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The Boston Red Sox’s $95 million bet on Pablo Sandoval didn’t turn out so well.Patrick Semansky/Associated Press
Free-agent success stories are more common in Major League Baseball than you might think, but teams know all too well that failures can and do happen.
There are plenty of examples from the last 20 years.
We’ve highlighted what we think is each team’s worst free-agent signing since 2000. This naturally involved hunting for non-extension multiyear contracts that paid out big bucks—i.e., a minimum of $10 million—to players who didn’t produce much on the field.
However, we didn’t simply go looking for the largest disparity between dollars paid out and value generated. A methodology such as that would have pointed us in the direction of merely disappointing signings, whereas we were looking for total flops.
We’ll proceed in alphabetical order by city.
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Jennifer Stewart/Getty Images
Date: December 9, 2014
The Deal: Six years, $68.5 million
From one perspective, the Arizona Diamondbacks’ signing of Yasmany Tomas is Jose Abreu’s fault.
The Chicago White Sox took a chance when they signed Abreu to a six-year, $68 million contract in October 2013. After he dominated en route to winning the American League Rookie of the Year in 2014, the D-backs might have figured they couldn’t lose a big bet of their own on a fellow Cuban defector that winter.
But to overcome his athletic limitations, Tomas was going to have to hit. To this end, he disappointed with a .769 OPS through his first 305 games in the majors. After a core muscle injury in 2017, Arizona banished him to the minors in 2018, and he didn’t resurface in the majors until last July.
In August, the Diamondbacks outrighted Tomas off their 40-man roster. However, he won’t finally be off their payroll until after this season.
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R. Yeatts/Getty Images
Date: November 29, 2012
The Deal: Five years, $75.25 million
The Atlanta Braves typically aren’t associated with big free-agent signings, so it was surprising when they inked Melvin Upton Jr.
Even more puzzling was the reality that the Braves went hard after Upton even though he wasn’t coming off a particularly good season. Though he had tallied 28 home runs and 31 stolen bases for the Tampa Bay Rays in 2012, he also finished with a .298 on-base percentage and 2.7 WAR.
Still, nobody could have expected that Upton would crash as hard as he did. He endured a mighty offensive struggle in 2013 and 2014 that was marked by a .198/.279/.314 slash line.
The Braves jettisoned Upton by dealing him to the San Diego Padres in April 2015. But because they had to package him with ace closer Craig Kimbrel, the deal was effectively a salary dump.
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Julio Cortez/Associated Press
Date: January 21, 2016
The Deal: Seven years, $161 million
The Baltimore Orioles’ deal with Chris Davis is by far the most they’ve ever paid out to a single player. In fact, it’s about twice as much as Adam Jones’ $85.5 million extension from 2012.
At the time, Baltimore’s pact with Davis was reasonably defensible. He was coming off his second home run title in three seasons, and they weren’t altogether finished as contenders in the American League East.
In four years since then, however, both player and team have deteriorated. Davis’ bat has produced just a .679 OPS and 92 home runs. The Orioles made the playoffs in 2016, but slipped to 87 losses in 2017 and then to 223 losses across the 2018 and 2019 seasons.
Because of the shortened season, the Orioles will save some money on Davis’ $23 million salary for 2020. But unless he retires, they’ll still owe him $46 million for 2021 and 2022.
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Michael Dwyer/Associated Press
Date: November 25, 2014
The Deal: Five years, $95 million
After signing Crawford, the Red Sox avoided big splashes in free agency until the winter of 2014-15. In hopes that they would elevate the team after a 91-loss season, the Red Sox dropped $183 million on Pablo Sandoval and Hanley Ramirez.
By contrast, nothing ever went right for Sandoval in Boston. He played in only 161 games over three seasons and hit just .237 with a .646 OPS before he was finally released in July 2017.
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Jonathan Daniel/Getty Images
Date: January 2, 2013
The Deal: Four years, $52 million
The Chicago Cubs haven’t gotten what they hoped for out of Jason Heyward, who they signed for $184 million over eight years in December 2015.
Edwin Jackson, meanwhile, was supposed to still be around to hear Heyward’s speech. Trouble is, he didn’t make it to the end of his four-year contract with the Cubs.
Because they were still rebuilding and Jackson was coming off a modest 4.03 ERA for the Washington Nationals in 2012, the sides were an odd pairing to begin with. He eventually put up a 5.37 ERA in 82 appearances for Chicago through July 2015 and was promptly shown the door.
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Jim McIsaac/Getty Images
Date: December 3, 2010
The Deal: Four years, $56 million
Adam Dunn pretty much did a 180 upon joining the Chicago White Sox ahead of the 2011 season.
He joined them off a productive campaign with the Washington Nationals in 2010, wherein he mustered an .892 OPS with 38 home runs and 2.5 WAR. But disaster struck in his first season on the South Side, as he finished 2011 with only 11 home runs and minus-2.9 WAR. The latter is a rare figure for position players.
To his credit, Dunn recovered with 41 blasts and his second All-Star selection in 2012. But his power was really all he had by then, and it gradually diminished in 2013 and 2014.
Dunn ended the ’14 season with the Oakland Athletics but didn’t make it into their loss to the Kansas City Royals in the AL Wild Card Game. He called it a career without ever having played in the postseason.
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Joe Robbins/Getty Images
Date: December 10, 2012
The Deal: Two years, $15 million
Up until they signed Nicholas Castellanos and Mike Moustakas for $64 million apiece, the Cincinnati Reds’ biggest free-agent deal was a $46 million pact with closer Francisco Cordero that turned out quite well.
As such, Ryan Ludwick is HERE because there’s really nobody else to pick on.
To clarify, he signed with the Reds as a free agent on two different occasions. The first was via a one-year, $2.5 million deal that resulted in a rock-solid .877 OPS and 26 home runs in 2012. After that, it’s little wonder that the Reds wanted to continue their partnership with Ludwick.
But this time, they weren’t so fortunate. Ludwick played in only 38 games in 2013, and he was never seen in the majors again after finishing 2014 with a .683 OPS and nine homers.
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Jason Miller/Getty Images
Date: January 3, 2013
The Deal: Four years, $56 million
The Cleveland Indians have yet to go beyond even $60 million in any free-agent deal, and the one time they hit that mark netted them a couple of solid seasons from Edwin Encarnacion.
The Indians did, however, make a $104 million splash when they signed Nick Swisher ($56 million) and Michael Bourn ($48 million) within weeks of each other in 2013. And it initially worked, as both played roles in getting the Tribe to the playoffs that year.
But neither had much left after 2013. And both eventually took the same bus out of town when the Indians dumped them on the Atlanta Braves in August 2015.
Between the two, we’re harping on Swisher because he fell much harder after debuting in Cleveland with 3.7 WAR in 2013. Injuries and a power outage sent him well below the replacement-level threshold in his last season-and-a-half with the Indians.
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David Zalubowski/Associated Press
Date: December 13, 2016
The Deal: Five years, $70 million
In December 2000, the Colorado Rockies made a $121 million deal with Mike Hampton that famously didn’t pan out. But hey, at least they got future All-Star Preston Wilson in the trade that sent Hampton out of town in November 2002.
By now, it’s clear the Rockies won’t be so lucky with Ian Desmond.
Even when the two first joined forces after the 2016 season, the whole thing had an “Are you sure about this?” vibe to it. Desmond was fresh off a bad second-half slump for the Texas Rangers. The Rockies were also planning on playing him at first base, a position with which he was unaccustomed.
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Paul Sancya/Associated Press
Date: November 30, 2015
The Deal: Five years, $110 million
In retrospect, the Detroit Tigers’ nine-year, $214 million deal with Prince Fielder in January 2012 is one of the biggest miscalculations in recent memory.
The Tigers did, however, calculate correctly when they traded Fielder to the Texas Rangers less than two years later in November 2013. They got out of the bulk of his remaining contract and even got Ian Kinsler, who still had some good seasons left, in return.
If only the Tigers could find a similar way to get out of Jordan Zimmermann’s contract.
Though he had been an All-Star for the Washington Nationals in 2013 and 2014, his velocity was already in decline when the Tigers signed him in 2015. That decline has continued, and Zimmermann has also had trouble with injuries while racking up a 5.61 ERA in four seasons with Detroit.
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Gene J. Puskar/Associated Press
Date: November 24, 2006
The Deal: Six years, $100 million
The big problem with a given free-agent signing doesn’t always concern the production that followed. Sometimes, it’s the intent.
To wit, the Houston Astros were basically calling a Hail Mary when they signed Carlos Lee to a nine-figure deal in 2006. Sure, they had gone to the World Series in 2005. But they had won only 82 games in 2006, and there they were adding an aging slugger to an aging roster.
Lee did his part to the right the proverbial ship in 2007—his age-31 season—posting an .882 OPS with 32 homers. He continued to hit well in 2008 too. But it was for naught as the Astros missed the playoffs in both of those years.
Come 2009, both Lee and the Astros were past their primes. He eventually went to the Miami Marlins via trade in July 2012, and they didn’t get their act together again until 2015.
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Harry How/Getty Images
Date: December 4, 2007
The Deal: Three years, $36 million
In hindsight, the unprecedented $142 million investment that the Kansas City Royals made in Alex Gordon ($72 million) and Ian Kennedy ($70 million) after their World Series win in 2015 doesn’t look great.
However, it’s also not as big of a disaster as you might think. Though his offense dried up, Gordon at least won Gold Gloves in 2017, 2018 and 2019. For his part, Kennedy had a solid year as a starter in ’16 and is now a pretty good closer.
Though it was for roughly half as much money as both, the Royals’ deal with Jose Guillen in 2007 turned out far worse.
Guillen was a notoriously volatile performer even before arriving in Kansas City, and he failed to find consistency as he was putting up a .727 OPS in his two-and-a-half seasons with the team. The experiment finally ended when the Royals flipped him to the San Francisco Giants in August 2010.
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Rob Carr/Associated Press
Date: November 22, 2006
The Deal: Five years, $50 million
Albert Pujols’ 10-year, $240 million contract was never a good deal for the Los Angeles Angels, but it’s only recently that it’s become a truly bad pact.
His first four years in Anaheim were marked by 13.3 WAR, 115 home runs and an All-Star nod in 2015. He’s now in sunk-cost territory with 0.9 WAR since 2016, but no amount of additional crumbling in 2020 and 2021 will totally undo those first four seasons.
Besides, at least the Angels had the right idea in signing Pujols in 2010. The opposite was true when they signed Gary Matthews four years earlier.
His breakout season with the Texas Rangers in 2006 was an obvious outlier, and he was heading into his age-32 season. It was therefore no big surprise when Matthews flopped in Anaheim, and the Angels didn’t save much money when they traded him to the New York Mets in 2010.
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Rob Leiter/Getty Images
Date: December 6, 2006
The Deal: Three years, $47 million
Otherwise, the Dodgers’ recent free-agent signings have mostly worked out. That could change, depending on how Kenley Jansen and A.J. Pollock trend after difficult years in 2019, but it’s too soon to declare either a bust.
As such, we have little choice but to go all the way back to that time the Dodgers signed Jason Schmidt only to get next to nothing out of him.
Largely because of injuries, Schmidt ended up making only 10 starts and posting a 6.02 ERA from 2007 to 2009. Why the Dodgers expected better is a good question, as Schmidt was in his mid-30s and clearly past his prime when they signed him.
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John Minchillo/Associated Press
Date: January 19, 2016
The Deal: Five years, $80 million
Remember when the Miami Marlins spent $191 million on Jose Reyes, Mark Buehrle and Heath Bell in 2011, only to trade all three after a 93-loss season in 2012?
That was a bad look for the franchise at the time, and it would be best for baseball if no other team trafficked in that much cynicism ever again.
Yet despite all this, we still have a hard time seeing Wei-Yin Chen as anything other than the worst free-agent signing the Marlins have ever made. He was often hurt in his four years in Miami and ineffective when he wasn’t. All told, he posted a 5.10 ERA in 102 appearances.
And unlike Reyes, Buehrle and Bell, the Marlins couldn’t get out of paying Chen. Albeit at a reduced rate amid the shortened season, he’s still on their books.
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Morry Gash/Associated Press
Date: December 24, 2006
The Deal: Four years, $42 million
It may be a while before the Milwaukee Brewers go bigger in free agency than the five-year, $80 million contract they signed with Lorenzo Cain in 2018. When they do, they’ll be lucky if the dividends are as good.
As it is, it’s perhaps a small miracle that the Brewers weren’t scared away by the two biggest free-agent deals they made before signing Cain: $42 million for Jeff Suppan in 2006 and $50 million for Matt Garza in 2014.
Coincidentally, both right-handers marked their four seasons in Milwaukee by pitching to exactly (see here for Garza) minus-0.7 WAR. But whereas Garza had an above-average 104 ERA+ in ’14, Suppan never rose to that level from 2007 to 2010.
What’s more, $42 million was a lot for a pitcher in those days. To that point, only Suppan and five other pitchers had hit that mark in free agency.
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Hannah Foslien/Getty Images
Date: December 3, 2013
The Deal: Four years, $49 million
The Minnesota Twins blew away their previous record for a free-agent payout when they signed Josh Donaldson to a four-year, $92 million contract in January.
May that deal pan out better than the four-year pact they signed with Ricky Nolasco in 2013.
At the time, Nolasco seemed to be a good value play for the Twins. He came free of draft-pick compensation, and was fresh off a 3.70 ERA over 199.1 innings with the Miami Marlins and Los Angeles Dodgers. Any more of that, and he’d help the Twins climb up the ranks in the AL Central.
That didn’t happen. Nolasco pitched to a 5.44 ERA in just 57 appearances through August 2016, when the Twins finally gave up and sent him to the Los Angeles Angels.
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Kathy Kmonicek/Associated Press
Date: December 29, 2009
The Deal: Four years, $66 million
The New York Mets have done some bad deals in free agency, the most recent of which happened less than four years ago when they re-signed Yoenis Cespedes for four years and $110 million.
But on balance, that contract hasn’t been a total catastrophe. Cespedes hit well in the 119 games he played in 2017 and 2018. And after he missed all of 2019 because of an oddly acquired injury, the Mets were due to save a good chunk of his 2020 salary even before the season was shortened.
Comparatively speaking, the Mets had a worse time with Jason Bay’s contract.
He was riding a string of four 30-homer seasons in five years when the Mets signed him, but concussions and other health issues contributed to his hitting only 26 homers in three seasons in New York. The result was his release before the 2013 campaign.
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Kathy Willens/Associated Press
Date: December 7, 2013
The Deal: Seven years, $153 million
Given how many hundreds of millions of dollars they have spent on the open market this century, you would think the New York Yankees would be plenty familiar with free-agent duds.
That’s surprisingly not the case. The Yankees have had their share of disappointments, but only their megadeal with Jacoby Ellsbury comes close to being a flat-out bomb.
In fairness, Ellsbury was decent enough in his first season in New York after he jumped ship from the Boston Red Sox following their World Series victory in 2013. He played in 149 games in 2014, finishing with a solid .747 OPS, 16 home runs and 39 stolen bases.
But in the three years after that, Ellsbury really only had his glove to lean on. He was then sidelined by injuries for all of 2018 and 2019, prompting the Yankees to finally release him last November.
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Eric Risberg/Associated Press
Date: November 19, 2014
The Deal: Three years, $30 million
The Oakland Athletics have spent as much as $30 million on a domestic free agent (i.e., not Yoenis Cespedes) only once in their history. Knowing how that turned out, they’re surely in no rush to do it again.
Even at the time, Oakland’s decision to sign Bully Butler to a three-year, $30 million contract was a head-scratcher. He was an All-Star and a Silver Slugger at his peak with the Kansas City Royals, but that had happened two years prior in 2012.
Most recently, Butler had finished the 2014 campaign with a .702 OPS and nine homers. Even amid the dearth of offense that season, it was a subpar offensive output.
Butler did improve to 15 long balls in his first season with the A’s, but his OPS barely budged to .713. After it budged only so slightly to .733 through 85 games in 2016, Oakland cut him loose in September.
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Ross D. Franklin/Associated Press
Date: November 27, 2006
The Deal: Three years, $25.8 million
It’s way too soon to render any kind of fair judgment on the 13-year, $330 million contract that Bryce Harper signed with Philadelphia Phillies last March.
For that matter, it’s also too soon to make a ruling on Jake Arrieta’s three-year, $75 million deal. And while David Robertson’s two-year, $23 million contract is beyond saving, the zero WAR the Phillies have gotten out of him still beats what they got from Adam Eaton back in the day.
Eaton began his major league career as a serviceable yet below-average pitcher for the San Diego Padres from 2000 to 2005. He then went to the Texas Rangers for 2006, in which he managed only a 5.12 ERA in 13 starts.
Looking back, why the Phillies were comfortable handing Eaton a three-year deal is a bigger mystery than how and why he pitched to a 6.10 ERA in two seasons before he was released in 2009.
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Keith Srakocic/Associated Press
Date: December 21, 2016
The Deal: Two years, $11 million
Like the Oakland A’s, the Pittsburgh Pirates typically aren’t big spenders in free agency. Unlike the A’s, they don’t have any obvious bombs in their recent history.
They got one good season out of their three-year, $39 million pact with Francisco Liriano in 2014. They did a three-year, $26 million deal with Ivan Nova two years later, and he was decent over the next two seasons.
This gives us little choice but to pick on Daniel Hudson, who wasn’t even that bad for the Pirates in the one season he spent with the team after signing up for two years in 2016.
He was actually better for the Pirates in 2017 than he had been for the Arizona Diamondbacks in 2016, when he finished with minus-0.5 WAR. And signing him ended up working out for the Pirates, who flipped him to the Tampa Bay Rays for Corey Dickerson ahead of the 2018 season.
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Alex Gallardo/Associated Press
Date: February 19, 2018
The Deal: Eight years, $144 million
It’s only recently that the San Diego Padres have begun flexing their muscles in free agency, most notably with contracts for James Shields, Eric Hosmer and Manny Machado worth $519 million.
Shields’ four-year, $75 million deal from 2015 would have become the worst of those three if the Padres had held on to him. Instead, they pulled off an all-time robbery in June 2016 when they traded him to the Chicago White Sox for Fernando Tatis Jr.
As such, we’re going to jump the gun and single out Hosmer, even though he’s only two seasons into his eight-year, $144 million contract.
He’s been strictly his bad offensive self for the Padres, and the secret is out that he’s a worse defender than his four Gold Gloves would suggest. And now that he’s past 30, he doesn’t offer the hope of youth anymore.
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Dino Vournas/Associated Press
Date: December 29, 2006
The Deal: Seven years, $126 million
Though he would seem like an obvious choice, we’re actually bending our rules to include Barry Zito as the San Francisco Giants’ worst free-agent signing of the 21st century.
His time in San Francisco wasn’t a total loss, after all. He gobbled up more innings than all but 11 National League hurlers from 2007 to 2013. He also helped facilitate the Giants’ championship run in 2012 with two huge starts in the National League Championship Series and the World Series.
Yet even in the context of these feats, Zito was a veritable punching bag as a Giant.
He posted a 4.62 ERA despite the comforts that come with pitching in the National League and at Oracle Park. And out of all pitchers who logged at least 1,000 innings from ’07 to ’13, only Livan Hernandez accounted for fewer wins above replacement.
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Elaine Thompson/Associated Press
Date: December 20, 2007
The Deal: Four years, $48 million
If his rookie season is any indication, Yusei Kikuchi will soon be the Seattle Mariners’ worst free-agent signee since 2000. His 0.5 WAR was the lowest of any pitcher who made 32 starts in 2019.
But until Kikuchi does indeed sink lower, Carlos Silva stands alone in his infamy.
After breaking in as a reliever for the Philadelphia Phillies in 2002, Silva went to the Minnesota Twins and established himself as a solid innings-eater with a 4.42 ERA and an average of 193 innings per year from 2004 to 2007. His reward was a lucrative multiyear deal from the Mariners.
As with most things the Mariners have tried this century, the Silva deal didn’t go well. He made only 36 appearances and logged a 6.81 ERA in 2008 and 2009. The Mariners then traded him for Milton Bradley, who was both bad and clashed with the manager in two seasons with Seattle.
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Jeff Roberson/Associated Press
Date: November 21, 2016
The Deal: Four years, $30.5 million
It was tempting to side with Dexter Fowler’s five-year, $82.5 million contract, but it hasn’t yet gone completely bad for the St. Louis Cardinals.
Fowler had an awful year in 2018, to be sure. But before it came a strong season in the face of injuries in 2017, and after it came a respectable return to form in 2019. So the jury’s out.
Besides, the last three seasons have only further cemented what was apparent as soon as the Cardinals signed Brett Cecil in 2016: It was a mistake.
Though Cecil had been an All-Star for the Toronto Blue Jays in 2013, for the most part he functioned best as a left-handed specialist. He thus faced an uphill climb in justifying his contract in the first place, and it’s only been steepened by carpal tunnel syndrome and the new three-batter-minimum rule.
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Chris O’Meara/Associated Press
Date: January 5, 2009
The Deal: Two years, $16 million
The biggest free-agent contract the Tampa Bay Rays have ever given out was for just $30 million over two years. That was in 2018 with Charlie Morton, who was a Cy Young Award contender in 2019.
In lieu of Morton, James Loney’s three-year, $21 million deal from 2014 and Pat Burrell’s two-year, $16 million contract from 2009 are the only options HERE. And while Loney wasn’t good during the life of his pact, he at least surpassed Burrell.
Before he signed with the Rays, Burrell had averaged an .890 OPS and 31 homers per season with the Philadelphia Phillies from 2005 to 2008. But after he mustered only a .672 OPS and 16 homers in 146 games in Tampa Bay, the Rays designated him for assignment early in 2010.
That worked out fine for Burrell, who caught on with the San Francisco Giants and helped propel them to a World Series title.
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Matt Slocum/Associated Press
Date: December 4, 2006
The Deal: Three years, $33.8 million
Whenever the Texas Rangers sign a big free agent, they tend to get their money’s worth.
Alex Rodriguez crushed it in the first three years of his 10-year, $252 million contract before he was traded to the New York Yankees in 2004. Adrian Beltre became a Rangers icon after signing for $80 million over five years in 2011. Shin-Soo Choo’s seven-year, $130 million pact hasn’t been a steal, but nor has it been a dud.
This put us in a position for a deep cut: Remember when Vicente Padilla was a Ranger?
After arriving from the Philadelphia Phillies via trade in December 2005, he went on to make an impression with a 4.50 ERA over 200 innings in 2006. But upon his re-signing as a free agent that winter, a 5.10 ERA over his next 70 appearances paved the way to his release in August 2009.
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Tony Dejak/Associated Press
Date: November 18, 2016
The Deal: Three years, $33 million
The biggest open-market deal the Toronto Blue Jays have ever done was their five-year, $82 million pact with Russell Martin in 2014. That worked out, as he caught for playoff squads in 2015 and 2016.
As part of an effort to keep the good times rolling, the Blue Jays signed Kendrys Morales in November 2016. On paper, he was meant to fill Encarnacion’s shoes as the club’s primary designated hitter.
That would have been a tall order for any hitter, much less a guy in his mid-30s who was coming off a .795 OPS in 2016.
Though Morales didn’t fall completely apart in Toronto, the 49 homers he clubbed in 2017 and 2018 came with just a .760 OPS. The Blue Jays went no further with the experiment, shipping him to the Oakland A’s ahead of last season.
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Mark Tenally/Associated Press
Date: February 24, 2017
The Deal: Two years, $21 million
The Washington Nationals’ recent track record in free agency is about as good as it gets.
Not one of their nine-figure agreements with Jayson Werth, Max Scherzer and Patrick Corbin backfired. They’ve also scored on smaller deals, including ones with Daniel Murphy and Rafael Soriano.
Therefore, our only option is to snipe at a piece of low-hanging fruit. And Matt Wieters is it.
Though he was coming off an All-Star campaign with the Baltimore Orioles when the Nats signed him in 2017, his best offensive and defensive days were clearly over. So it went for him in Washington, where he was little more than a warm body the Nationals could put behind the plate on an everyday basis.
Stats courtesy of Baseball Reference.