Ranking MLB's Biggest Blockbuster Trade Busts Since 2000

Zachary D. Rymer@zachrymerMLB Lead WriterJanuary 23, 2022

Ranking MLB's Biggest Blockbuster Trade Busts Since 2000

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    The Giancarlo Stanton trade makes the cut—but only barely.
    The Giancarlo Stanton trade makes the cut—but only barely.Associated Press

    Per the usual definition, a "bad" Major League Baseball trade involves one team making out like gangbusters while the other one ends up with a whole lot of nothing.

    But what if we were to redefine a "bad" trade as one in which neither party got what it wanted?

    Allow us to illustrate by recounting the 10 biggest blockbuster trade busts of the 21st century. These are deals in which a buyer was banking on at least one established star, with the seller placing its hopes in prospects and other building-block types. But in the end, it was all for naught for everyone.

    Let's start with some honorable mentions and then count down the top 10 based on just how badly they backfired. 

Honorable Mentions

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    Jesus Montero
    Jesus MonteroAssociated Press

    Aug. 11, 2008: The Adam Dunn Trade

    The Deal: Arizona Diamondbacks get OF Adam Dunn (-0.4 rWAR); Cincinnati Reds get RHP Micah Owings (-0.9), INF/OF Wilkin Castillo (-0.1) and RHP Dallas Buck (0)

    Dunn did hit eight home runs in 44 games for the Diamondbacks, but they still missed out on a second straight postseason. The trade was otherwise a case of the Reds trying to get something for Dunn before free agency called his number that winter, but none of the three prospects they got back panned out.


    July 31, 2010: The Lance Berkman Trade

    The Deal: New York Yankees get 1B/DH Lance Berkman (-0.3); Houston Astros get RHP Mark Melancon (1.0) and OF/INF Jimmy Paredes (-1.8)

    Acquired to help bolster the Yankees offense for the stretch run, Berkman managed just a .707 OPS down the stretch of 2010. Melancon looks like a major prize for the Astros in retrospect, but it was after he left Houston that he came into his own as a star closer.


    Jan. 30, 2012: The Michael Pineda-Jesus Montero Trade

    The Deal: New York Yankees get RHP Michael Pineda (6.3) and RHP Vicente Campos (0); Seattle Mariners get C Jesus Montero (-1.0) and RHP Hector Noesi (-1.4)

    This one worked out better for the Yankees but not as well as it could have. Pineda missed all of 2012 and 2013 with a bad shoulder, and he was inconsistent after he returned. In Seattle, Montero went from being seemingly a sure thing to one of the most heartbreaking prospect flops in recent memory.


    July 14, 2016: The Drew Pomeranz Trade

    The Deal: Boston Red Sox get LHP Drew Pomeranz (3.9); San Diego Padres get RHP Anderson Espinoza (0)

    In spite of a respectable 17-win season in 2017, Pomeranz was largely up and down in two-plus seasons with the Red Sox following his All-Star breakout in 2016. Espinoza was an elite pitching prospect at the time, but injuries (including Tommy John surgery) have all but destroyed his professional career.

10. Yu Darvish to the Los Angeles Dodgers

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    Matt Slocum/Associated Press

    Date: July 31, 2017

    The Deal: Los Angeles Dodgers get RHP Yu Darvish (0.6); Texas Rangers get OF Willie Calhoun (-1.4), RHP A.J. Alexy (0.1) and INF Brendon Davis (0)


    What Went Wrong for the Dodgers

    After making the American League All-Star team in July, Darvish went to the Dodgers and stumbled with a 5.34 ERA in his first six starts for the team. But he got hot in time for the playoffs, and initially stayed that way by allowing just two earned runs over 11.1 innings in his first two outings.

    Then it all went sideways in the World Series, wherein Darvish coughed up nine runs and got just 10 outs in Games 3 and 7 against the Astros. The revelation of Houston's sign-stealing scandal did bring him some redemption—but not quite enough to cloud the reality that no other Dodgers pitcher got lit up like he did.


    What Went Wrong for the Rangers

    The Darvish traded netted the Rangers three prospects who all ranked within the Dodgers' top 30 for MLB.com. As he was then sitting on a .931 OPS and 23 home runs through 99 games for Triple-A Oklahoma City, Calhoun was certainly the big prize.

    Alas, Calhoun has had buzzard's luck with injuries and just hasn't translated his minor league success to the majors when he has been healthy. Those issues plus the walls hit by Alexy and Davis are not insignificant reasons the Rangers have struggled to escape mediocrity since 2017.

9. Giancarlo Stanton to the New York Yankees

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    Adam Hunger/Associated Press

    Date: Dec. 11, 2017

    The Deal: New York Yankees get OF Giancarlo Stanton (8.4); Miami Marlins get 2B Starlin Castro (2.8), INF Jose Devers (-0.2) and RHP Jorge Guzman (-0.4)


    What Went Wrong for the Yankees

    In fairness to Stanton, he's been pretty good when he's been able to stay on the field over the last four years. He's posted a 134 OPS+ overall and there have been occasional moments when he's lived up to the MVP credentials he boasted when the Yankees acquired him.

    Trouble is, injuries have sidelined him for 217 days just over the last three seasons. And as good as he's been when healthy, he hasn't been the same guy who averaged a 147 OPS+ and 33 home runs in eight years with Miami. He's 32 years old and the Yankees owe him $161 million through 2027, so none of this bodes well for the team.


    What Went Wrong for the Marlins

    As a salary dump, the Stanton trade was a roaring success for the Marlins. Rather than $295 million, the deal lowered their salary commitments to the slugger to just $30 million. At the time, it was easy to imagine new owners Derek Jeter and Bruce Sherman reinvesting that money down the line.

    Instead, they've been about as reluctant to spend as former owner Jeffrey Loria. And while neither Guzman nor Devers was seen as a blue-chip prospect at the time, any hopes that the Marlins would eventually strike gold on one or both of them have thus far been unrealized.

8. Adrian Gonzalez to the Boston Red Sox

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    Charles Krupa/Associated Press

    Date: Dec. 6, 2010

    The Deal: Boston Red Sox get 1B Adrian Gonzalez (9.9); San Diego Padres get 1B Anthony Rizzo (-0.4), RHP Casey Kelly (-1.2), OF Rey Fuentes (-0.3) and INF/OF Eric Patterson (-0.3)


    What Went Wrong for the Red Sox

    There were reasons aplenty for the Red Sox to dream big on Gonzalez, but none greater than the ideal match between the left-handed slugger's opposite-field power and the Green Monster. So big did they dream, in fact, that they extended Gonzalez for $154 million after making the trade.

    No thanks to shoulder surgery, however, Gonzalez's power was a disappointment as he hit just 42 home runs in 282 games with the Red Sox. The team around him also deteriorated, resulting in the Red Sox choosing the nuclear option when they offloaded him and other stars onto the Dodgers in August 2012.


    What Went Wrong for the Padres

    The Gonzalez trade brought the Padres a veritable bag of prospect riches. As he was generally regarded as a future top-of-the-rotation starter, Kelly was the headliner at the time. Rizzo wasn't quite as blue of a chip, but the power and defensive prowess that he offered at the cold corner gave him star-caliber upside.

    After a solid season in the minors in 2011, Kelly unfortunately ran into injury trouble that resulted in Tommy John surgery in 2013. He hasn't been the same since. Rizzo, meanwhile, ended up going to the Chicago Cubs for Andrew Cashner in what quickly came to look like a "bad" trade in the more traditional sense.

7. Troy Tulowitzki to the Toronto Blue Jays

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    Chris O'Meara/Associated Press

    Date: July 28, 2015

    The Deal: Toronto Blue Jays get SS Troy Tulowitzki (5.0) and RHP LaTroy Hawkins (0.1); Colorado Rockies get SS Jose Reyes (-0.2), RHP Jeff Hoffman (-1.4), RHP Jesus Tinoco (-0.1) and RHP Miguel Castro (-0.4)


    What Went Wrong for the Blue Jays

    Paced by eventual AL MVP Josh Donaldson and fellow sluggers Jose Bautista and Edwin Encarnacion, the Blue Jays already had a terrifying offense before Tulowitzki came aboard. But, hey, when you get a chance to add a perennial .300 hitter with power, you have to take the position that overkill is underrated.

    But as he hit just .239 with five homers down the stretch and was mostly ineffective in October, Tulowitzki ended up being more of a defensive upgrade than an offensive one. His bat also never fully rebounded in 2016 or 2017, and he missed all of 2018 with injuries. His five games with the Yankees in 2019 were his last.


    What Went Wrong for the Rockies

    This was an odd trade for the Rockies. Taking on Reyes made it something like a bad contract swap, as he was cheaper than Tulowitzki but still owed close to $50 million through 2017. But it was worth it to get Hoffman, who went into the following season as one of baseball's premiere pitching prospects.

    Come 2016, the Reyes angle of the trade became a PR disaster once he was suspended (and later released) after he violated MLB's domestic violence policy. Like many pitchers before him, Hoffman failed to solve Coors Field and is now an anonymous swingman with the Cincinnati Reds.

6. Randy Johnson to the New York Yankees

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    GREGORY BULL/Associated Press

    Date: Jan. 11, 2005

    The Deal: New York Yankees get LHP Randy Johnson (7.5); Arizona Diamondbacks get OF Shawn Green (0.2), RHP Javier Vazquez (2.0), LHP Brad Halsey (-0.1); Los Angeles Dodgers get C Dioner Navarro (0.7), RHP Beltran Perez (0.0), RHP Danny Muegge (0) and RHP William Juarez (0)


    What Went Wrong for the Yankees

    On the heels of their shocking collapse against the Red Sox in the 2004 American League Championship Series, the Johnson trade was supposed to be the Yankees striking back. After a down year in 2003, he had just missed collecting his sixth Cy Young Award in '04.

    Yet the Big Unit was also north of 40 going into 2005, and he ultimately looked it as he slipped to a modest 112 ERA+ and his worst strikeout rate since 1990. After an even worse season in 2006, the Yankees gave up and shipped him back to Arizona.


    What Went Wrong for the Diamondbacks

    Though the Diamondbacks didn't technically move Johnson in a three-team trade, the team saw it as such after it flipped Navarro to the Dodgers for Green that same day. The outfielder had been one of the game's top sluggers in the late 1990s and early 2000s, and he was still going strong with a 113 OPS+ and 28 home runs in 2004.

    Yet Green hit just 22 homers amid an 85-loss season in 2005 and declined even further in 2006 before the D-backs gave up and sent him to the New York Mets. For their parts, Vazquez and Halsey each lasted just one mediocre season in the desert. The latter tragically died at just 33 years of age in 2014.


    What Went Wrong for the Dodgers

    The Dodgers surely thought they had acquired their catcher of the future when they got Navarro back for Green. According to Baseball America, he had gone into 2004 as the Yankees' No. 1 prospect and the No. 41 talent in all of baseball.

    It was not to be, as Navarro was merely fine for the Dodgers before they traded him to the Tampa Bay Rays midway through 2006. Of the other three players they got in the initial trade, two never even reached the big leagues.

5. Jose Reyes, Mark Buehrle and Josh Johnson to the Toronto Blue Jays

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    Winslow Townson/Associated Press

    Date: Nov. 19, 2012

    The Deal: Toronto Blue Jays get SS Jose Reyes (6.5), LHP Mark Buehrle (6.9), RHP Josh Johnson (-1.5), C John Buck (1.8) and INF/OF Emilio Bonifacio (-0.6); Miami Marlins get RHP Henderson Alvarez III (5.9), RHP Anthony DeSclafani (-0.4), SS Yunel Escobar (0), SS Adeiny Hechavarria (3.6), OF Jake Marisnick (0), C Jeff Mathis (-0.4) and LHP Justin Nicolino (-0.2)


    What Went Wrong for the Blue Jays

    "Nondescript" was a good word to describe the 2012 Blue Jays, yet they exited the season with a reasonably strong talent base to build on. That's where this trade came in, particularly in that it outfitted them with a new starting shortstop (Reyes) and two new aces (Buehrle and Johnson).

    Johnson, however, made just 16 ineffective starts in 2013 before a second and then a third Tommy John surgery ended his career. Though more effective, neither Reyes nor Buehrle lived up to their track records as stars. By the end of 2015, Reyes was in Denver, and Buehrle was absent from Toronto's postseason roster. 


    What Went Wrong for the Marlins

    This was the trade that famously pissed off Giancarlo Stanton. Reyes and Buehrle had just been signed by the Marlins the previous winter and were supposed to be key players in the team's return to contention. It perhaps should have taken more than one bad season for the Marlins to give up on that vision.

    It might have worked out if the players they got in return had blossomed into stars in their own right. Yet Alvarez is the only one that ever really took steps in that direction, and even his were cut short by shoulder surgery in 2015. The others were various forms of misfires and letdowns.

4. Sonny Gray to the New York Yankees

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    Bill Kostroun/Associated Press

    Date: July 31, 2017

    The Deal: New York Yankees get RHP Sonny Gray (1.3); Oakland Athletics get OF Dustin Fowler (-1.0), SS Jorge Mateo (0) and RHP James Kaprielian (1.3)


    What Went Wrong for the Yankees

    For the first half of 2017, Gray looked a lot like the All-Star and Cy Young Award contender he had been in 2015. Between that and his two remaining years of club control, the Yankees understandably jumped at the chance to add him to a roster that was already brimming with exciting young talent.

    Yet Gray struggled, notably with a home run rate twice as high as the one he had in Oakland. Then came two unspectacular playoff starts and a disastrous 2018 season, prompting the Yankees to trade the righty to Cincinnati. It was an insult to injury when he promptly rediscovered his ace form in 2019.


    What Went Wrong for the Athletics

    As ranked by MLB.com, the A's got three of the Yankees' 12 best prospects when they sent Gray to New York. On the low end of that was Kaprielian, though he would have rated more highly had it not been for the Tommy John surgery he underwent that April.

    Though he acquitted himself well with a 100 ERA+ over 119.1 innings for the A's in 2021, the ace ship has likely sailed on Kaprielian. Meanwhile, Mateo is now a bench player on a bad Baltimore Orioles squad, and Fowler is a free agent with all of 18 big league games to his name since 2019.

3. Vernon Wells to the Los Angeles Angels

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    Brad White/Getty Images

    Date: Jan. 21, 2011

    The Deal: Los Angeles Angels get CF Vernon Wells (-0.1); Toronto Blue Jays get C Mike Napoli (0) and OF Juan Rivera (-0.2)


    What Went Wrong for the Angels

    By the time the Angels acquired him, Wells was several years removed from his prime as one of the best offensive and defensive players in the American League. He had nonetheless turned back the clock in 2010, making the All-Star team and finishing with a 125 OPS+ and 31 home runs.

    Wells at least kept the power coming with 25 homers in 2011, but his other skills eroded. In 2012, his durability did the same as he played in just 77 games. Shortly before the opening of the 2013 season, the Angels sent him to the Yankees for what would prove to be his final season.


    What Went Wrong for the Blue Jays

    The Blue Jays might have been tempted to hold on to Wells after he reestablished his All-Star bona fides in 2010. But it was also their last good chance to get to rid themselves of the $86 million remaining on his contract, so the trade was a success, at least in that regard.

    Where the Jays screwed up was in taking Mike Napoli from the Angels and promptly flipping him to the Texas Rangers for Frank Francisco. The righty reliever didn't do much to speak of in 2011, whereas Napoli enjoyed a spectacular year to the tune of a 173 OPS+ and 30 home runs.

2. Ubaldo Jimenez to Cleveland

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    Charles Rex Arbogast/Associated Press

    Date: July 30, 2011

    The Deal: Cleveland gets RHP Ubaldo Jimenez (2.0); Colorado Rockies get LHP Drew Pomeranz (1.4), RHP Alex White (-0.7), RHP Joe Gardner (0) and 1B Matt McBride (-1.3


    What Went Wrong for Cleveland

    Cleveland arguably should have known better than to go all-in on Jimenez at the 2011 trade deadline. Though he had pitched at an All-Star and Cy Young-caliber level in 2010, his first 21 starts of the following year were marked by a pedestrian 102 ERA+ and diminished velocity.

    It, therefore, wasn't terribly surprising when Cleveland's gamble backfired. Despite a decent season in 2013, Jimenez never recovered his previously electric stuff and ended his run in Cleveland with an 87 ERA+ over 424.2 innings. He last pitched with the Baltimore Orioles in 2017 and retired in 2020.


    What Went Wrong for the Rockies

    Especially in light of how far his stock had fallen by the time they dealt him, it was commendable, even at the time, that the Rockies got what they did for Jimenez. Pomeranz and White were both seen as top-100 prospects, while Gardner ranked among Cleveland's top 10 prospects for Baseball America.

    But for his part, Gardner never even made it to the major leagues. White's 30 appearances for the Rockies returned an ERA north of 6.00. Pomeranz fared better, but barely. He posted a 5.20 ERA over 136.2 innings for the Rockies before he landed in Oakland in Dec. 2013 by way of the Brett Anderson trade.

1. Roberto Alomar to the New York Mets

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    Icon Sportswire/Getty Images

    Date: Dec. 11, 2001

    The Deal: New York Mets get 2B Roberto Alomar (0.4), LHP Mike Bacsik (-0.4), OF/1B Danny Peoples (0); Cleveland gets OF Matt Lawton (3.8), OF Alex Escobar (1.5), RHP Jerrod Riggan (-0.6), 1B Earl Snyder (-0.3), LHP Billy Traber (0.3)


    What Went Wrong for the Mets

    Alomar had many fine seasons during his Hall of Fame career, but perhaps none were finer than his 2001 campaign. He hit .336 with 20 home runs and 30 stolen bases and collected his 10th Gold Glove. No wonder the Mets, who were then a year removed from a trip to the World Series, wanted him.

    They would have been wise to study the aging curve more closely. The 2002 season was to be Alomar's age-34 season, and it begat his downfall, as he hit just .266 and barely salvaged replacement-level production. Following further disappointment in 2003, the Mets sent him packing to the Chicago White Sox.


    What Went Wrong for Cleveland

    Following Manny Ramirez's departure in free agency the previous winter, the Alomar trade was something of a double whammy for Cleveland fans. Yet it wasn't entirely without silver linings. Lawton came with All-Star credentials, and Escobar, Traber and Riggan were legit prospects.

    But despite another All-Star nod in 2004, Lawton never really broke through as a difference-maker in Cleveland. Nor did the prospects it got back, which was especially disheartening in the case of Escobar. He tore his ACL in 2002 and couldn't translate his power and speed to the majors in the chances he got in 2003 and 2004.



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