Lopsided Trades in MLB From the Past Decade

Lopsided trades happen in sports all of the time, however, some teams get a little too aggressive and end up overpaying for players. The magnitude of a lopsided trade takes some time to set in. Major League Baseball saw a lot of crazy trades over the past decade, however, these ten trades stand out from the rest.

Lopsided Trade #10: R.A. Dickey to the Blue Jays

As a native-New Yorker, I can attest that Mets fans universally hated this trade initially. R.A. Dickey was coming off a career year in which he won the NL Cy Young Award, going 20-6 with a 2.73 ERA/3.27 FIP (139 ERA+), a 1.053 WHIP, and a league-best 230 strikeouts in a league-leading 233.2 innings (8.9 K/9). It was a great surprise when Mets general manager Sandy Alderson, decided to ship Dickey to Toronto along with catchers Mike Nickeas and Josh Thole. The Mets in return recieved Wuilmer Beccera, John Buck, Noah Syndergaard, and Travis d’Arnaud.

This didn’t become a lopsided trade until 2015. While Dickey was solid across four seasons in Toronto, d’Arnaud and Syndergaard helped the Mets make the World Series. While d’Arnaud has since moved on and Syndergaard has had his fair share of injuries, both have outperformed Dickey, who ended up retiring after the 2017 season. Syndergaard was an All-Star in 2016 and finished eighth in the Cy Young voting that season, demonstrating how good he is when he is healthy. In 2020, d’Arnaud won his first Silver Slugger Award.

Lopsided Trade #9: José Quintana to the Cubs

This lopsided trade could end up even more one-sided, however, it’s only been a few years and this probably isn’t the full return on stats. Jose Quintana was an All-Star on the Southside of Chicago in 2016 but was having a down year in 2017. The Cubs, meanwhile, were desperate for pitching and swung a deal to acquire Quintana in July of that year. In return, the White Sox received Bryant Flete, Matt Rose, Dylan Cease, and Eloy Jiménez.

Quintana was productive down the stretch for the Cubs, going 7-3 with a 3.74 ERA/3.25 FIP and 98 strikeouts in 84.1 innings (10.5 K/9). The Cubs made it to the NLCS, but Quintana’s production lagged soon thereafter, while Jiménez and Cease look to be a big part of the White Sox’ future. Jiménez has already won a Silver Slugger and was a big part of the White Sox making it back to the playoffs in 2020. This trade looks lopsided right now and it may only get better for the White Sox from here.

Lopsided Trade #8: Fernando Tatís Jr. to the Padres

Similar to the Quintana trade, this lopsided trade is only going to get more lopsided as time goes on. In a few years, this trade could become a top-five heist in baseball history. The Padres were looking to trade a struggling James Shields and his bloated contract in the spring of 2016. The White Sox pounced and acquired the right-hander in exchange for Erik Johnson and Fernando Tatís Jr.

Shields was subpar for the White Sox, pitching to a 16-35 record with a 5.31 ERA/5.77 FIP (79 ERA+) and a 1.447 WHIP in 436 innings. Tatís, meanwhile, has become one of the most electrifying players in baseball. Through his first two seasons (143 games), Tatís has hit .301/.374/.582 (156 OPS+) with 39 homers and 27 steals. He finished third in the Rookie of the Year voting in 2019, fourth in MVP voting in 2020, and won his first Silver Slugger. The only reason this lopsided trade ranks as low as it does is because Tatís has only been in the majors for two seasons.

Lopsided Trade #7: Shelby Miller to the D-Backs

This lopsided trade looked bad right from the beginning. The rebuilding Braves were looking to ship All-Star pitcher Shelby Miller to a new team in the winter of 2015. They found a taker in the Diamondbacks, and sent Miller and Gabe Speier to Phoenix in exchange for Aaron Blair, Ender Inciarte, and Dansby Swanson, who was the number one pick in the 2015 draft.

While not everyone the Braves got back in return has performed to expectations, Miller’s time in Arizona was a disaster. He battled injuries and pitched to an alarming 6.35 ERA (71 ERA+) in three seasons. Inciarte and Swanson meanwhile have helped the Braves win three consecutive NL East crowns.

Lopsided Trade #6: Yasmani Grandal to the Dodgers

After becoming General Manager of the Padres in the fall of 2014, A.J Preller was very aggressive that offseason. In December of that year, he splurged to acquire Dodgers star Matt Kemp, giving up Zach Eflin, Joe Wieland, and Yasmani Grandal.

Kemp had a couple of solid seasons offensively in San Diego, but any offensive value was negated by his horrendous defense. Kemp only put up 0.7 rWAR with the Padres, which was far below expectations for a guy getting paid $21 million per season. He was eventually dealt to the Braves in July of 2016.

On the other hand, Grandal became one of the best catchers in baseball during his time in Los Angeles. He was an All-Star in 2015 and overall hit .238/.337/.453 (113 OPS+) with 89 homers. He was fantastic defensively, with 82.5 framing runs and overall compiling an fWAR of 19.8.

Lopsided Trade #5: Chris Archer to the Pirates

The Pirates made a number of bad moves in the 2010s, but this looks like the worst one. In the summer of 2018, the Pirates rattled off 11 consecutive wins before the All-Star Break. They decided to buy at the Trade Deadline, and splurged to acquire Chris Archer from the Rays. In return, the Pirates sent Austin Meadows, Tyler Glasnow, and a player to be named later.

Unfortunately for the Pirates and Archer, the team couldn’t sustain their momentum and missed the playoffs. Archer underperformed in Pittsburgh, pitching to a 4.92 ERA/4.71 FIP (85 ERA+) during his tenure there.

On the other side of the coin, Meadows and Glasnow have developed into legitimate franchise cornerstones. Meadows was an All-Star in 2019 and finished 14th in MVP voting. Glasnow has turned into an ace-type pitcher, averaging 12 strikeouts per nine innings and pitching to a 3.32 ERA/3.40 FIP (129 ERA+). Both of these players helped the Rays reach the ALDS in 2019 and the World Series in 2020. To make matters worse for Pittsburgh, the player to be named later ended up being top-100 prospect Shane Baz.

Lopsided Trade #4: Luis Castillo to the Reds

The Marlins have made a number of awful trades in their history, and there was no shortage of them in the 2010s. The crazy part about them trading Luis Castillo is that they actually traded him twice. In July of 2016, Castillo was sent to San Diego in a package for pitchers Colin Rea and Andrew Cashner. Castillo was then sent back to Miami three days later after Rea was found to have an injury that the Padres failed to disclose before the trade. The Marlins waited a few more months before sending Castillo to the Reds as part of a deal for Dan Straily.

Straily was mediocre in Miami, pitching to a 4.20 ERA/4.79 FIP (93 ERA+) in two seasons with the team. Castillo, however, has turned into the ace of the Reds’ pitching staff. He was an All-Star in 2019 and has pitched to a 3.62 ERA/3.77 FIP (124 ERA+), a 1.168 FIP, and 578 strikeouts in 519.2 innings (10.0 K/9). Castillo is only 27, while Straily hasn’t pitched in the majors since 2019. This is another lopsided trade that may only get worse for the Marlins.

Lopsided Trade #3: Gerrit Cole to the Astros

The only trade that was somehow more lopsided than the Archer trade for the Pirates was this one. Cole had been a solid contributor for five seasons in Pittsburgh, making one All-Star team and compiling a 3.50 ERA/3.27 FIP (112 ERA+). The Pirates were in rebuilding mode and sent Cole to Houston in exchange for Joe Musgrove, Michael Feliz, Jason Martin, and Colin Moran.

While the Pirates haven’t necessarily gotten bad numbers from their side of this trade, Cole became a superstar in Houston. In his two seasons with the Astros, Cole was an All-Star twice, a top-five Cy Young finisher twice, and pitched to a blistering 2.68 ERA/2.67 FIP (164 ERA+), a 0.962 WHIP, and an even more insane 602 strikeouts in 412.2 innings pitched (13.1 K/9). His performance earned himself a record-setting contract following the 2019 season worth $324 million.

Lopsided Trade #2: Christian Yelich to the Brewers

In the 2017-18 offseason, new Marlins owner Derek Jeter decided to trade away all three of his team’s star outfielders. Yelich was the last one to get dealt, as he was sent to Milwaukee in January of 2018. In return, the Marlins received prospects Lewis Brinson, Monte Harrison, Isan Díaz, and Jordan Yamamoto.

The returns on this trade haven’t panned out for the Marlins. Díaz, Harrison, and Brinson have all looked overmatched in the majors, suffering from horrible strikeout problems. Yamamoto was solid in 2019 but was shelled during his brief time in the majors in 2020.

In Milwaukee, Yelich has done nothing but mash baseballs. In his three seasons with the Brew-Crew, he has hit a monstrous .308/.405/.599 (162 OPS+) with 92 homers, 70 doubles, 56 steals, and 14.5 rWAR. He won the NL MVP in 2018, finished second in MVP voting in 2019, made two All-Star Games, won two Silver Sluggers, won two Batting Titles, and led the NL in OPS twice. Maybe the prospects the Marlins received will pan out eventually, but right now, this trade has been very one-sided.

Lopsided Trade #1: Josh Donaldson to the Blue Jays

This move is not only the most lopsided trade of the decade, it’s one of the biggest head-scratchers in history. The A’s had seven All-Stars in 2014, but a collapse in August relegated them to a Wild Card spot. Surprisingly, the team was blown up, and six of the seven All-Stars were gone less than 12 months later. Donaldson was shipped out to Toronto in exchange for Brett Lawrie, Sean Nolin, Franklin Barreto, and Kendall Graveman.

Five years later, none of the players that the A’s acquired are in the organization. None of them were able to perform to expectations, and two of them (Lawrie and Nolin) are no longer in baseball. Donaldson, meanwhile, was a monster in Toronto. He hit a remarkable .281/.383/.548 (148 OPS+) with 116 homers and 19.2 rWAR. Donaldson made two All-Star Games, won AL MVP in 2015, and helped the Blue Jays snap their 23-year playoff drought.

Closing Thoughts on Lopsided Trades

Lopsided trades happened a lot in the 2010s. Some of them didn’t seem that way initially, but as time went on, the results showed that one team definitely got the better part of the deal.

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Main image credit: Embed from Getty Images

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Mathias Altman-Kurosakihttp://overtimeheroics.net
Mathias is a senior journalism major at The College of New Jersey. He has served as the Sports Editor and Opinions Editor for the school's newspaper, The Signal. He joined Overtime Heroics as a writer in June of 2019 and became an editor in December of 2020. Mathias is also a varsity swimmer and is the youngest of five kids.

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