Every MLB Team's Most Regretful Trade Since 2010

Despite not having a salary cap, MLB has surprisingly had a lot of parity over the past decade. While the decade has seen the Giants win three World Series titles in a span of five years, as well as the Red Sox winning a couple of championships, we see teams go up and down every year. Payroll hasn't always equated to a team having success, as somehow the Oakland A's have managed to make the playoffs every few years, while the Tampa Bay Rays continue to develop solid players.

What goes a long way in determining how well a team does is how they manage their assets. Drafting doesn't mean as much as it would in other sports, as baseball talents can be found without going through the draft and when teams need another batter or pitcher, they simply offer up some of their assets to get it. Teams have to know when they can get the highest possible return for their players and when to sell off some of their prospects.

Every team in the majors has at least one trade over the past decade that they would like to have back. The difference between successful franchises and floundering franchises is how quickly they can recover from their mistakes and minimizing the big ones. So now, let's go through all 30 ball clubs and determine which of their trades over the 2010s that they'd like to have back.

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30 Arizona Diamondbacks: Trading Chris Johnson & Justin Upton For Prospects

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 In 2012 the Diamondbacks had just come off an 81-81 season. Their former first overall selection, Justin Upton hit 17 home runs and had 67 runs batted in. Owner Ken Kendricks expressed the motivation for trading Upton: "He's certainly not the Justin Upton that he has been in the past and that we would expect of him,'' Upton would be shipped to the Braves and the following six seasons would earn two Silver Slugger awards and become a 2- time All-Star.

29 Atlanta Braves: Craig Kimbrel & Melvin Upton Jr. For Jordan Paroubeck, Cameron Maybin, Carlos Quentin, Matt Wisler

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It's not unusual for it to take a while for potential prospects to fully develop, but it has been three years since this trade and Jordan Paroubeck has yet to make it to the big leagues, Cameron Maybin played a season in Atlanta, Matt Wisler is 16-23 with the Braves and Carlos Quentin was released by the Braves nine days after the trade. Whereas Melvin Upton Jr. was not a huge loss, Craig Kimbrel currently has 142 saves since the trade and three All-Star appearances.

28 Baltimore Orioles: Jake Arrieta, Pedro Strop & Cash For Steve Clevenger & Scott Feldman

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In 2013 the Baltimore Orioles were in the midst of an 85-77 season, looking to stay in the Wild Card hunt, the Orioles and Cubs made a trade. The Orioles got Scott Feldman who would go 5-6 prior to being granted free agency as well as Steve Clevenger who tallied two home runs. The Cubs got Pedro Strop who is 17-19 since the trade, and Jake Arrieta, who was 20-25 for his career in Baltimore.  Post-trade, Arrieta had two All-Star selections and a Cy Young.

27 Boston Red Sox: Rey Fuentes, Casey Kelly & Anthony Rizzo For Adrian Gonzalez

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In December of 2010, the Boston Red Sox called up the San Diego Padres to deal for Adrian Gonzalez. In his first year with Boston, Gonzalez was an All-Star, a Gold Glove and Silver Slugger winner. Before trading him to the Dodgers, Gonzalez hit .321 with 42 home runs in 282 games. While Fuentes and Kelly were a small price to pay, the minor leaguer in Anthony Rizzo, has currently made 4 All-Star teams and has won a Gold Glove and Silver Slugger.

26 Chicago Cubs: Tyler Colvin & D.J. LeMahieu For Casey Weathers & Ian Stewart

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After just 60 official plate appearances in 2011, the Chicago Cubs traded D.J. LeMathieu and Tyler Colvin to the Colorado Rockies for Casey Weathers and Ian Stewart. Colvin would hit 21 home runs in 162 games with the Rockies, but LeMathieu is the big regret. Maybe it is the air, but, LeMathieu has become a 2-time All-Star and a 3-time Gold Glove winner since the trade. Ian Stewart would step into the batter’s box 202 times for the Cubs, while Casey Weathers never got the call to the big leagues.

25 Chicago White Sox: Chris Sale For Luis Alexander Basabe, Victor Diaz, Michael Kopech & Yoan Moncada

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It is never easy to grade a baseball trade that is just two years old, however, even though the White Sox were going to trade Sale regardless, they should be regretting the return they got. Sale has gone 29-12 with the Red Sox and in 2018 he had a 2.11 ERA. Moncada quickly became a top prospect in the White Sox Organization but has hit just 15 home runs. Kopech has appeared in just 4 games with a 5.02 ERA.

24 Cincinnati Reds: Aroldis Chapman For Eric Jagielo, Caleb Cotham, Rookie Davis & Tony Renda

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On July 25th, 2016 the Cincinnati Reds were looking to replenish their organization with some young talent and they used their best chip to do so. Part of the trade also had to do with Chapman's off-field issues. Since being traded by the Reds, Chapman has earned 58 saves with an 8-4 record and one All-Star appearance. So far the Reds return has netted them two wins, seven losses and six home runs. Time may turn the tides, but as of right now, there has to be some regret.

23 Cleveland Indians: Brandon Moss For Rob Kaminsky

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The Indians may not be crying over the loss of a utility player who has 30 home run potential that can play first base, thanks to Yonder Alonso occupying that particular corner. It is the fact that Brandon Moss has some experience roaming right field, a position the Indians have Melky Cabrera and Tyler Naquin in currently. Since being traded for Rob Kaminsky, Moss has had seasons of 28 and 22 home runs, Kaminsky has a 26-20 record in the minors.

22 Colorado Rockies: Huston Street For Nick Schmidt

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How could trading a pitcher out of Colorado be a regretful decision? Well, it could be when that pitcher goes on to have two more All-Star seasons while having three seasons with an Earned Run Average of under 2.00. Those shiny ERA seasons might not exist, or the 146 saves if he remains in Colorado, but Street’s statistics would be easier to overlook if Nick Schmidt would have had more than one season in the minors with an ERA below 3.30.

21 Detroit Tigers: Yoenis Cespedes For Luis Cessa & Michael Fulmer

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Everybody knows that the Tigers traded Justin Verlander, but the 2015 deal with New York Mets becomes the franchise’s most regretful trade. Luis Cessa would never throw a pitch for the Tigers, while Fulmer has tallied a 24-31 record and a career Earned Run Average of 3.80, thanks to his Rookie of the Year winning season. Despite missing numerous games the last two season, Cespedes has proven to not only be an All-Star but be a Gold Glove and Silver Slugger caliber player when healthy.

20 Houston Astros: Hunter Pence For Jarred Cosart, Jon Singleton, Josh Zeid & Domingo Santana

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Since being traded in 2011, Hunter Pence has hit 121 balls out of the park, while knocking in 500 runs. At the very least, he's made the Astros regret not being able to get more for him. In return, the Astros acquired Jarred Cosart who went 10-8 in one season. Jon Singleton was recently released despite his last appearance being in 2015, Josh Zeid has appeared in 28 games, none since 2014 and Domingo Santana managed 42 plate appearances before being traded along with Josh Hader.

19 Kansas City Royals: Zack Greinke & Yuniesky Betancourt For Lorenzo Cain, Alcides Escobar, Jeremy Jeffress & Jake Odorizzi

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Lorenzo Cain played seven seasons for the Royals with an average of .289 and 120 stolen bases. Alcides Escobar has competed in eight seasons with the Royals obtaining one All-Star selection and a Gold Glove, Jeremy Jeffress managed to go 1-1 with an ERA of over 5.00, and Jake Odorizzi only got into 2 games with the Royals. With all that said, the Royals traded Zack Greinke for that haul in 2010 and he has since tallied up 127 wins, three All-Star selections, and three Gold Gloves.

18 Los Angeles Angels: Ervin Santana & Cash For Brandon Sisk

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Since being traded from the Los Angeles Angels in 2012 to the Kansas City Royals, Ervin Santana has accumulated a 53-45 record accompanied by a 3.64 ERA. Granted, the Angels were able to rid themselves of the $13 million that would have been owed to Santana in the upcoming season, he still had a better ERA than every starter the Angels had in 2013. Sisk was considerably cheaper, and had his best season was with the New Jersey Jackals, where he went 5-1.

17 Los Angeles Dodgers: Rafael Furcal & Cash For Alex Castellanos

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Perhaps trading for Manny Machado will soon replace this 2011 mid-season trade, but until then, the immediate regret they felt by paying the St. Louis Cardinals to take Furcal for Castellanos is at the top. In two years with the Dodgers, Castellanos had 42 plate appearances with a .171 batting average. Since then he has signed on as a free agent four times and was released every time without getting an at-bat. Furcal would get 748 plate appearances and make an All-Star team.

16 Miami Marlins: Giancarlo Stanton For Jose Devers, Jorge Guzman, Starlin Castro

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Despite the Tigers getting a temporary pass on trading Verlander, the Florida Marlins are not afforded that luxury. With the lack of awful trades since 2010 (because most players just leave) the Stanton trade sticks out even more. Stanton’s 38 home runs, 100 runs batted in and .266 average did not win him any All-Star, MVP or Silver Award like the previous year, but Guzman’s 0-9 minor league record in 2017 and Devers one career home run in the minors, is not entirely promising.

15 Milwaukee Brewers: Zack Greinke For Johnny Hellweg, Ariel Pena, And Jean Segura

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After Zack Greinke went 25-9 for the Brewers over two seasons with 49 games started, the Milwaukee Brewers thought it was time to move Greinke to the Los Angeles Angels. While Jean Segura made an All-Star team in Milwaukee, his best seasons have occurred after Milwaukee traded him. Hellweg went 1-4 in seven starts in 2013 while Pena has a career record of 2-1. As for the Brewers, they could have used Greinke in Game 7 of the 2018 NLCS.

14 Minnesota Twins: Aaron Hicks For John Ryan Murphy

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Back in 2015 when the Twins traded Aaron Hicks for catcher John Ryan Murphy, Hicks had a .225 batting average and 20 home runs over 819 at-bats with the Twins. Since the trade, Hicks has a .244 batting average with 50 home runs in 1,108 official at bats. Hicks showed more power and more speed than anybody the Twins had in center field in 2018. Plus, to make it more regretful, John Ryan Murphy played in only 26 games for the Twins before being traded.

13 New York Mets: Carlos Beltran For Zack Wheeler

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 The Mets are probably happy that Zack Wheeler is still playing and managed to go 12-7 with a 3.31 ERA in 2018, but back in 2011 when the Mets traded Carlos Beltran and his $19 million contract, it's possible they could have received more in exchange. Beltran still had three All-Star seasons after the trade and have an average of 500 at-bats, 22 home runs and 74 runs batted in. The Mets wound up recovering from this trade thanks to a stellar pitching staff, but they could've used Beltran's bat in their lineup.

12 New York Yankees: Mark Melancon & Jimmy Paredes For Lance Berkman

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In 2010 the New York Yankees were on their way to make it to the ALCS where they would eventually lose in six games to the Texas Rangers. At the trade deadline, the Yankees added Berkman who would have just three hits in 12 at-bats during the ALCS. Berkman would go on to have an All-Star 2011 season with the Cardinals. Melancon would turn his 9.00 ERA with the Yankees into 182 career saves elsewhere. All in all, the move really didn't help the Yankees at all.

11 Oakland Athletics: Josh Donaldson For Brett Lawrie, Kendall Graveman, Sean Nolin & Franklin Barreto

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When you trade a player that goes on to be the MVP for the team that acquires him, that sure leads to some regret. The Oakland A's had Josh Donaldson but knowing he would soon be due a massive payday, sent him to Toronto for Brett Lawrie. Donaldson was always a solid player for the A's, but they couldn't have foreseen the jump he would take following the move to Toronto. His MVP play allowed the Jays to reach back to back ALCS series, while the A's had to re-tool once again.

10 Philadelphia Phillies: Jim Thome For Daniel Haigwood, Aaron Rowand & Gio Gonzalez

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Since the Phillies re-signed Cliff Lee after trading him in 2009, their most regrettable trade ends up being, trading a future Hall of Famer for a career minor leaguer, 29 home runs and Gio Gonzalez who never played for them. The stats show Thome had a lot left, after being traded Thome had an average of 37 home runs and 102 RBI per 162 games. Thome would end up re-signing with the Phillies in 2012 prior to being traded again.

9 Pittsburgh Pirates: Gerrit Cole For Jason Martin, Michael Feliz, Colin Moran & Joe Musgrove

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Knowing they would not be able to contend in the NL Central, the Pirates traded Gerrit Cole, who just came off a 12-12 season with a 4.26 ERA, stats that would improve to the tune of 15-5 with a 2.88 ERA. Meanwhile, Jason Martin hit 13 home runs in the minors, Michael Feliz had a 5.66 ERA, Colin Moran hit .277 with 11 home runs while Joe Musgrove went 6-9 with a 4.06 ERA. It seems the Pirates are never able to keep players in their prime.

8 San Diego Padres: Zach Cates & Anthony Rizzo For Kyung-Min Na and Andrew Cashner

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In 2011 Anthony Rizzo only managed 153 plate appearances with the Padres, so swapping him for Andrew Cashner who would end up with a 28-43 record with a 3.67 ERA over five years, did not seem too bad. Kyung-Min Na, never made it to the majors once the Padres acquired him, but, in the Padres defense, neither did Zach Cates. The problem, Anthony Rizzo has gone on to be a 3-time All-Star, 2- time Gold Glove and Silver Slugger winner.

7 San Francisco Giants: Luis Castillo & Kendry Flores For Casey McGehee

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The Giants may be in a down period now, but they did win three World Series titles in the 2010s. It is difficult to not regret a trade whenever you give up a couple of young arms for a couple of home runs. McGehee had 138 plate appearances before being released by the Giants, only to sign back with the Marlins two days later in 2015. McGehee's 27 hits and 28 strikeouts will end up being worse once the 24-year-old strikeout per inning Castillo develops into an ace.

6 Seattle Mariners: Cliff Lee & Mark Lowe For Matt Lawson, Blake Beavan, Josh Lueke & Justin Smoak

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After being traded by the Mariners, Cliff Lee still had 45 wins, two All-Star seasons and two top-five Cy Young Award seasons in him. Even if the Mariners are not regretting also adding Mark Lowe, the bounty of players in return added up to 17 wins, 21 losses and 66 home runs. Aside from Lee, Justin Smoak is the only name worth mentioning, and his best years came after the Blue Jays selected him off waivers from the Mariners.

5 St. Louis Cardinals: Kyle Barraclough For Steve Cishek

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The Cardinals are one of the better run organizations in baseball so they don't have a lot of bad moves to speak of. Kyle Barraclough’s 15-12 career record with the Marlins accompanied by a 3.21 ERA is not currently causing anybody in the front office of the St. Louis Cardinals to lose sleep. The potential Barraclough has as a future closer drastically outweighs the production that the Cardinals got from Steve Cishek. In 2015, Cishek pitched 23.1 innings and then was promptly allowed to become a free agent in the offseason.

4 Tampa Bay Rays: David Price For Willy Adames, Drew Smyly & Nick Franklin

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This was a three-way deal between the Rays, Tigers and Mariners at the trade deadline of 2014. Price had already been a 3-time All-Star and a Cy Young award winner, prior to the trade, post-trade he accumulated a 68-28 record, including a sparkling 2-0 record with a 1.98 ERA in the 2018 World Series. In return the Rays acquired Adames who hit .278, Smyly who is 15-15 with a 3.95 ERA and Franklin hit 10 home runs in 338 plate appearances.

3 Texas Rangers: Chris Davis & Tommy Hunter For Koji Uehara

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Chris Davis is set to make $23 million until 2022, a contract that reflects his past stats, and not the ones he's putting up now. Unfortunately for the Texas Rangers, they were stats that were obtained with another team. Davis has hit 241 home runs since the trade, while Uehara pitched 51 innings for the Rangers over two seasons. For good measure, the Rangers threw in Tommy Hunter to grease the wheels. Hunter would go on to go just 21-20, thankfully not adding to the regret.

2 Toronto Blue Jays: Wuilmer Becerra, John Buck, Travis d'Arnaud & Noah Syndergaard For R.A. Dickey, Mike Nickeas & Josh Thole

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In 2015 the Toronto Blue Jays acquired the reigning Cy Young Award winner, granted R.A Dickey would go on to have a 49-52 record with the Blue Jays, Nickeas never got a plate appearance, Thole has accumulated 2 home runs and a, 200 batting average and Beccera has yet to make the jump to the majors. Buck hit 15 home runs the following season, d’Arnaud as 162 runs batted in, while Syndergaard has gone 37-22 with a 2.93 ERA.

1 Washington Nationals: Jonathan Papelbon & Cash For Nick Pivetta

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Jonathan Papelbon had some amazing years in Boston, where he was one of the best closers in the game. Considering the Nationals seemed poised to take over the majors, they felt Papelbon was an essential piece for them being able to close out big games. While the Nationals don't regret trading Nick Pivetta, acquiring Papelbon proved to be a move that messed with the Nats locker room. We all remember the altercation he had in the dugout, not to mention the team missed the playoffs entirely, when Papelbon was supposed to be closing out games.

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