.369 for a 90 OPS+ with 1.8 WAR over three injury-plagued seasons before the Mets released him with $18.1 million remaining on his deal.

Runner-Up: SP Oliver Pérez (Feb. 2, 2009)

Date: Dec. 7, 2013
Contract: Seven years, $153 million

Starting pitcher flops like Kei Igawa, Carl Pavano, Jaret Wright and A.J. Burnett are all worthy of a mention here, but all of those signings pale in comparison to the fantastic failure that was the Jacoby Ellsbury deal.

He tallied 9.8 WAR while averaging 130 games per season over the first four years of the contract, but he didn't play a single game while earning $68.4 million over his final three seasons on the books and his time in New York came to a contentious end.

Runner-Up: SP Kei Igawa (Dec. 27, 2006)

Date: Nov. 19, 2014
Contract: Three years, $30 million

Designated hitter Billy Butler was a head-scratching splurge by the usually tight-fisted Oakland Athletics from the start.

He hit .251/.323/.390 for a 98 OPS+ with 15 home runs, 65 RBI and minus-0.6 WAR in 151 games during his first season with the team. From there he played in only 85 games the following year before he was released in September, and the final year of his contract became a sunk cost.

Runner-Up: SP Esteban Loaiza (Nov. 29, 2005)

Date: March 12, 2018
Contract: Three years, $75 million

After emerging as one of baseball's elite starting pitchers while helping to lead the Chicago Cubs to a World Series title, Jake Arrieta hit the open market ahead of his age-32 season and signed a deal that made him one of the highest-paid players in baseball.

He posted a 3.96 ERA and 138 strikeouts in 172.2 innings in his Phillies debut, and things only went downhill from there. He finished his time in Philadelphia with a 4.36 ERA and 1.39 WHIP in 352.2 total innings, and he was also not shy about criticizing his teammates and the organization along the way.

Runner-Up: SP Adam Eaton (Nov. 27, 2006)

Date: Dec. 10, 2000
Contract: Two years, $9.75 million

A productive corner outfielder coming off an 18-homer, 69-RBI season with the New York Mets in 2000, the Pittsburgh Pirates signed Derek Bell to help bolster an offense that included Brian Giles, Aramis Ramirez, Jason Kendall and Kevin Young.

He hit just .173 over 46 games in an injury-plagued first season in Pittsburgh, then went into his infamous "Operation Shutdown" the following spring when he was informed he would have to compete for the starting right field job. He left the team on March 29, was released two days later, and never played another MLB game.

Runner-Up: OF Jeromy Burnitz (Jan. 9, 2006)

Date: Feb. 19, 2018
Contract: Eight years, $144 million

Eric Hosmer had the best season of his career in a contract year with the Kansas City Royals in 2017, hitting .318/.385/.498 for a 133 OPS+ with 31 doubles, 25 home runs, 94 RBI and 4.3 WAR.

Only 28 years old when he hit free agency for the first time, the Padres signed him to a massive eight-year deal to serve as a cornerstone piece of their rebuilding efforts. He logged a 103 OPS+ and 3.7 WAR in five seasons before he was traded to the Boston Red Sox at the 2022 deadline in a salary dump.

The Padres still owe him another $26 million over the next two years, minus the league minimum that the Red Sox are on the hook for after releasing him.

Runner-Up: SP James Shields (Feb. 11, 2015)

Date: Dec. 29, 2006
Contract: Seven years, $126 million

Yes, Barry Zito stayed healthy enough to chew through 1,139.1 innings during his seven seasons with the San Francisco Giants. And yes, his gem (7.2 IP, 6 H, 0 ER) against the St. Louis Cardinals in Game 5 of the 2012 NLCS stands as a memorable moment from the team's World Series run that year.

That said, a 4.62 ERA and 87 ERA+ with zero All-Star selections and zero Cy Young votes in seven seasons is not what the Giants had in mind when they signed the southpaw to what was at the time the largest contract ever given to a pitcher.

Runner-Up: OF Aaron Rowand (Dec. 12, 2007)

Date: Dec. 8, 2009
Contract: Four years, $36 million

Speedy Chone Figgins is a prime example of how a well-timed career year can earn a good-not-great player a ton of money. He hit .298 with a .395 on-base percentage and 110 OPS+ during the 2009 season, tallying 183 hits, 101 walks, 42 steals and 114 runs scored in a 7.7-WAR season.

He had a decent first season in Seattle, albeit with a dip in production across the board, but hit just .185/.249/.253 with minus-2.1 WAR in 147 games over the next two years. The Mariners released him ahead of the final season of his contract.

Runner-Up: SP Carlos Silva (Dec. 20, 2007)

Date: Dec. 9, 2016
Contract: Five years, $82.5 million

On the heels of serving as a table-setting leadoff hitter for the Chicago Cubs en route to a long-awaited World Series title in 2016, center fielder Dexter Fowler jumped ship and joined the rival St. Louis Cardinals in free agency.

Injuries limited him to 208 games over his first two seasons with the Cardinals, and he ended up tallying just 1.8 WAR in four seasons with the team before he was traded to the Los Angeles Angels for a player to be named ahead of the final year of his contract.

Runner-Up: RP Brett Cecil (Nov. 21, 2016)

Date: Jan. 5, 2009
Contract: Two years, $16 million

It's not often the Tampa Bay Rays open up their wallets, so the choices here were few and far between, but the Pat Burrell signing can only be classified as a flop.

Fresh off a surprise trip to the World Series, the Rays added Burrell hoping he could provide some power in the middle of the lineup. Instead, he hit .221/.315/.367 with 14 home runs and 64 RBI in a minus-0.8 WAR season in 2009, and he was released the following May. To make matters worse, he caught on with the San Francisco Giants and posted a 136 OPS+ with 18 home runs and 51 RBI in 96 games while the Rays were paying his salary.

Runner-Up: DH Manny Ramirez (Jan. 31, 2011)

Date: Jan. 16, 2002
Contract: Five years, $65 million

In the five seasons with the Los Angeles Dodgers leading up to his free agency, Chan Ho Park posted a 3.79 ERA, 108 ERA+ and 966 strikeouts in 1,067 innings while tallying 15.8 WAR in 165 starts.

The Texas Rangers paid a steep price in hopes of him shoring up a starting rotation that was consistently in flux during the 1990s and 2000s, but he struggled from the start in Arlington. In three and a half seasons with the team, he had a 5.79 ERA and 1.61 WHIP in 380.2 innings before he was traded to the San Diego Padres for Phil Nevin.

Runner-Up: OF Juan González (Jan. 8, 2002)

Date: Nov. 29, 2005
Contract: Five years, $47 million

Left-hander B.J. Ryan had quality seasons in 2006 (65 G, 38 SV, 1.37 ERA, 10.7 K/9) and 2008 (60 G, 32 SV, 2.95 ERA, 9.0 K/9), but he made just five appearances in 2007 and struggled to a 6.53 ERA in 25 appearances in 2009.

The Blue Jays ultimately released him midway through the fourth year of his contract and he didn't pitch again at the MLB level. In the end, they paid $47 million for 75 saves and 3.8 WAR in 155 appearances.

Runner-Up: SP Tanner Roark (Dec. 18, 2019)

Date: Dec. 9, 2019
Contract: Seven years, $245 million

After going 18-6 with a 3.32 ERA, 1.04 WHIP and 251 strikeouts in 209 innings during the 2019 season, Stephen Strasburg won World Series MVP honors while leading the Washington Nationals to a title.

The Nationals chose to let Anthony Rendon walk in free agency that offseason while bringing Strasburg back on one of the richest contracts ever given to a pitcher. While he has three years and $105 million left on his contract, the expectation is that he will never pitch again.

That means the Nationals will have paid $245 million for eight total starts, during which time he went 1-4 with a 6.89 ERA and 1.56 WHIP in 31.1 innings. He will have made $1.7 million for every batter he faced.

Runner-Up: SP Patrick Corbin (Dec. 7, 2018)