Every MLB Team's Biggest Free-Agent Flop of the Last Decade
For over 40 years, Major League Baseball's free-agent system has had its benefits for teams and especially for players.
It's not exactly uncommon, though, for teams to come to rue especially expensive contracts.
To illustrate, we've pinpointed each team's biggest free-agent regret of the last decade. We drew the line at deals signed before the 2011 season, and they must have been worth at least $20 million over at least two years. From there, we narrowed things down to the biggest deal that generated the least on-field value.
We'll proceed in alphabetical order by city.
Arizona Diamondbacks: OF Yasmany Tomas
1 of 30
Terms: 6 Years, $68.5 Million
WAR: Minus-2.5
One year in, the Arizona Diamondbacks' five-year, $85 million deal with Madison Bumgarner is already looking like a tremendous mistake.
Because of a back strain, the former San Francisco Giants ace made only nine starts for Arizona in 2020. He also struggled with a 6.48 ERA and greatly reduced velocity that hints at further trouble to come.
For now, however, Yasmany Tomas stands alone among Arizona's worst free-agent misfires.
He was supposed to be their Jose Abreu when they signed him in December 2014, but he turned out to be a deeply flawed hitter (i.e, a .306 OBP) whose value was further sunk by his limited athleticism. The Snakes basically gave up on him after 2017 as he appeared in only four games in the final three years of his deal.
Atlanta: OF Melvin Upton Jr.
2 of 30
Terms: 5 Years, $75.3 Million
WAR: Minus-1.7
Even at the time it was struck in November 2012, Atlanta's five-year deal with Melvin Upton Jr. seemed reckless.
Upton had enjoyed some good seasons for the Tampa Bay Rays, including a 2007 campaign in which he hit .300 with 24 home runs and 22 stolen bases. But he'd mostly been inconsistent and was coming off a 2012 season marked by an alarmingly low .298 OBP.
Upton only got worse with Atlanta. He hit just .198 with a .279 OBP across the 2013 and 2014 seasons, striking out in 31.5 percent of his plate appearances.
Ultimately, Atlanta jettisoned Upton by packaging him with ace closer Craig Kimbrel in a trade with the San Diego Padres in April 2015. Though his contract ran through 2017, he played his last major league game in October 2016.
Baltimore Orioles: 1B Chris Davis
3 of 30
Terms: 7 Years, $161 Million
WAR: Minus-3.3
The Baltimore Orioles weren't completely out of their minds when they re-signed Chris Davis to a nine-figure deal in January 2016.
He had been the major league home run leader in two of the last three seasons, launching 53 blasts in 2013 and 47 in 2015. And this was when home runs were generally scarce as even a surge in homers during the second half of 2015 only pushed the league's final average to 1.01 per game.
Still, Davis wouldn't have much to fall back on if his power eventually dried up. That's precisely what's happened over the last four seasons, wherein he's hit just .185 and produced minus-6.4 WAR.
Unfortunately for the Orioles, Davis' deal still has two years left on it. Meanwhile, home runs are now more common than they've ever been.
Boston Red Sox: 3B Pablo Sandoval
4 of 30
Terms: 5 Years, $95 Million
WAR: Minus-1.6
The Boston Red Sox have certainly had some stinkers in free agency, including their seven-year, $142 million deal with Carl Crawford from December 2010.
Yet the Crawford deal didn't actually end up hurting Boston that much. Though he produced only 0.9 WAR in 161 games for them, the Red Sox got out of his contract when they sent him to the Los Angeles Dodgers in August 2012.
By comparison, Boston's experience with Pablo Sandoval was far worse.
Chicago Cubs: SP Edwin Jackson
5 of 30
Terms: 4 Years, $52 million
WAR: Minus-3.5
Five seasons in, it's fair to call Jason Heyward's eight-year, $184 million contract with the Chicago Cubs a disappointment.
Just don't call it a flop. Heyward has won two Gold Gloves and posted a non-terrible 8.4 WAR with the Cubs, and the team's victory in the 2016 World Series may not have happened if he hadn't rallied the troops in Game 7.
Compare that with the whole lot of nothing the Cubs got out of Edwin Jackson.
He wasn't much more than an innings-eater even when the Cubs signed him in January 2013. He couldn't even be that for them, pitching to a 5.37 ERA and making 24 of his 82 appearances with the club out of the bullpen. The Cubs released him halfway through the third year of his deal.
Chicago White Sox: DH Adam Dunn
6 of 30
Terms: 4 Years, $56 Million
WAR: Minus-0.4
Between 2004 and 2010, few sluggers were as consistent as Adam Dunn. He averaged 40 home runs in that span, in which he never dipped below 38 homers in a season.
Upon joining the Chicago White Sox in December 2010, Dunn promptly had one of the worst seasons in MLB history. Though he played in 122 games in 2011, he hit just .159 with 11 homers and minus-2.9 WAR.
To his credit, Dunn rebounded in 2012 with an All-Star effort marked by 41 homers. But he couldn't live up to that standard in 2013 and 2014, the latter of which saw him finish the year with the Oakland Athletics following an August trade.
After 14 seasons, Dunn promptly called it quits with 462 home runs yet only 18.0 WAR to his name.
Cincinnati Reds: RHP Jonathan Broxton
7 of 30
Terms: 3 Years, $21 Million
WAR: 1.1
Though the Cincinnati Reds' $64 million pacts with Nick Castellanos and Mike Moustakas from last offseason didn't yield much value in 2020, it's a bit soon to render final judgment on either deal.
The deal Cincinnati struck with Jonathan Broxton in November 2012 is our only other option, so it's a good thing for us that it didn't work out.
The Reds originally teamed up with Broxton in a trade with the Kansas City Royals in July 2012. He went on to post a 2.82 ERA in 25 appearances, helping the Reds win the National League Central title.
But in 2013, Broxton lost time with an elbow strain and struggled with a 4.11 ERA when he could pitch. As soon as he regained value in 2014, the Reds dumped his remaining contract on the Milwaukee Brewers.
Cleveland: OF/1B Nick Swisher
8 of 30
Terms: 4 Years, $56 Million
WAR: 1.1
Following a 94-loss season in 2012, Cleveland made an aggressive play to return to contention by hiring Terry Francona as its manager and spending $104 million on Nick Swisher (here) and Michael Bourn (here).
It worked. Swisher and Bourn put up solid numbers in 2013 while Francona guided the team with a steady hand en route to 92 wins and a playoff berth.
However, it was all downhill for Swisher and Bourn after 2013—particularly for the former, who mustered only a .608 OPS in 2014 and a .558 OPS in just 30 games for Cleveland in 2015.
August 2015 marked the end of the road for both Swisher and Bourn with Cleveland, which sent them to Atlanta in a bad-contract-swap involving Chris Johnson.
Colorado Rockies: OF Ian Desmond
9 of 30
Terms: 5 Years, $70 Million
WAR: Minus-3.2
After what they went through with Wade Davis ($52 million), Jake McGee ($27 million) and Bryan Shaw ($27 million), it might be a while before the Colorado Rockies spend big bucks on a reliever again.
But if they could have a do-over on any of their recent contracts, they'd surely choose Ian Desmond.
Desmond's deal seemed doomed to fail as soon as it was made in December 2016. He owned an exactly average 100 OPS+ to that point in his career. And whereas he had experience at shortstop and center field, the Rockies planned on using him at first base.
Still, nobody could have expected Desmond to be the worst player in the National League between 2017 and 2019. After sitting out the 2020 season, it'll take a monumental effort for him to redeem his contract in 2021.
Detroit Tigers: SP Jordan Zimmermann
10 of 30
Terms: 5 Years, $110 Million
WAR: 1.1
After reigning as American League Central champions each year between 2011 and 2014, the Detroit Tigers took a step back and lost 87 games in 2015.
As part of their effort to get back on track, the Tigers signed Jordan Zimmermann in December 2015. Given that he had pitched at an All-Star level for the Washington Nationals over the five previous seasons, it seemed like a safe enough maneuver.
Not so much, as it turned out.
In five seasons with Detroit, Zimmermann battled both diminished velocity and a handful of injuries as he posted a 5.63 ERA in 99 appearances. For their part, the Tigers missed the playoffs once again in 2016 and were so hopeless by 2017 that they had little choice but to enter into a rebuild.
Houston Astros: SP Scott Feldman
11 of 30
Terms: 3 Years, $30 Million
WAR: 3.0
Despite all their recent success, the Houston Astros haven't been particularly aggressive in free agency over the last decade.
They've done only three deals with multiple years and at least $20 million in guaranteed money. The richest of those was their four-year, $52 million pact with Josh Reddick in November 2016, which initially resulted in one very good season for both sides in 2017.
As such, we have little choice but to pick on Scott Feldman here.
Though they were still in the process of rebuilding, the Astros signed Feldman in January 2014 because they needed someone to eat innings. He did that just fine with a 3.74 ERA over 180.1 frames in 2014. But his durability slipped in 2015, and the Astros ultimately traded him to the Toronto Blue Jays in August 2016.
Kansas City Royals: 2B Omar Infante
12 of 30
Terms: 4 Years, $30.3 Million
WAR: Minus-0.6
The Kansas City Royals stretched their budget to do $70 million deals with both Alex Gordon (here) and Ian Kennedy (here) in January 2016. Neither panned out as well as the club hoped.
The Royals did, however, get a lot more out of both Gordon and Kennedy than they did out of Omar Infante.
When the Royals nabbed Infante in December 2013, they were pairing up with a generally reliable second baseman who was fresh off one of his finest seasons. Albeit in only 118 games, he had hit a solid .318 for the Detroit Tigers in '13.
Instead, what the Royals got was the out-of-gas version of Infante. He hit just .238 with eight home runs in 298 games between 2014 and 2016, ultimately earning his release in June of the latter year.
Los Angeles Angels: OF Josh Hamilton
13 of 30
Terms: 5 Years, $125 Million
WAR: 2.7
Let's talk about Albert Pujols for a second.
We're not about to suggest the Los Angeles Angels have gotten their money's worth out of the 10-year, $240 million deal they signed with Pujols back in December 2011. But given that he's produced 217 home runs and 13.9 WAR, we will propose that it hasn't been a total disaster.
Instead, consider the actual disaster that was the Angels' deal with Josh Hamilton.
Hamilton was riding a string of five straight All-Star seasons when the Angels signed him in December 2012, but his offensive production dried up as he managed just a .741 OPS in 240 games across the 2013 and 2014 campaigns. And when the Angels traded him to the Texas Rangers in April 2015, they recouped only $20 million from their initial investment.
Los Angeles Dodgers: SP Brandon McCarthy
14 of 30
Terms: 4 Years, $48 Million
WAR: 0.4
Though Hector Olivera's six-year, $62.5 million contract is one of the biggest blunders in recent memory, the Los Angeles Dodgers got out of it well before it went south.
Andrew Friedman has nonetheless had other misfires since taking over the club's front office in 2014. These include big-money deals with relievers Kenley Jansen ($80 million) and Joe Kelly ($25 million) that are still ongoing.
Also on Friedman's record are $48 million contracts with Brandon McCarthy and Scott Kazmir, the latter of whom produced just enough WAR (0.5) to avoid our less-than-flattering spotlight.
Miami Marlins: SP Wei-Yin Chen
15 of 30
Terms: 5 Years, $80 Million
WAR: Minus-0.6
Whenever Bruce Sherman and Derek Jeter spend big in free agency, they can only do better than the Miami Marlins' previous owner.
As embarrassments go, it's hard to top what became of the $191 million worth of contracts Jeffrey Loria dished out to Jose Reyes, Mark Buehrle and Heath Bell in December 2011. They were meant to usher in a new era of Marlins baseball. Instead, the 2012 club flopped, and all three players were promptly traded.
But as far as singular flops are concerned, there's no topping Wei-Yin Chen.
Milwaukee Brewers: SP Matt Garza
16 of 30
Terms: 4 Years, $50 Million
WAR: Minus-0.7
The Milwaukee Brewers have done only two free-agent deals worth more than $50 million. One is their ongoing five-year, $80 million pact with Lorenzo Cain, which has been a worthy investment.
And then there's the deal that the Brewers made with Matt Garza in January 2014.
Even at the time, whether Garza was worthy of a $50 million contract was debatable. He'd had a couple years with the Tampa Bay Rays and Chicago Cubs in which he was good for 200 above-average innings. But in 2012 and 2013, he had pitched to good-not-great 3.86 ERA over 259 total innings.
Though he did post a solid 3.64 ERA in 2014, Garza only logged 163.1 innings that year. The following three years were no better, as he made only 66 starts and struggled with a 5.10 ERA.
Minnesota Twins: SP Ricky Nolasco
17 of 30
Terms: 4 Years, $49 Million
WAR: Minus-0.1
One year in, the Minnesota Twins might be feeling nervous about their four-year, $92 million deal with Josh Donaldson.
To be fair, he did post a respectable .842 OPS while he was healthy in 2020. But he was healthy for only 28 of the club's 60 games, as he spent significant time on the injured list with a calf strain for the third time in the last four seasons.
But at least until Donaldson declines any further, Ricky Nolasco still stands alone as the worst signing in Minnesota's recent history.
New York Mets: INF Jed Lowrie
18 of 30
Terms: 2 Years, $20 Million
WAR: Minus-0.2
This is where it's hard to settle on only one bad contract, because the New York Mets' recent history with big-money free-agent deals is...not great.
For instance, they inked Yoenis Cespedes to a $110 million contract in November 2016 only to watch him succumb to numerous injuries. In January 2018, they signed Jay Bruce for $39 million and watched him post minus-1.0 WAR in '18 before they pulled the plug that winter.
But hey, at least Cespedes and Bruce played for the Mets. One can barely say the same about Jed Lowrie.
Lowrie was coming off two quality years with the Oakland Athletics when he signed with the Mets in January 2019. But then the injury bug came for him, ultimately allowing him to take only seven at-bats in just nine games in a Mets uniform.
New York Yankees: OF Jacoby Ellsbury
19 of 30
Terms: 7 Years, $153 Million
WAR: 9.7
When the New York Yankees signed Jacoby Ellsbury away from the Red Sox in December 2013, they were hoping to get one of two possible versions of him.
They would ideally get the MVP-caliber version of Ellsbury from 2011, when he went off for a .928 OPS with 32 homers and 39 stolen bases. Failing that, something more like the 2013 Ellsbury—who stole 52 bases from atop the lineup of a World Series-winning team—would do.
As it turned out, the Yankees got neither version of Ellsbury.
Though he was solid with a .747 OPS, 16 homers and 39 steals in 2014, subsequent seasons saw Ellsbury's offensive skills diminish and his durability fall apart. He didn't play at all in 2018 or 2019, and was subsequently released with a year still left on his contract.
Oakland Athletics: DH Billy Butler
20 of 30
Terms: 3 Years, $30 Million
WAR: Minus-0.6
Why the heck the Oakland Athletics signed Billy Butler remains one of baseball's great mysteries.
This is, after all, a team that typically doesn't spend much in free agency. That's partially a function of the organization always operating with low payrolls, and partially of a front office that's equal parts creative and cautious.
In theory, such a front office should have wanted nothing to do with Butler after the year he'd had with the Royals in 2014. He played in 151 games, but posted just a .702 OPS and nine homers.
Philadelphia Phillies: SP Jake Arrieta
21 of 30
Terms: 3 Years, $75 Million
WAR: 4.4
The Philadelphia Phillies' 13-year, $330 million pact with Bryce Harper has started strong, as the 2015 NL MVP has thus far graced them with a .903 OPS and 48 homers in two seasons.
Otherwise, relatively little of the money that the Phillies have spent in free agency recently has been well spent. In particular, they never really got what they were hoping for out of Jake Arrieta.
When the Phillies signed Arrieta in March 2018, he was only three years removed from winning the NL Cy Young Award with the Cubs in 2015. Diminishing returns in 2016 and 2017, however, raised the possibility that his prime was behind him.
Unfortunately for the Phillies, that turned out to be true. Arrieta never resembled his ace-like self for them, posting just a 4.36 ERA in 64 starts.
Pittsburgh Pirates: SP Francisco Liriano
22 of 30
Terms: 3 Years, $39 Million
WAR: 2.1
The Pittsburgh Pirates don't do many free-agent deals in general, much less ones worth tens of millions of dollars over multiple years.
Indeed, we had only two options for this exercise: Pittsburgh's three-year, $39 million deal with Francisco Liriano from December 2014, or its three-year, $26 million contract with Ivan Nova from December 2016.
Neither of those deals truly backfired on the Pirates, but Liriano's was ultimately less fruitful.
Liriano pitched to an excellent 3.38 ERA over 186.2 innings in 2015, but promptly fell from grace in 2016 and was traded to the Toronto Blue Jays in August. For his part, Nova put up a 4.16 ERA over 60 starts between 2017 and 2018 before he was also moved.
San Diego Padres: 1B Eric Hosmer
23 of 30
Terms: 8 Years, $144 Million
WAR: 2.1
The San Diego Padres broke their mold when they signed James Shields to a $75 million contract in February 2015, and they didn't let themselves come to regret it.
After a solid first season in San Diego, the Padres ducked the looming end of Shields' prime when they dealt him to the White Sox in June 2016. The centerpiece of that deal was none other than Fernando Tatis Jr.
If there was a time for the Padres to pull a similar trick by trading Eric Hosmer, it may have already passed.
Even though Hosmer showed signs of life with an .851 OPS in 2020, he also played in only 38 games and mustered just 0.9 WAR. With the bar set at 300 games, he now ranks 106th out of 117 position players in WAR since 2018.
San Francisco Giants: RHP Mark Melancon
24 of 30
Terms: 4 Years, $62 Million
WAR: 0.8
Even in retrospect, it's hard to blame the San Francisco Giants for going all-in on Mark Melancon in December 2016.
They were still a contender at the time, having earned their fourth postseason berth in seven seasons in 2016. Yet they didn't have the most reliable bullpen during the '16 season, so why not sign the guy who had accumulated a 1.80 ERA and the most WAR of any reliever between 2013 and 2016?
Alas, Melancon was just never that guy for the Giants.
Seattle Mariners: SP Yusei Kikuchi
25 of 30
Terms: 4 Years, $56 Million
WAR: 0.6
It's a good look for the Seattle Mariners that their two biggest free-agent deals of the last decade both panned out well.
For $56 million over four years, Nelson Cruz gave the Mariners a .908 OPS and 163 home runs. After inking a 10-year, $240 million deal in December 2013, Robinson Cano racked up 23.3 WAR in four seasons before the Mariners sent him to the Mets in a deal that brought back uber-prospect Jarred Kelenic.
Seattle's pact with Yusei Kikuchi, on the other hand, isn't going so great.
Since signing with Seattle in January 2019, he's thus far fallen flat with a 5.39 ERA in 41 outings. Though his contract is only guaranteed through 2021, he's all but certain to collect another $13 million via a player option for 2022.
St. Louis Cardinals: OF Dexter Fowler
26 of 30
Terms: 5 Years, $82.5 Million
WAR: 2.0
Similar to the Mets, the St. Louis Cardinals made it hard for us to pick just one bad contract for this list.
Since 2013, they've done deals of at least two years and $20 million with Jhonny Peralta, Mike Leake, Brett Cecil, Dexter Fowler and Andrew Miller. Frankly, none of them has paid the kind of dividends the Cardinals were hoping for.
We're singling out Fowler, however, because his deal is the biggest of the bunch and because there's very little hope of the 34-year-old ending it on a strong note in 2021.
Even Fowler's best year (2017) as a Cardinal yielded only 1.8 WAR. He's otherwise spent most of his time in St. Louis battling injuries and slumps, with his most recent effort being a .706 OPS in 31 games in 2020.
Tampa Bay Rays: 1B James Loney
27 of 30
Terms: 3 Years, $21 Million
WAR: 0.4
The Tampa Bay Rays have done only two deals in free agency in which they guaranteed at least $20 million over at least two years.
The more recent of those was their two-year, $30 million contract with Charlie Morton from December 2018. It suffices to say that went well, as he placed third in the AL Cy Young Award voting in 2019 and helped lead a run to the World Series this past season.
If only the pact that the Rays made with James Loney in January 2014 had turned out as well.
After a solid effort in 2013 marked by a .778 OPS and 13 homers, Loney managed only a .703 OPS and 13 total homers across the 2014 and 2015 campaigns. The Rays released him on the eve of the 2016 season.
Texas Rangers: RF/DH Shin-Soo Choo
28 of 30
Terms: 7 Years, $130 Million
WAR: 8.4
In fairness to the Texas Rangers, their recent history in free agency offers few obvious misfires.
They haven't been quick to spend big money, and it's generally worked out well when they have. For instance, take their massive score on Adrian Beltre ($80 million) and their lesser, yet still significant score on Mike Minor ($28 million).
Because it's too soon to rag on Texas' three-year, $28 million deal with Kyle Gibson, we therefore have no choice but to nitpick their pact with Shin-Soo Choo from December 2013.
Because he stayed on the field for 799 games and even made an All-Star team in 2018, Choo's deal was hardly a disaster for the Rangers. But considering that he provided little to no defensive value, his .260 average and .792 OPS were ultimately disappointing offensive numbers.
Toronto Blue Jays: DH Kendrys Morales
29 of 30
Terms: 3 Years, $33 Million
WAR: 0.8
The Toronto Blue Jays are another team whose recent free-agent activity offers little to complain about.
To wit, Russell Martin helped anchor playoff teams in 2015 and 2016 after signing an $82 million deal with Toronto in November 2014. The Jays took a similar risk when they inked Hyun Jin Ryu for $80 million last December, but he responded by finishing third in the AL Cy Young Award voting for 2020.
Heck, even the deal that Kendrys Morales signed in November 2016 didn't go that terribly for Toronto. It's just that—and this is us shrugging—it didn't go that great either.
Though Morales hit 49 home runs in 2017 and 2018, he did so with a modest .760 OPS. The Jays promptly gave up on him when they dealt him to Oakland in March 2019.
Washington Nationals: C Matt Wieters
30 of 30
Terms: 2 Years, $21 Million
WAR: Minus-0.4
Because he produced only 9.0 WAR while serving out a seven-year, $126 million contract with the Washington Nationals, Jayson Werth arguably deserves a finger-wagging here.
But while Werth may not have been the most consistent producer, he played well enough to earn MVP votes in 2013 and 2014. And in general, he was one of the key leaders on postseason clubs in 2012, 2014, 2016 and 2017.
Washington's recent free-agent history is otherwise littered with success stories, covering both larger (Max Scherzer and Patrick Corbin) and smaller (Daniel Murphy, Adam LaRoche and Rafael Soriano) contracts.
So, Matt Wieters gets the finger-wagging by default. He was coming off an All-Star season when the Nats signed him in February 2017, yet his two seasons in Washington yielded only a .658 OPS and unspectacular defense.
Stats courtesy of Baseball Reference and FanGraphs.
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