The Worst Trades in Baseball History: 26 Infamous, Head-Scratching Deals

Last Updated: February 7th, 2024 by Jake Cain

Over the course of baseball history there have been some epic blunders when it comes to trades.

Of course, hindsight is always 20-20, but when you look at some of these deals you have to wonder what some of the teams were thinking.

Thanks to our Facebook comments for your input into making our list of the worst trades in baseball history possible.

Let’s dive in:

Babe Ruth From The Boston Red Sox To The New York Yankees

In 1920, one of the most infamous trades in baseball history was completed when Babe Ruth was sold by the Boston Red Sox to the New York Yankees. The Red Sox owner, Harry Frazee, sold Ruth to the Yankees for $100,000, also securing a loan against Fenway Park, which has led to various speculations about the true motivations behind the sale.

At the time, Ruth was already an established pitcher and was emerging as an elite power hitter, making his sale seem shortsighted in hindsight. His departure signified the beginning of the “Curse of the Bambino,” a title for the Red Sox’s subsequent 86-year championship drought, while the Yankees, on the other hand, went on to win four World Series titles with Ruth.

This transaction ultimately shifted the balance of power in the Major Leagues, as Babe Ruth became a baseball legend and cultural icon, profoundly altering the sports landscape in America. Ruth’s powerful hitting helped to redefine baseball as a game where home runs were a crucial and exciting component. The sale price and terms were relatively modest, especially considering Ruth’s future impact on the game, branding this trade as one severely lopsided and pivotal to baseball’s history.

Frank Robinson From The Reds To The Orioles

On December 9, 1965, a trade that is famously considered one of baseball’s most lopsided deals occurred when the Cincinnati Reds sent Frank Robinson to the Baltimore Orioles. The Reds received a package that included pitcher Milt Pappas, reliever Jack Baldschun, and outfield prospect Dick Simpson. Robinson, at age 30, was thought to be past his prime by the Reds but went on to prove otherwise with the Orioles.

Frank Robinson’s Impact with the Orioles:

• 1966 Triple Crown: He won the batting title with a .316 average, 49 home runs, and 122 RBIs.
• MVP Awards: Earned the American League MVP in 1966 and helped guide the Orioles to a World Series victory.

The Trade Fallout:

• Orioles Dynasty: Robinson’s arrival contributed significantly to the Orioles’ dominance, including four World Series appearances in six years

This trade is highlighted as a cautionary tale regarding the assessment of veteran players and their potential contributions to team success.

Randy Johnson From The Expos To The Mariners

In 1989, a towering left-handed pitcher named Randy Johnson was traded from the Montreal Expos to the Seattle Mariners in what is now considered one of the most uneven trades in baseball history. At that time, Johnson showed promise but struggled with control, an issue that the Expos may have viewed as a significant impediment to his success. In exchange, the Expos received pitchers Mark Langston and Mike Campbell, both of whom failed to have a lasting impact with the Canadian team.

Johnson’s trajectory, however, sharply ascended following his move to Seattle. He developed into one of the most dominant pitchers in the game, harnessing his control and leveraging his 6 ft 10 in frame to produce an intimidating presence on the mound. His achievements with the Mariners included a Cy Young Award in 1995, a no-hitter, and multiple All-Star appearances, heavily contributing to the Mariners’ success during the 1990s.

The trade eventually positioned Johnson as a key figure in the Mariners’ franchise history and a hinge point for the Expos, who later became the Washington Nationals. Johnson’s subsequent performances, including perfecting his devastating slider, made the ill-fated decision by the Expos glaringly apparent. The Expos’ short-term gain with Langston, who left the team after the 1989 season, stood in stark contrast to Johnson’s long and illustrious career.

Nolan Ryan From The Mets To The Angels

On December 10, 1971, a trade that would become infamously lopsided occurred when the New York Mets sent Nolan Ryan to the California Angels. The trade was meant to bolster the Mets’ infield with the acquisition of Jim Fregosi, who had prior success as an All-Star shortstop.

However, Fregosi’s performance did not meet expectations, failing to improve the Mets’ fortunes. In contrast, Nolan Ryan blossomed into a dominant pitcher with the Angels, suggesting the Mets had underestimated his potential. His overpowering fastball and no-hitters contributed to his legend, as he consistently racked up strikeouts, even chasing a 400-strikeout season.

Ryan’s tenure with the Angels turned him into a Hall of Fame legend, while Fregosi’s brief time with the Mets was unspectacular. The mismatch in value between the two players led to the trade’s notoriety as one-sided. Considering Ryan’s impact and longevity in the league, the trade remains a cautionary tale about evaluating player potential.

Ryne Sandberg To The Chicago Cubs From The Phillies

In one of baseball’s most lopsided trades, the Philadelphia Phillies sent Ryne Sandberg and Larry Bowa to the Chicago Cubs in 1982. The Phillies received shortstop Ivan De Jesus in return, a move that largely favored the Cubs in the long run. At the time, Sandberg was just a promising minor leaguer, regarded as a secondary piece to the veteran Bowa.

Bowa’s inclusion in the trade helped the Cubs acquire the young infielder whose potential was not yet fully appreciated by the Phillies. Sandberg’s legacy with the Chicago Cubs starkly contrasts with De Jesus’ relatively modest impact with the Phillies. Sandberg would blossom into a 10-time All-Star and a nine-time Gold Glove Award winner commended for his defensive brilliance at second base.

His prolific career earned him a spot in the Baseball Hall of Fame, solidifying the trade as one of the most one-sided transactions. The Cubs enjoyed 15 years of Sandberg’s hall-of-fame caliber play, while De Jesus’s tenure with the Phillies was less impactful. The trade is frequently cited as a cautionary tale of trading away young talent too soon.

Lou Brock From The Cubs To The Cardinals

In 1964, the Chicago Cubs traded Lou Brock to the St. Louis Cardinals in a move that would become infamous as one of the most lopsided trades in baseball history. The Cubs received pitcher Ernie Broglio, who was thought to be a top-tier player but, unfortunately, did not perform to expectations. In contrast, Brock’s career soared with the Cardinals, propelling them to win the World Series that very year.

Brock’s impact on the Cardinals was immediate and profound. He transformed the team’s offense with his exceptional base-stealing and hitting skills. Over his career, he amassed a total of 938 stolen bases, a record that stood until 1991, and earned a reputation as one of the greatest base stealers in baseball history.

The trade’s lopsided nature is highlighted by the accolades and milestones Brock achieved with the Cardinals. He was inducted into the National Baseball Hall of Fame in 1985 on his first ballot, solidifying his status as a baseball legend. Conversely, Broglio’s subsequent struggles with injuries led to a swift decline in his performance and value.

John Smoltz From Detroit To Atlanta

On August 12, 1987, the Detroit Tigers made a trade that would be etched in baseball history as one of its most lopsided. They sent minor league pitcher John Smoltz to the Atlanta Braves in exchange for veteran pitcher Doyle Alexander. Detroit, focused on winning immediately, saw Alexander as the final piece in their push for the postseason.

The immediate impact was tangible; Alexander excelled for the Tigers, posting a 9-0 record with a 1.53 ERA, helping Detroit win the American League East division. However, the long-term consequences of this trade proved to be far more significant for the Braves. Smoltz emerged as a cornerstone of the Atlanta pitching staff, developing into an eight-time All-Star and 1996 Cy Young Award winner.

Smoltz’s career achievements include 213 wins and 154 saves, showcasing his unique versatility as both a starter and a closer. His critical role in the Braves’ dominance throughout the 1990s and early 2000s highlights the trade’s imbalance. In contrast to Alexander’s brief, albeit effective stint with Detroit, Smoltz’s lengthy and storied career with Atlanta rendered the trade a clear victory for the Braves.

Ozzie Smith From Padres To Cardinals

In 1981, the San Diego Padres traded Ozzie Smith, a promising young shortstop, to the St. Louis Cardinals. The trade included six players, with Smith and Steve Mura going to the Cardinals and Garry Templeton heading to the Padres. The crux of the trade was a swap of shortstops between the teams.

While Templeton was an established talent with the Cardinals, it was Smith’s defensive prowess that would shine and leave an indelible mark on baseball history. Smith’s fielding capabilities were transformative; he won 13 consecutive Gold Glove Awards and was selected to 15 All-Star teams. This trade is often deemed lopsided due to Smith’s impact on the game and his eventual Hall of Fame induction.

The Cardinals flourished with Smith, winning the World Series in 1982 and capturing National League pennants in 1985 and 1987. Smith became known as “The Wizard” for his spectacular defense, ultimately making the trade one of the worst for the Padres as they failed to achieve similar success with Templeton.

Miguel Cabrera From Marlins To Tigers

In one of the most lopsided trades in baseball history, the Florida Marlins sent Miguel Cabrera and pitcher Dontrelle Willis to the Detroit Tigers in December 2007. The Marlins, in exchange, received six players, including Cameron Maybin and Andrew Miller, who, despite their potential, never reached the expectations set upon them by the Florida franchise. Cabrera, on the other hand, flourished in Detroit, becoming an integral part of the team’s success.

• Date: December 4, 2007
• To Tigers: Miguel Cabrera, Dontrelle Willis
• To Marlins: Cameron Maybin, Andrew Miller, Mike Rabelo, Dallas Trahern, Eulogio De La Cruz, Burke Badenhop

While Willis struggled with the Tigers, Cabrera’s impact was immediate and profound; he sharpened the team’s competitiveness and became one of the generation’s greatest hitters. With the Tigers, Cabrera earned several accolades, including two American League Most Valuable Player awards and a Triple Crown in 2012, accomplishments that highlighted the trade’s imbalance. The Marlins’ return never matched Cabrera’s contributions, marking the trade as a definitive win for Detroit and a glaring loss for the Marlins.

Glen Davis To The Baltimore Orioles For Steve Finley, Pete Harnisch, And Curt Schilling

In January 1991, the Baltimore Orioles acquired first baseman Glen Davis from the Houston Astros in exchange for outfielder Steve Finley, pitcher Pete Harnisch, and pitcher Curt Schilling. The trade is infamous for its significant imbalance. Davis, who was expected to be a powerful presence in the lineup, struggled with injuries and failed to make a substantial impact during his tenure with the Orioles.

Steve Finley, Pete Harnisch, and Curt Schilling went on to have successful careers after the trade. Finley won five Gold Glove awards and was a two-time All-Star, Harnisch became a reliable starter, and Schilling achieved legendary status, especially for his postseason performances including the “Bloody Sock” game in 2004. The Orioles’ decision to part with these three players, particularly Schilling, who played pivotal roles in multiple World Series championships, is regarded as a major misstep.

The trade serves as a cautionary tale about the risks of trading potential for perceived immediate need. The Orioles sacrificed depth and future star power, a move that set the franchise back for several years. As for the Astros, acquiring Finley, Harnisch, and Schilling greatly benefited their team in the long run.

Pedro Martinez To The Montreal Expos For Delino Deshields

In one of baseball’s most lopsided trades, the Los Angeles Dodgers sent pitcher Pedro Martinez to the Montreal Expos in exchange for second baseman Delino DeShields in November 1993. At the time, the Dodgers considered Martinez to be a promising but expendable arm, mainly due to his slight build, and sought to fill a gap at second base with the acquisition of Delino DeShields, who was a first-round draft pick and had solid seasons behind him.

However, the trade quickly proved to be ill-fated for Los Angeles. Martinez blossomed into one of the most dominant pitchers of his era, earning the 1997 Cy Young Award during his tenure with the Expos. On the other hand, DeShields never reached the expected performance levels with the Dodgers, and his time with the team did not leave the impact Los Angeles had hoped for.

This trade stands out in baseball history as a cautionary tale of trading away young pitching talent prematurely. Pedro Martinez’s Hall of Fame career was just taking off, while Delino DeShields’s production declined after the move, creating a wide disparity in the value each player brought to their respective teams after the trade.

Mark McGwire From Oakland To St. Louis

In July 1997, the Oakland Athletics traded Mark McGwire to the St. Louis Cardinals, a move that remains one of baseball’s most notable trades. McGwire was already an established slugger with Oakland, tallying impressive home run totals, including a then-record 49 in his rookie year. The trade is monumental in baseball history, not only for the impact McGwire made but also for the asymmetry in the value Oakland received in return.

The Athletics acquired pitchers T.J. Mathews, Eric Ludwick, and Blake Stein in exchange for McGwire. In contrast to McGwire’s sustained success, none of these players would have a significant impact on the Athletics’ fortunes. McGwire’s subsequent performances with the Cardinals intensified discussions about the imbalance of the trade; he broke the single-season home run record with 70 home runs in 1998, affirming the trade as particularly one-sided.

McGwire’s enduring legacy with the Cardinals includes not just his 1998 home run record but also his influence on attendance and fan engagement. Oakland’s decision to trade McGwire is often scrutinized for its lack of long-term strategic benefit, exemplifying a trade where immediate needs overshadowed a more lucrative future outcome.

Joe Morgan From Houston To Cincinnati

In one of baseball’s most one-sided trades, Joe Morgan was sent from the Houston Astros to the Cincinnati Reds. The trade occurred in November 1971 and is often cited for its significant impact on both teams’ futures. Along with Morgan, Houston traded Ed Armbrister, Jack Billingham, Cesar Geronimo, and Denis Menke to Cincinnati for Tommy Helms, Lee May, and Jimmy Stewart.

Morgan blossomed in Cincinnati, becoming a key member of the famed Big Red Machine and contributing to consecutive World Series championships in 1975 and 1976. He earned two MVP awards during his time with the Reds and solidified his status as one of the game’s greatest second basemen. Morgan’s profound impact on the Reds’ success starkly contrasted with the Astros’ performance post-trade, which marked this transaction as particularly lopsided.

The trade’s outcome heavily favored Cincinnati, turning the Reds into a powerhouse and leaving Houston with modest gains. Morgan’s Hall of Fame career spanned 22 seasons, touching five teams, but his most impactful years were undoubtedly with the Reds.

George Foster From The Giants To The Reds For Vern Geishert And Frank Duffy

In 1971, the San Francisco Giants traded George Foster, an emerging power-hitter, to the Cincinnati Reds. This exchange involved Foster for two lesser-known players: pitcher Vern Geishert, who never pitched in the majors again, and infielder Frank Duffy, whose career did not rise to prominence.

George Foster developed into a prolific slugger for the Reds, bolstering their lineup as part of the formidable “Big Red Machine.” This nickname referred to the Reds’ dominant teams in the 1970s. Foster’s contribution was significant, clouting homers and amassing RBI’s, which culminated in him winning the National League’s Most Valuable Player award in 1977.

The Giants’ yield from the trade, in contrast, appeared minimal with Duffy playing only 21 games for them before moving on. Geishert’s professional career faded swiftly, highlighting the trade’s lopsided nature. Foster’s impression in baseball history, featuring two World Series championships with the Reds, firmly places this trade among the most uneven player exchanges in baseball lore.

Fred McGriff From San Diego To Atlanta

In July 1993, the San Diego Padres traded first baseman Fred McGriff to the Atlanta Braves, a move that would mark one of the most impactful trades in baseball history. McGriff, a prodigious power hitter, was having a strong season with the Padres when the Braves sought to bolster their lineup for a playoff push. The Braves sent three players — outfielder Melvin Nieves and pitchers Vince Moore and Donnie Elliott — to San Diego in exchange for McGriff’s services.

The Trade:

• From San Diego: Fred McGriff.
• To Atlanta: Melvin Nieves, Vince Moore, Donnie Elliott.

Upon McGriff’s arrival, the Braves saw immediate results. McGriff ignited a struggling Braves offense, leading to a division-winning surge that featured 55 wins in their remaining 67 games. None of the players San Diego received made significant long-term impacts, leading many to deem this an exceptionally one-sided trade.

The trade contributed to the Braves’ dominance in the 1990s and solidified McGriff’s reputation as a key mid-season acquisition. McGriff would go on to help Atlanta reach the World Series in 1995, where they captured the championship. San Diego’s failure to capitalize on the deal further cements the trade as a lopsided transaction in baseball trade history.

Jeff Bagwell From Boston To Houston

On August 30, 1990, the Boston Red Sox made a decision that would be scrutinized for years to come. They traded Jeff Bagwell, a promising 22-year-old, to the Houston Astros for Larry Andersen, a 37-year-old relief pitcher. This trade is widely considered one of the most lopsided deals in the history of baseball.

Bagwell was drafted by the Red Sox in the 4th round of the 1989 MLB June Amateur Draft. Boston’s hope was that Bagwell, a University of Hartford product, would solidify their minor league system. However, Boston sought immediate bullpen help for their playoff push, which culminated in the acquisition of Andersen.

The impact of this trade was felt almost immediately. Andersen pitched in just 15 games for the Red Sox before leaving as a free agent, while Bagwell developed into a cornerstone for Houston. He won the Rookie of the Year in 1991 and the Most Valuable Player Award in 1994, becoming one of the most prolific hitters of his era.

Yordan Alvarez To Houston For Josh Fields

In one of baseball’s most lopsided trades, the Houston Astros acquired Yordan Álvarez from the Los Angeles Dodgers in exchange for pitcher Josh Fields on August 1, 2016. Álvarez, then a 19-year-old Cuban outfielder, was relatively unknown, but demonstrates significant potential at the plate. Fields, a relief pitcher, had fluctuating success with the Astros and was aiming to strengthen the Dodgers’ bullpen.

The Impact:

• Astros: Gained a powerful hitter in Álvarez, who debuted in 2019 and quickly became one of MLB’s most feared sluggers.
• Dodgers: Fields contributed to the bullpen but never matched the impact Álvarez would have for Houston.

The Outcome:

• Álvarez: Emerged as a key player, helping lead the Astros to multiple playoff appearances and earning the title of American League Rookie of the Year in his debut season.
• Fields: Played in Los Angeles until 2018 with a mixed record, later spending time in the minor leagues before becoming a free agent.

This trade highlights the unpredictable nature of player development and the potential for immense gain or loss with each transaction. The deal made with the Astros signing Álvarez to a significant contract serves as a testament to his value for the team. Fields, though a serviceable reliever, did not leave a lasting impact commensurate with Álvarez’s contributions to the Astros.

Heathcliff Slocumb To Seattle For Jason Varitek And Derek Lowe

In 1997, the Seattle Mariners acquired relief pitcher Heathcliff Slocumb from the Boston Red Sox. Slocumb’s performance prior to the trade was lackluster, recording an ERA close to 5. At the time, prospects Derek Lowe and Jason Varitek, who were sent to Boston, appeared as relatively unproven talents.

Lowe and Varitek’s subsequent careers contrasted sharply with Slocumb’s trajectory. Lowe became a pivotal pitcher for Boston, notable for contributing to the Red Sox’s 2004 World Series victory. Varitek became the Red Sox captain, celebrated for his leadership and defensive prowess as a catcher over a 15-year career.

This trade is frequently highlighted as one of baseball’s most unbalanced trades, largely due to the long-term impact Lowe and Varitek had for the Red Sox. Their value extended well beyond Slocumb’s short stint with Seattle, which ended after only one and a half seasons. The trade dramatically exemplified the risk of trading future potential for immediate needs.

Keith Hernandez For Neil Allen

On June 15, 1983, the New York Mets acquired first baseman Keith Hernandez from the St. Louis Cardinals, in exchange for pitchers Neil Allen and Rick Ownbey. At the time of the trade, Hernandez was already an established star, having co-won the 1979 National League MVP and garnered multiple Gold Glove Awards. Allen was a relief pitcher with a respectable record but lacked the standout achievements of Hernandez.

The trade is often cited as one of the most uneven in baseball history. Hernandez went on to play a key role in the Mets’ World Championship in 1986, bolstering the team’s defense and leadership in the clubhouse. In contrast, Allen’s tenure with the Cardinals was not particularly impactful, and he was eventually traded again in 1985.

Factors that contributed to the lopsided nature of the trade included Hernandez’s consistent performance at first base and ability at the plate. Allen, while a solid pitcher, did not perform at the same level or have the same influence on the Cardinals. Additionally, Hernandez’s tenure with the Mets extended well beyond Allen’s time with the Cardinals, solidifying the perceived inequality of the trade.

Tom Seaver For Pat Zachary, Doug Flynn, Steve Henderson, And Dan Norman

On June 15, 1977, the New York Mets orchestrated one of the most controversial trades in baseball history, sending Tom Seaver, a future Hall of Fame pitcher, to the Cincinnati Reds. In return, the Mets received pitcher Pat Zachry, infielder Doug Flynn, and outfielders Steve Henderson and Dan Norman. Labeled as the “Midnight Massacre”, this trade is often cited as a low point for the Mets franchise.

The deal was met with immediate and widespread criticism from both fans and sports commentators. Seaver was an iconic figure, known as “The Franchise” for his instrumental role in the Mets’ 1969 World Series victory. His departure left a lasting void in the Mets’ roster and fanbase.

The players received by the Mets failed to fill the gap left by Seaver. While Zachry had a respectable career, none of the acquired players reached Seaver’s level of impact. Seaver, on the other hand, continued his legacy of excellence, even pitching a no-hitter for the Reds on June 16, 1978, reinforcing the lopsided nature of the exchange.

Fernando Tatis Jr. for James Shields

In June 2016, the San Diego Padres and Chicago White Sox completed a trade that sent a young Fernando Tatis Jr. to the Padres in exchange for veteran pitcher James Shields. At the time, Shields was an established starter, while Tatis Jr. was an unproven prospect.

Shields had accumulated a respectable career Wins Above Replacement (WAR) but struggled significantly following the trade, delivering minimal impact to the White Sox’s rotation. On the other hand, Tatis Jr. rapidly went from being an overlooked minor leaguer to a baseball superstar.

Tatis Jr.’s electric performance with the Padres not only made this trade appear uneven in hindsight but also placed it among the most notably lopsided trades in baseball’s modern era.

Jose Bautista From The Pirates to Blue Jays

In August 2008, the Pittsburgh Pirates traded Jose Bautista to the Toronto Blue Jays for a player to be named later, who would turn out to be catcher Robinzon Diaz. At the time of the trade, Bautista was a utility player with unremarkable statistics, notching a batting average of just .242 during his tenure with the Pirates, detailed on Baseball-Reference.com.

The trade is regarded as one-sided due to Bautista’s dramatic transformation with the Blue Jays, where he became a six-time All-Star and three-time Silver Slugger winner. Bautista’s surge in productivity included leading the American League in home runs for two consecutive years (2010, 2011). His transformation into “Joey Bats,” one of the most feared hitters in baseball, underscored the trade’s imbalance in hindsight.

Rick Wise For Steve Carlton

In 1972, the Philadelphia Phillies and St. Louis Cardinals finalized a trade that is often regarded as one of the most lopsided deals in baseball history. The Phillies sent pitcher Rick Wise, a solid player with a no-hitter under his belt, to the Cardinals in exchange for left-handed pitcher Steve Carlton. Wise was a two-time All-Star, but Carlton’s future impact on the game would reveal the imbalance of this trade.

Steve Carlton went on to become one of the greatest pitchers in baseball, winning four Cy Young Awards and striking over 4,000 batters during his illustrious career. By contrast, Rick Wise continued to be a dependable pitcher, but never reached the heights that Carlton achieved. The trade is highlighted by Carlton’s immediate impact, where he won 27 games for a Phillies team that only won 59 games that season.

The deal is often cited when discussing the influence one player can have on a team’s fortune. Carlton’s tenure with the Phillies included numerous playoff appearances and a World Series championship in 1980. The trade not only shifted the trajectory of both franchises but also placed Carlton on a path to the Hall of Fame, reinforcing its status as a pivotal moment in baseball trading history.

Orlando Cepeda For Ray Sadecki

In May 1966, a trade that would go down as one of the most one-sided swaps in baseball history occurred. The San Francisco Giants traded Orlando Cepeda, known for his powerful hitting, to the St. Louis Cardinals in exchange for pitcher Ray Sadecki. This trade is often compared to other notorious trades of the era due to its uneven outcome.

Orlando Cepeda was a formidable first baseman and a key offensive player. At the time of the trade, Cepeda had already shown his prowess with a stellar 1961 MVP season and was well-loved by Giants fans. His subsequent performance for the Cardinals, including a .325 average and 111 RBIs in 1967, helped propel St. Louis to a World Series Championship.

On the other side, Ray Sadecki, a left-handed pitcher, had a successful 20-win season in 1964. However, his performance did not sustain after the trade, especially relative to Cepeda’s achievements post-trade. Sadecki pitched for the Giants with moderate results, and his inconsistency made the trade seem increasingly imbalanced as seasons passed.

The trade is a classic example of a win-now move, given the Cardinals’ immediate requirement for a powerful first baseman. It illustrates the risks teams take in trading established hitters for pitchers who might not adapt well to new environments. The Giants’ decision to trade Cepeda for Sadecki is a focal point in discussions about risk management in player transactions.

Nolan Arenado From The Rockies To Cardinals

The trade of Nolan Arenado from the Colorado Rockies to the St. Louis Cardinals in February 2021 was viewed by many as imbalanced. Arenado, a five-time All-Star and eight-time Gold Glove winner, was one of the most coveted third basemen in the league. The Cardinals acquired a player in his prime, significantly bolstering their infield and enhancing their competitive standing.

Despite the Rockies receiving a number of prospects and players in return, none matched Arenado’s proven track record. The Rockies also agreed to send a sizable amount of cash to the Cardinals, which further skewed perceptions of the trade’s fairness. This financial aspect, paired with Arenado’s exceptional talent, contributed to the sentiment that the Rockies did not receive adequate value.

Harvey Kuenn For Rocky Colavito

In a move that shocked Cleveland Indians fans, the team traded power hitter Rocky Colavito to the Detroit Tigers in exchange for batting champion Harvey Kuenn on April 17, 1960. This transaction is often cited in discussions on Cleveland sports history and seen as one of baseball’s most imbalanced trades. At the time of the trade, Colavito was coming off a season where he tied for the American League lead in home runs.

Colavito was renowned for his impressive home run-hitting capabilities, exemplified by his 1959 campaign with 42 home runs. In contrast, despite Kuenn’s strong batting average and title as the 1959 American League batting champion, his skill set did not fill the power void left by Colavito’s departure. The trade is notable for its impact on both teams’ performance and the notable decline in attendance at Indians games following the trade.

The Indians’ decision to part ways with Colavito was met with a negative reaction from the fan base; it became more contentious as Colavito remained productive, leading the American League in RBIs in 1965 with the Cleveland Indians. Conversely, Kuenn’s tenure with Cleveland was short-lived; he was traded away to the San Francisco Giants the following year. The trade is still prominently featured in discussions about poor baseball management decisions, particularly because it seemingly ignored the long-term strategic needs of the Indians.