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The 30 worst trades in MLB history

MLB Managers Have a Diversity Problem

The defending champion Kansas City Royals built their core through the draft and trading, as two key contributors to their World Series run – Lorenzo Cain and Alcides Escobar – were acquired in a trade with the Brewers. Last year's award winners were also a great example of how important trades can be to building a team, since both the NL CY Young Winner and AL MVP were acquired in a deal.

SEE ALSO: Home run king Barry Bonds hired as Marlins hitting coach

A boneheaded move by a GM can ruin a team's reputation. Before the Cubs acquired Jake Arrieta, they were known to make a lot of poor moves. Also, the Red Sox valuing $100,000 over Babe Ruth is what led the team to be cursed for 86 years. However, a traded player isn't the most important part of a team's core. Drafting and developing good prospects to build a team's identity then trading for an established player is usually a surefire way to success. The Cubs' core mainly consists of young talent that made impressive strides last season. Because most of their players have yet to reach their prime and are already playing at a high level, that is why people are expecting the Cubs to remain contenders for many years to come.

In this list of the worst MLB trades ever, it's hard to imagine the GM on the losing side of the deal didn't have the best intentions in mind. Even the Babe Ruth trade, $100,000 is just under $1.2 million today – the rumor is that they used the money to finance the production of No, No, Nanette. But as they say, hindsight is always 20-20. Nevertheless, the end result wound up being nothing short of hilarious – or if you're that team's fan, cringe-worthy. With that in mind, let's get to the list.

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30 worst trades in MLB history
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30 worst trades in MLB history

28: Noah Syndergaard to the Mets

The trade: The Mets received Travis d’Arnaud, John Buck, Noah Syndergaard, and Wuilmer Becerra.

The Blue Jays received R.A. Dickey, Josh Thole, and Mike Nickeas.

At the time, this was a very good trade for Toronto. Dickey had just come off of a Cy Young winning season, and was one of the hottest names on the market. Behind J.P. Arencibia, Josh Thole looked to be a player who could provide depth at the catcher position. Then the 2013 season started, and Dickey finished his first season with the Jays with a 14-13 record and an ERA of 4.21. It’s always risky to give away talented prospects for a more experienced player, and at 39, Dickey was entering the journeyman phase of his career.

While he has excelled in 2015 being taken out of the ace role, Syndergaard (or Thor as fans affectionately call him) has been, dare I say, electric for the Mets. He finished the season with a 9-7 record and a 3.24 ERA, pitching in the World Series in his first ever season in the MLB. d’Arnaud, the other key acquisition for the Mets, has also put up impressive stats for the Mets, with a .245 average and 26 home runs in his major league career. In 2015, d’Arnaud made an appearance in the World Series while Josh Thole spent a good part of the season warming the Blue Jays’ bench.

(Photo by Mike Stobe/Getty Images)

27: Vernon Wells to the Angels

The trade: The Angels received Vernon Wells.

Toronto received Mike Napoli and Juan Rivera.

Having hit 223 home runs over the 11 seasons he spent with the Blue Jays, Vernon Wells was by no means a bad player, but after signing him to a 7-year, $126-million contract back in 2006, the Blue Jays were desperate to unload him to another team. The Angels’ owner Arte Moreno was a more than willing bidder, telling his GM that he would be fired if he didn’t acquire Wells within 24 hours.

Wells’ first season with the Angels went poorly, as he finished the season with a .218 batting average, the lowest batting average out of anyone that season with at least 512 plate appearances. He hit 25 home runs, which amounted to $720,000 per home run for Angels ownership.

Even though the Blue Jays ridded themselves of Vernon Wells’ contract, they didn’t do themselves any favours with the pieces they got in return. After acquiring Mike Napoli, they dealt him to the Rangers four days later in exchange for relief pitcher Frank Francisco. In Juan Rivera’s half-season spent with the Blue Jays, he hit 6 home runs and had a batting average of .243. Nevertheless, it was the Angels who found themselves on the losing end of this deal.

(Rick Madonik/Toronto Star via Getty Images)

26: Aramis Ramirez to the Cubs

The trade: Pittsburgh received Bobby Hill, Mike Bruback and Jose Hernandez.

The Cubs received Aramis Ramirez and Kenny Lofton.

The Pirates received an underwhelming package for Aramis Ramirez who they had drafted back in 1998 and showed lots of promise. Jose Hernandez was released at the end of the 2003 season, Bobby Hill had a good 2004 season and not much else, and Mike Bruback never made it to the majors.

In exchange, Aramis Ramirez spent 9 illustrious seasons with the Chicago Cubs. He had a career .294 batting average with the team to go along with 239 home runs and 806 RBI. In the 2003 postseason, Ramirez was the first Cubs player in history to hit a playoff grand slam off of Dontrelle Willis in Game 4 of the NLCS. Even though Kenny Lofton turned out to be a rental for the Cubs, he did his part for the team, collecting a .327 batting average in 68 games played.

From 2003 to 2011, when Ramirez played for the Cubs, Chicago had 3 postseason appearances to Pittsburgh’s zero. Ramirez went back to Pittsburgh in the twilight of his career, hitting 6 home runs in 57 games and a batting average of .243. He would announce his retirement at the end of the season.

(Photo by Doug Pensinger/Getty Images)

22: Josh Donaldson to the Blue Jays

The trade: Blue Jays receive Josh Donaldson.

Oakland receives Brett Lawrie, Kendall Graveman, Franklin Barreto, Sean Nolin.

If not for Moneyball, Billy Beane would probably be out of a job because of this trade. It’s not as if Donaldson became an overnight sensation in Toronto. He was already a highly regarded player, but his 2015 season with Toronto was a breakout year for the AL MVP winner when he, Bautista, and Encarnacion formed the most feared trio in all of baseball.

Donaldson also became the first player to win the MVP right after being traded since 1984 when Willie Hernandez got traded to the Phillies. Donaldson set career highs in home runs (44), RBIs (131), and runs scored (142). He was so good that even Angels fans chanted MVP when he stepped up to bat.

Brett Lawrie’s season, meanwhile, was characterized by at-bats such as this. Lawrie’s time with the Jays was defined by his short temper and extensive injury history, both of which carried over to the Athletics.

The Jays did give up three prospects in Graveman, Barreto, and Sean Nolin which can come back to haunt a team. The Athletics’ only hope of winning this deal is if they can develop these three prospects into budding stars, but as long as Donaldson is still in the prime of his career, the Jays came away big winners in this trade.

(Photo by Rob Carr/Getty Images)

21: Jose Bautista to the Blue Jays

The trade: Toronto receives Jose Bautista

The Pirates receive Robinson Diaz

Josh Donaldson wasn’t the only player who became a star after being traded to Toronto. Prior to arriving in Toronto, Bautista never found a home playing for four different teams. He spent five seasons in Pittsburgh where he never hit more than 16 home runs. Nobody in the Pirates organization could’ve ever imagined Bautista would become the player that he is today.

Robinson Diaz spent two seasons with the Pirates after being traded – the only two seasons he would spend in the major leagues. He hit .295 with 18 RBIs in 31 career games with Pittsburgh before he got optioned back to Triple-A in 2009.

Listing Bautista’s accomplishments would be pure sadism, but I’m going to do it anyway. He’s been named to six consecutive All-Star Games from 2010 to 2015, a 2-time home run leader (in 2010 and 2011 when he hit 54 and 43 home runs respectively) and a 3-time Silver Slugger winner. In his first postseason appearance in 2015, Bautista led his team with 4 home runs, including one in Game 5 against the Rangers that will spawn many oral histories and a 30-for-30 documentary sometime in the future.

(Rick Madonik/Toronto Star via Getty Images)

20: Max Scherzer to the Tigers

The trade: Arizona received Ian Kennedy and Edwin Jackson from the Tigers

Detroit received Max Scherzer and Daniel Schlereth from the Diamondbacks, and Austin Jackson and Phil Coke from the Yankees

New York Yankees received Curtis Granderson from the Tigers

It was only a matter of time before a three-team trade ended up on here. The Yankees were winners, the Tigers were winners and losers at the same time, and the Diamondbacks were big losers. On the one hand, the Tigers were able to flip Ian Kennedy and Edwin Jackson for a Cy Young winner in Max Scherzer. But they also gave up Curtis Granderson and in turn received Austin Jackson and Phil Coke.

However, Granderson was being actively shopped by the Tigers in order to reduce their payroll. Granderson had some great seasons with the Yankees – including 2011 when he was the first player to have 40 home runs, 10 triples, and 25 stolen bases. However, Max Scherzer’s phenomenal contributions to the Tigers (a Cy Young award, the two-time leader in wins in the AL) was more than enough to make up for Granderson’s loss.

Ian Kennedy isn’t a bad pitcher by any means. He won 21 games in 2011 and placed fourth on the Cy Young ballot, but his numbers dipped considerably afterwards before he got shipped out to the Padres. Even though Kennedy served the team well, it’s highly unlikely that Diamondbacks fans are over the fact that they gave up Max Scherzer.

(Photo by Mark Cunningham/MLB Photos via Getty Images)

19: Jake Arrieta to the Cubs

The trade: Chicago Cubs received Jake Arrieta and Pedro Strop

Baltimore received Scott Feldman, Steve Clevenger, and cash

Watching the NL Cy Young presentation must’ve stung for the Baltimore Orioles organization. Lacking a true ace but having a wealth of power hitters, imagine how good the Orioles would be if they had held on to Jake Arrieta. Instead, after witnessing Arrieta’s historic second half of the season for the Cubs, they are left wondering what could’ve been.

Arrieta was with the Orioles for four years. In 2012, he started the season 3-9 with a 6.13 ERA before being sent back down. The Orioles thought they were getting rid of dead weight when they gave him to the Cubs, but instead they gave them a future Cy Young winner.

Scott Feldman spent just one season in Baltimore, pitching to a 5-6 record with a 4.27 ERA before he got shipped off to the Astros. Steve Clevenger, meanwhile, has 2 home runs in 3 seasons with the Orioles. Do I need to bring up Arrieta’s numbers now? Okay, fine.

Arrieta’s second-half of the 2015 season was literally historic. After the All-Star break, he posted an ERA of 0.75 – the lowest mark in MLB history. He gave up a total of nine runs in 15 starts, amassing a 12-1 record. Outside of a complete-game shutout against the Pirates, Arrieta’s post-season numbers left much to be desired. However, that shouldn’t take away from his award-winning season, plus he’s in the prime of his career so he’ll adjust that sooner rather than later.

(Photo by Al Bello/Getty Images)

18: Joe Jackson to the Indians

The trade: Cleveland received Joe Jackson

Philadelphia received Bris Lord

Shoeless Joe Jackson may be most infamous for his involvement in the 1919 Black Sox scandal, but before that, he spent five seasons with the Cleveland Naps (later known as the Cleveland Indians). This was after the Philadelphia Athletics gave up on him and decided to trade him for Bris Lord.

Bris Lord, which sounds like a minister for circumcision, had 13 home runs and a batting average of .256 over his 8-year career. Shoeless Joe bested that batting average in his rookie season. In his first season with Cleveland, Jackson hit .408, a rookie record that still stands. The following season, he batted .395 and led the AL in triples, hits, and total bases. He only had 54 home runs to his name, but that’s not what he was known for.

Jackson became a World Series champion* with the Black Sox, but he provided the Naps with five quality seasons that helped shape his legacy as the baseball legend that he is today. Meanwhile, Connie Mack – the owner of the Philadelphia Athletics – is still convinced to this day that Bris Lord was integral to his team’s success.

(Photo Reproduction by Transcendental Graphics/Getty Images)

17: Lorenzo Cain to the Royals

The trade: Kansas City received Lorenzo Cain, Alcides Escobar, Jeremy Jeffress, and Jake Odorizzi

Milwaukee received Zack Greinke and Yuniesky Betancourt

This proves that it is possible to create a championship core off of a trade. Alcides Escobar enjoyed a breakout year in 2015 and was instrumental in Kansas City’s World Series being named the ALCS MVP. Ultimately, I put Lorenzo Cain’s name in the title because he came in third in AL MVP voting. Odorizzi was included in the package, but he spent most of his time in Kansas City’s AAA affiliate before being shipped out to Tampa Bay for James Shields and Wade Davis.

The Royals won their World Series because of an overall team effort, but these two players stood out, especially in their aggressive base-running. Cain scored the winning run from first on an RBI single in Game 6 against the Blue Jays, and Escobar opened the World Series with an inside-the-park home run.

Sure the Brewers got Zack Greinke – ironically enough, it’s because he didn’t want to play for a rebuilding team – who played well in Milwaukee. However, the rest of the team wasn’t so he was dealt to the Angels for Jean Segura, Ariel Pena, and Johnny Hellweg. Greinke’s selfishness led to him playing for three different teams, and likely a fourth in 2016, while the Royals continue to reap the rewards.

(Photo by Jim McIsaac/Getty Images)

16: Alex Rodriguez to the Yankees

The trade: New York Yankees received Alex Rodriguez

Texas received Alfonso Soriano

A-Rod had just come off of an MVP season in Texas, but the Rangers were looking to move his expensive contract. They figured now was the time to strike while the iron was hot, so they swapped Rodriguez for Alfonso Soriano. In addition, the Rangers had to pay $67 million of Rodriguez’s contract when they dealt him. A-Rod, previously a shortstop, also found a home at third base, which allowed the Yankees to keep Derek Jeter.

Rodriguez wasted no time paying dividends for the Yankees, hitting 36 home runs and 106 RBIs. He would win two more AL MVPs with the Yankees in 2005 and 2007 as well as three more Silver Sluggers, a Hank Aaron Award, and a World Series. And he did all of that while playing by the rules*. His 33 home runs in 2015 proves that he’s still got it.

Alfonso Soriano is a talented player in his own right, but his numbers and awards simply don’t compare to A-Rod’s while he only spent two seasons with the Rangers before being shipped out to the Nationals for Brad Wilkerson, Terrmel Sledge, and Armando Gallarraga.

(Photo by Theo Wargo/WireImage)

15: Frank Robinson to the Orioles

The trade: Baltimore received Frank Robinson

Cincinnati received Milt Pappas, Jack Baldschun, and Dick Simpson

Frank Robinson established himself as an all-time legend with the Cincinnati Reds when he hit 38 home runs in his rookie season. Although the Reds would come close to winning the World Series, losing in 1961 to the Yankees, Robinson never did win a title with Cincinnati. It was only after he got dealt to the Orioles that Robinson became a 2-time World Series champion.

It was a shocking decision for the Reds to ship Robinson over to Baltimore since he was still 30 years old at the time, and still had a lot left in him. Even though Milt Pappas was a good pitcher, the backlash over the deal made it difficult for him to ever get settled in with the Reds, and he was traded after just three seasons. After the trade, Baldschun only recorded one save in his entire career.

Not only did Robinson win two World Series with the Orioles, he led the league in home runs (49), RBIs (122), and batting average (.316) becoming a Triple Crown winner in just his first season in Baltimore. Robinson has been inducted into the Hall of Fame, and his number is retired by both the Reds and the Orioles, but the botched deal – as well as him infamously calling Frank Robinson “an old 30” – forever tarnished Bill DeWitt’s legacy.

(Photo by Focus On Sport/Getty Images)

14: Pedro Martinez to the Red Sox

The trade: Boston received Pedro Martinez

Montreal received Carl Pavano and Tony Armas Jr.

Spoiler alert: this isn’t the only time Pedro Martinez appears on this list. Not long after he became a prized acquisition by the Expos, Pedro Martinez was dealt to the Red Sox in 1997. Martinez was signed to a monster 6-year, $75 million contract which he paid off right away.

In his first season with the Red Sox, he won the Cy Young, and in his second season, he won the pitchers’ Triple Crown by leading the league in ERA (2.07), strikeouts (313), and a 23-4 record. However, among all of his accomplishments, what Red Sox fans will remember most is Martinez leading the team to their first World Series in 86 years, effectively ending the Curse of the Bambino.

What did Montreal receive in return? A rookie in Carl Pavano who pitched to a total record of 24-35 and a 4.83 ERA with the Expos. Tony Armas’ time in Montreal was overshadowed due to various injury concerns, and he filed for free agency in 2006. All told, the Expos never recovered from this deal, as it made the team so bad they had to relocate to Washington.

(Photo credit should read JOHN MOTTERN/AFP/Getty Images)

13: Paul Konerko to the White Sox

The trade: Chicago White Sox received Paul Konerko

Cincinnati received Mike Cameron

Paul Konerko has become synonymous with the White Sox, and they have the Reds to thank for that. Konerko has achieved it all with Chicago. In 2000, they made the playoffs for the first time since 1993 but it was during their 2005 championship run where Konerko came alive.

Over 5 games in the ALCS, Konerko recorded 7 RBIs and was named the ALCS MVP. He then hit a grand slam in Game 2 of the World Series and caught the final out to complete the sweep over the Astros. He would spend the rest of his career in Chicago.

Mike Cameron spent one season in Cincinnati, but for good reason… he was included in a package for Ken Griffey Jr. Cameron’s most iconic moment, hitting four home runs in one game, would come as a member of the Seattle Mariners. Ken Griffey would provide some memorable moments for Cincinnati, but most of his awards came while he was with the Mariners.

Ultimately, what makes the White Sox the winners of this trade is that Konerko will always have something that Ken Griffey never had: a World Series title.

(Photo by Jonathan Daniel/Getty Images)

12: Keith Hernandez to the Mets

The trade: New York Mets received Keith Hernandez

St. Louis received Neil Allen and Rick Ownbey

Keith Hernandez was a star for the Cardinals, as he was instrumental for them in their 1982 World Series victory. However, he and Cardinals management had a falling out and he demanded to be traded. Even though Cardinals manager Whitey Herzog never regretted this deal, everyone else associated with the Cardinals organization was.

Hernandez moved from a World Series winning team to one that had just finished 68-94, but in just his second season, Hernandez turned the Mets’ fortunes around. In 1984, the Mets finished 90-72, 6 and a half games above the Cardinals, while Hernandez came in second in the NL MVP. In addition to being a World Series champion in 1986, Keith Hernandez also dated Elaine Benes and was accused of spitting on a fan.

The players St. Louis got in return did nothing to alleviate fans’ displeasure with the trade. In 1985, Neil Allen had a 1-4 record and a 5.59 ERA. He would later get sold to the Yankees. Rick Ownbey spent most of his time in the minor leagues, and in total started 7 games in a St. Louis uniform.

(Photo by Andrew D. Bernstein/Getty Images)

7: Miguel Cabrera to the Tigers

The trade: Detroit received Miguel Cabrera and Dontrelle Willis

Florida received Dallas Trahern, Cameron Maybin, Andrew Miller, Burke Badenhop, Mike Rabelo, and Frankie De La Cruz

At the time, this didn’t look like such a great trade for the Tigers. It seemed like they were giving up too much for Cabrera and the D-Train who was approaching the tail end of his career. And while Willis’ time in Detroit was plagued by injury, Miguel Cabrera became nothing short of a superstar.

He signed an eight-year, $152 million contract in 2008 which would only be surpassed by his eight-year, $248 million extension in 2014 – a deal so massive that the Tigers had to dip into taxpayers’ money to get it done. His most iconic moments are in 2012 and 2013, when he won his first two MVP awards and achieved a Triple Crown in 2012 – leading the league in batting average (.330), home runs (44), and RBIs (139).

Of the six players that the Tigers sent the Marlins, the only two that panned out were Andrew Miller and Cameron Maybin. With Florida, Miller only appeared in 29 games, went 6-10, and had an ERA of 5.87. He would get dealt to the Red Sox in 2010. Cameron Maybin never spent a full season with the Marlins and he got dealt to the Padres after three seasons.

(Photo by Mark Cunningham/MLB Photos via Getty Images)

5: Curt Schilling to the Astros

The trade: Houston received Curt Schilling, Steve Finley, and Pete Harnish

Baltimore received Glenn Davis

The Orioles shipped out three prospects in search of a first base upgrade over Randy Mulligan. What they got instead was Glenn Davis – no, not “Big Baby” Davis, although their skill set is pretty comparable. Davis had 164 home runs in six seasons prior with the Astros, but a neck injury limited his first season with the Orioles to just 49 games. After three seasons with the Orioles, he retired.

The prospects that Houston received would all become All-Stars later on in their career, although the centerpiece of this deal is obviously Curt Schilling. Schilling currently ranks 15th all-time with 3,116 career strikeouts while he went 11-2 with a 2.23 ERA in the postseason. Even though he only spent one season with the Astros, Orioles fans are left wondering what could’ve been after they parted ways.

Even though Steve Finley’s offensive numbers don’t pop out, he was a steady force for the Astros, while he recorded 13 outfield assists in his first season. Pete Harnish spent just four seasons in Houston, but in that time he compiled a 45-33 record and had an ERA of 3.41.

(Photo by Rick Stewart/Getty Images)

4: Ryne Sandberg to the Cubs

The trade: Chicago Cubs received Ryne Sandberg and Larry Bowa

Philadelphia received Ivan DeJesus

Larry Bowa spent four seasons with the Cubs and brought a veteran presence to the clubhouse. He was meant to fill in for Ivan DeJesus, and he posted a respectable .247 batting average.

Ryne Sandberg, considered a throw-in during the trade, made an immediate impact for the Cubs. He won the NL MVP in 1984 and was a Gold Glove winner for 9 consecutive seasons. He spent 15 seasons in Chicago and had a career .284 batting average to go along with 282 home runs and 2,836 hits. He was inducted into the Hall of Fame in 2005.

As noted before, Sandberg was a throw-in, as this trade was meant to be a swap of shortstops Larry Bowa and Ivan DeJesus. Even though DeJesus had a disastrous season with the Cubs prior to the deal (he hit .194), the Phillies still viewed him as an upgrade over the aging Larry Bowa. He was, but not much of one. He only stuck around for three seasons with the Phillies, while his batting average was a less than stellar .249. The Phillies won the pennant in 1983, but that’s all DeJesus had going for him.

(Photo by Tim DeFrisco/Getty Images)

3: Pedro Martinez to the Expos

The trade: Montreal received Pedro Martinez

Los Angeles Dodgers received Delino DeShields

Delino DeShields Jr. currently plays for the Texas Rangers, but he is likely reminded constantly of the lopsided deal his father was a part of. DeShields filled a need at second base for the Dodgers after Jody Reed left. Once he came to the Dodgers, his batting average slipped from .277 to .241 and he only spent three seasons in LA before he left for free agency.

Despite the fact that Pedro Martinez went 10-5 with a 2.61 ERA for the Dodgers, the team never believed he could become a starter. But once he was dealt to the Expos, he moved into the starting rotation and amassed an 11-5 record with a 3.42 ERA. Martinez would later win the NL Cy Young in 1997 and he finished his career with the Expos with a 17-8 record and a 1.90 ERA. Sure he accomplished more once they sent him to Boston, but it was with the Expos that Pedro Martinez became a superstar.

Wait a second. The Expos made a good trade? Something must be wrong. They must’ve made an equally bad trade to permanently destabilize their franchise.

(Steve Dunn/Allsport)

2: Cliff Lee to the Indians

The trade: Cleveland acquired Cliff Lee, Grady Sizemore, Brandon Phillips, and Lee Stevens

Montreal acquired Bartolo Colon and Tim Drew

And there it is. You know that Bartolo Colon has been in the league for a long time when he was even playing for the Montreal Expos. Lee Stevens and Brandon Phillips were already proven talents, but Grady Sizemore and Cliff Lee were highly regarded prospects. As it turned out, three out of four players would pan out for the Indians, with Cliff Lee becoming one of the best pitchers during his playing time.

Bartolo Colon has played for almost every MLB team in existence – or close to it – and after being acquired at the deadline by the Expos, he and Jorge Nunez were shipped off at the start of 2003 to the Chicago White Sox for Orlando Hernandez, Rocky Biddle, and Jeff Liefer. Tim Drew is famous for being “J.D.’s brother. No, the other one”.

Before he became a perennial All-Star with the Reds, Brandon Phillips developed in the Indians system while Grady Sizemore became a franchise cornerstone for the Indians. He joined the 30-30 club in 2008, had 3 All-Star appearances, and won two Gold Gloves. Cliff Lee also became something of a legend in Cleveland, spending 8 seasons with the team and winning the Cy Young in 2008 after a 22-3 record.

(Photo by Andy Lyons/Getty Images)

1: Babe Ruth to the Yankees

The trade: New York Yankees received Babe Ruth

Boston received $100,000

Because there really was no other choice for number 1. This deal was so bad, so illogical, that there is a curse named after it. After the Red Sox inexplicably sold the best player in baseball to their archrivals for $100,000 in return, they fell under the Curse of the Bambino and couldn’t win another World Series for 86 years. Before the deal, the Red Sox had won five World Series titles, while the Yankees didn’t become perennial winners until after they acquired Babe Ruth. Pretty funny how that works out.

The Red Sox had won five out of fifteen World Series, and Babe Ruth won three of them. Once he moved to the Yankees, he won four World Series titles – the first four in franchise history. 95 years later, the Red Sox still have yet to win four more World Series titles. He was the AL MVP in 1923 and led the AL in home runs 10 times while with the Yankees.

So why did the Red Sox sell the greatest to ever play baseball for $100,000? Nobody knows for sure, although the most popular theory is that the money was used to finance the Broadway production of No, No, Nanette. However, the show’s first performance didn’t come until five years after the Ruth sale and I’m sure it flopped just as badly as the Red Sox after the deal.

Anyway, it’s been fun torturing fanbases revisiting these lopsided trades just as we get set for another crazy offseason. But the MLB has been around for over a century, and as such there have been plenty of bad trades to go around. Narrowing it down to 30 was a difficult task and some had to be left out. But of course, that’s what the comments section is for – if you disagree with a ranking, or you thought a deal should’ve made the list but didn’t, feel free to leave it in the comments below.​

(Photo by Iconic Archive/Getty Images)

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