10 Damaging MLB Trades That Still Sting Years Later

Zachary D. Rymer@zachrymerMLB Lead WriterOctober 20, 2021

10 Damaging MLB Trades That Still Sting Years Later

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    Maybe the White Sox would still be playing in the 2021 postseason if they had Fernando Tatis Jr.
    Maybe the White Sox would still be playing in the 2021 postseason if they had Fernando Tatis Jr.Gregory Bull/Associated Press

    If you're a Major League Baseball fan who's still not over, say, the Boston Red Sox's sale of Babe Ruth or the Detroit Tigers' trade of John Smoltz for Doyle Alexander, it's past time you got over it.

    Because while those deals definitely hurt, they're not as painful right now as bad trades that are still actively haunting teams.

    To this end, there are 10 trades that we want to talk about. These deals are now several years old and yet the book on them is still open. And with each chapter, the story is only getting better for one team and worse for the other team.

    To thread this needle, we disregarded deals such as the Red Sox's trade of Mookie Betts in 2020 and the Miami Marlins' trade of Christian Yelich in 2018. The former only had one year of club control left at the time, while the latter has devolved from MVP-winning superstar to oddly mediocre player over the last two years.

    Otherwise, we'll start with some honorable mentions and proceed in chronological order.

Honorable Mentions

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    Nick Wass/Associated Press

    Dec. 19, 2014: Trea Turner to the Washington Nationals

    The San Diego Padres let Trea Turner get away just a few months after they drafted him. Or sort of, anyway, as he couldn't actually join the Washington Nationals until June 2015 because of rules that MLB subsequently amended.

    In any case, Turner went on to become an All-Star and World Series champion in Washington. But at least the deal netted the Padres Wil Myers, who's been good more often than bad in seven years with the team.


    Dec. 19, 2014: Max Fried to Atlanta

    Speaking of bad Padres trades, it's not a great look that they let Max Fried get away on the exact same day that they cut Turner loose. The left-hander has gradually evolved into a top-of-the-rotation starter the likes of which San Diego badly needed this past season.

    Even still, landing Justin Upton in the trade actually worked out fine for the Padres. He had a good year for them in 2015 and the draft pick they secured when he departed was eventually used on Eric Lauer, who was part of the trade that brought Trent Grisham to town in November 2019.


    Dec. 9, 2015: Freddy Peralta to the Milwaukee Brewers

    Starting pitching was a problem for the Seattle Mariners in 2021. Their guys pitched to a 4.61 ERA to rank in the bottom half of the American League.

    It would have helped to have Freddy Peralta, who was sacrificed six years ago so that the Mariners could have a post-prime version of Adam Lind. At least for now, there's the silver lining that Peralta has only one All-Star season under his belt.


    Dec. 15, 2019: Emmanuel Clase to Cleveland

    As you might recall, the thinking at the time of the Corey Kluber trade was that the Texas Rangers had fleeced Cleveland. A two-time Cy Young Award winner for a reliever and a fourth outfielder? Not bad at all.

    Except, now we know that reliever to be one of the best in baseball. Armed with a triple-digit cutter, all Emmanuel Clase did in 2021 was post a 1.29 ERA with 51 hits allowed in 69.2 innings.

The Astros Have More Than One Reason to Regret the Mike Fiers Trade

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    Colin E. Braley/Associated Press

    Date: July 30, 2015

    The Deal: Houston Astros get RHP Mike Fiers, OF Carlos Gomez and cash; Milwaukee Brewers get LHP Josh Hader, RHP Adrian Houser, OF Brett Phillips and OF Domingo Santana

    As they were vying for a playoff berth and they needed a starter and an outfielder, it made sense at the time for the Houston Astros to pay a steep price for Mike Fiers and Carlos Gomez in 2015.

    The Fiers end of the deal worked out at first. Highlighted by the first of his two no-hitters, the right-hander capped the regular season with a 3.32 ERA over 10 appearances to help the Astros make the playoffs for the first time in a decade.

    That was pretty much that, though, as Fiers struggled and fell out of favor in Houston over the next two seasons. Come 2019, he was telling a story that was, shall we say, pretty damning for the Astros organization.

    If that's the injury here, the insult is what's become of Josh Hader and Adrian Houser in Milwaukee. Hader has thrice been an All-Star in five major league seasons, while Houser is fresh of breaking out with a 3.22 ERA over 142.1 innings.

    If the Astros weren't already missing those two, they should be now with their pitching in shambles in the American League Championship Series.

The Diamondbacks Err Going All-in on Shelby Miller

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    Gene J. Puskar/Associated Press

    Date: December 9, 2015

    The Deal: Arizona Diamondbacks get RHP Shelby Miller and LHP Gabe Speier; Atlanta Braves get CF Ender Inciarte, SS Dansby Swanson and RHP Aaron Blair

    It's easy now to pile on then-Arizona Diamondbacks general manager Dave Stewart for how badly the Shelby Miller trade turned out, but dare we give the guy some credit?

    The Snakes did, after all, win 15 more games on his watch in 2015 than they had in 2014. Stewart had also just done a huge free-agent deal with Zack Greinke, who needed a proper co-ace in the desert.

    Stewart could have done a lot worse than Miller. He was fresh off an All-Star season with Atlanta, and he was only 25 and under club control for three more seasons. Which is to say that the D-backs couldn't have anticipated him turning into an oft-injured, sub-replacement-level wreck.

    The book on Inciarte closed with his release in July, but not before he had been an All-Star and three-time Gold Glover for Atlanta. Dansby Swanson, though, has found stardom as a power-hitting shortstop and is still a year from free agency.

    Because this trade loomed large when Stewart lost his job in October 2016, it's little wonder that he came to regret it. Specifically the Swanson aspect of it, as he admitted in 2017 that he should have "stuck to my gut" and held on to the young shortstop.

The White Sox Just Really Had to Have James Shields

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    Jason Behnken/Associated Press

    Date: June 4, 2016

    The Deal: Chicago White Sox get RHP James Shields; San Diego Padres get SS Fernando Tatis Jr. and RHP Erik Johnson

    From one perspective, the Chicago White Sox were indeed in a position to make a splash when they acquired James Shields from the San Diego Padres five summers ago. They were only 1.5 games out of first place in the American League Central at the time.

    From another perspective, the White Sox should have known better. They were mired in a 6-16 funk when Shields came aboard, which looked like an obvious regression to the mean after three straight losing seasons.

    As a reward for throwing caution to the wind, the White Sox got...well, basically nothing. Shields ultimately ended his time on the South Side with all of 0.1 rWAR to show for it.

    Of course, the White Sox have since rebuilt and turned themselves into one of the top powerhouses in the American League. Yet this is no excuse not to miss Fernando Tatis Jr., who's planted himself firmly among the best young shortstops baseball has ever seen since he arrived in San Diego on Opening Day in 2019.

    At least Shields is a good sport about the deal, telling Andy McCullough of The Athletic in 2020, "I walk around town sometimes, and people thank me for the trade."

Don't Blame Josh Fields for the Dodgers' Josh Fields Trade

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    Matt Slocum/Associated Press

    Date: August 1, 2016

    The Deal: Los Angeles Dodgers get RHP Josh Fields; Houston Astros get DH/OF Yordan Alvarez

    At its roots, the story of one of the worst trades in the history of the Los Angeles Dodgers is one of misunderstanding.

    This is according to McCullough, who reported in the Los Angeles Times in 2019 that then-Dodgers GM Farhan Zaidi mistook which Alvarez from Cuba that then-Astros GM Jeff Luhnow asked about as the two were discussing Josh Fields five years ago. Zaidi was thinking Yadier, while Luhnow meant Yordan.

    While Zaidi was adamant that the former Alvarez wasn't going anywhere—at least not right then and there—he was apparently fine with giving up the latter Alvarez. So a deal was struck, and the initial returns were good for the Dodgers.

    In 22 appearances down the stretch of 2016, Fields pitched to a 2.79 ERA with 22 strikeouts. He also came through with four scoreless appearances in October, and he continued to pitch well with sub-3.00 ERAs in 2017 and 2018.

    Nevertheless, the Dodgers released Fields in March 2019. Later that year, Alvarez was named the American League Rookie of the Year. Between that and the .948 OPS and 61 home runs that he has through 233 career games, the Dodgers have every reason to look back on this trade and cringe.

Francisco Liriano Didn't Exactly Work out for the Astros

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    Eric Christian Smith/Associated Press

    Date: July 31, 2017

    The Deal: Houston Astros get LHP Francisco Liriano; Toronto Blue Jays get OF Teoscar Hernandez and OF Nori Aoki

    The Astros have at least one good reason not to regret trading for Francisco Liriano four years ago: It didn't stop them from winning the World Series.

    Though Liriano only pitched to a 4.40 ERA in 20 appearances for the Astros in the regular season, he was mostly good in five outings in the postseason. To wit, he helped stifle a rally in Game 7 of the World Series by retiring eventual National League Rookie of the Year Cody Bellinger in the fifth inning.

    Even in context of all this, though, Liriano was ultimately just an occasionally useful left-handed specialist in Houston. On balance, a player like that isn't quite on the same level as a guy who's become one of baseball's top sluggers.

    When he arrived in Toronto, Teoscar Hernandez had all of four major league home runs to his name. He now has more than 100 just with the Blue Jays, 32 of which came just this past season.

    As then-GM Jeff Luhnow said while Hernandez was finding his stride in 2018, "Any time a player goes off and has success you feel happy for them, but you wonder what could have happened if they had stayed in your organization."

Dan Straily Isn't the Same Pitcher as the One the Marlins Traded for Him

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    Frank Franklin II/Associated Press

    Date: Jan. 19, 2017

    The Deal: Miami Marlins get RHP Dan Straily; Cincinnati Reds get RHP Luis Castillo, RHP Austin Brice and OF Zeek White

    After missing out on a .500 season by only three wins in 2016, the ensuing winter was certainly a time for the Miami Marlins to make some moves in hopes of contending in 2017.

    Of the ones they did make, their deal for Dan Straily was certainly the biggest. Though not exactly an ace-caliber pitcher, he was well established as a solid innings-eater and was coming off a career-best 3.76 ERA for the Cincinnati Reds in 2016.

    Alas, the right-hander never quite lived up to that in his two seasons with the Marlins.

    He posted a 4.20 ERA in 56 starts across 2018 and 2019, both of which were losing campaigns for the Fish. By the latter, the stellar core the Marlins had upon Straily's arrival—Yelich, Giancarlo Stanton, Marcell Ozuna and J.T. Realmuto—was no more thanks to trades.

    In their defense, the Marlins weren't the only team that traded Luis Castillo before he finally debuted in June 2017. But they're the only team that technically traded him twice, making them doubly guilty of missing out on a pitcher who's become an All-Star and one of baseball's leading strikeout artists.

The Giants Traded the Wrong Guy for Andrew McCutchen

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    Eric Risberg/Associated Press

    Date: January 15, 2018

    The Deal: San Francisco Giants get OF Andrew McCutchen and cash; Pittsburgh Pirates get OF Bryan Reynolds, RHP Kyle Crick and international bonus money

    After making the playoffs for the fourth time in seven years in 2016, the San Francisco Giants plummeted to 98 losses in 2017. Even at the time, there were questions about whether they should rebuild.

    Instead, the Giants opted to stay the course. Acquiring Andrew McCutchen was part of that, as he figured to provide a boost for an offense that finished second-to-last in the National League in runs in 2017.

    Trouble was, this wasn't the same McCutchen who was an All-Star and an MVP for the Pittsburgh Pirates between 2011 and 2015. His production had slipped dramatically in 2016 and 2017, and so it went as he managed a modest .772 OPS in San Francisco.

    With the Giants unsurprisingly out of the race heading into the final month of 2018, there went McCutchen again in a trade to the New York Yankees. Neither of the two prospects the Giants got back have amounted to much.

    Bryan Reynolds, meanwhile, has developed into an All-Star since going from to Pittsburgh in the first McCutchen deal. After watching from afar as he hit .302 with 24 home runs this season, the Giants might have especially been missing him as they scored only 10 runs in the National League Division Series.

The Pirates' Gamble on Chris Archer Was Doomed to Fail, and Did

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    Frank Franklin II/Associated Press

    Date: July 31, 2018

    The Deal: Pittsburgh Pirates get RHP Chris Archer; Tampa Bay Rays get RHP Tyler Glasnow, OF Austin Meadows and RHP Shane Baz

    With most trades, you can't really tell whether they're good or bad until you have the benefit of 20-20 hindsight. Any judgments made in the actual moment of a given trade are really just guesses.

    But with the Chris Archer trade, it was as if everyone except the Pirates knew it was a bad idea.

    He wasn't having a particularly good year when the Pirates traded for him, as he was pitching to a 4.31 ERA for the Rays. There was also the reality that the Pirates were putting too much stock in a recent 11-game winning streak, as they were otherwise just three games over .500 for the season.

    Sure enough, Archer stayed mired in mediocrity down the stretch of 2018 and into 2019 as well, and then missed all of 2020 due to surgery for thoracic outlet syndrome. By then, Neal Huntington, the GM who had executed the trade for him, had lost his job.

    Though Tyler Glasnow is currently recovering from Tommy John surgery, both he and Austin Meadows have realized the potential they had when they were top prospects in the Pirates system. Shane Baz isn't there yet, but he's on his way after pitching in the Olympics and in the playoffs for the Rays in 2021.

The One the Rays Hope Will Become 'The Xavier Edwards Trade'

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    Mary DeCicco/Associated Press

    Date: Dec. 6, 2019

    The Deal: Tampa Bay Rays get OF Hunter Renfroe, IF Xavier Edwards and INF Esteban Quiroz; San Diego Padres get OF Tommy Pham and INF Jake Cronenworth

    After the Rays dealt Tommy Pham to the Padres two winters ago, the most pointed criticism was spoken by their very own Cy Young Award-winning ace, Blake Snell.

    "We gave Pham up for Renfroe and a damn slapd--k prospect?" Snell, who ironically got traded to the Padres a year later, said of the deal during a Twitch stream.

    To be fair, said "slapd--k prospect" is now one of the best in the game. Xavier Edwards checks in at No. 79 in B/R's top 100 following a season in which he hit .302 for Double-A Montgomery. Esteban Quiroz also had a quality year with a .974 OPS, mostly for Triple-A Durham.

    It's all up to Edwards and Quiroz to justify this trade, however, because that ship has already sailed for Hunter Renfroe. He did little of note in 2020 and was swiftly cut loose last November.

    In the meantime, Jake Cronenworth's two seasons with San Diego have yielded an .808 OPS, 25 home runs and an All-Star berth. Missing out on that would hurt bad enough if the Rays were merely a rebuilder right now. It's worse that they're a win-now team that gave away a potentially game-changing weapon.

The One the Cardinals Hope Will Be 'The Matthew Liberatore Trade'

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    Jeff Roberson/Associated Press

    Date: Jan. 9, 2020

    The Deal: St. Louis Cardinals get LHP Matthew Liberatore, C Edgardo Rodriguez and 2020 supplemental second-round pick; Tampa Bay Rays get OF Randy Arozarena, OF Jose Martinez and 2020 supplemental first-round pick

    Even more so than the Rays-Padres trade from the previous slide, the book is far from closed on the deal that brought Matthew Liberatore to the St. Louis Cardinals in January 2020.

    As of yet, the trade hasn't had any benefits for the Cardinals at the major league level. But in spite of his modest 4.04 ERA for Triple-A Memphis in 2021, Liberatore is a well-regarded prospect who ranks at No. 45 overall in our top 100.

    It says a lot, though, that Cardinals president of baseball operations John Mozeliak was apologizing for this trade less than a year after making it. As he said last October, per Derrick Goold of the St. Louis Post-Dispatch, "We will revisit how we rank our own players and make sure that we don't have something like this happen again."

    This is, of course, Randy Arozarena's doing. His first 164 games with the Rays have produced an .838 OPS with 27 home runs and 24 stolen bases, which isn't even counting all the history he's made with both his bat and his legs in the last two postseasons. 

    As set as the Cardinals are in the outfield with Tyler O'Neill, Harrison Bader and Dylan Carlson, even better would be O'Neill, Bader and Arozarena.


    Stats courtesy of Baseball Reference, FanGraphs and Baseball Savant.


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