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Top 10 Most Lopsided Trades in MLB History

Baseball
Top 10 Most Lopsided Trades in MLB History

Remember the days when you went to school dreading that awful moment when the school bully took all of your lunch money and left you empty-handed.  Well, that’s basically what happened during these unbalanced trades. In Major League Baseball, general managers usually alternate being the bully and being the loser. Meanwhile, history has proven over and over again that most lopsided trades result from over-hyped prospects and underrated veterans.

These egregious trades can result of the team’s financial limits or can happen for reasons as selfish as an individual player wanting to play in another city. For those elite players that are able to negotiate outrageous contracts or hold a team hostage in favor of their personal needs, the trade deadline is like Christmas Day. For others, it’s judgment day. It’s often just the cost of doing business for working in the big leagues. But it hurts a little bit more when you realize you gave a future Hall of Famer to another team for pocket change.

Consider 21-year old Texas Rangers prospect, Sammy Sosa, being traded to the Chicago White Sox along with Wilson Alvarez and Scott Fletcher for Harold Baines and Fred Manrique. Although Sosa only played with the White Sox for a few seasons, the Rangers missed out huge. They say hindsight is 20/20, but that’s certainly no consolation to the teams that were left empty-handed. Regardless, trade rumors can be as exciting as they are explosive with repercussions that could last for years. Looking back through history, these are top 10 most lopsided trades in Major League Baseball.

10. Jeff Bagwell – Boston Red Sox to Houston Astros (1990)

BAGWELL

In exchange for mediocre reliever, Larry Andersen, the Boston Red Sox sent future All-Star infielder Jeff Bagwell to Houston where he would play out the rest of his very successful 15-year career. Boston was experiencing a surplus of players vying for the same position at the time of the trade that helped influence Bagwell’s departure. Bagwell lost first base to three-time All-Star Mo Vaughn and the Red Sox organization was unsure that he could successfully make the transition to another infield position. With a variety of different factors involved, Boston’s talented prospect went out to Houston where he won NL Rookie of the Year in 1991, appeared in 4 all-star games and won 3 Silver Slugger Awards.

9. Curt Schilling & Co. – Houston Astros to Philadelphia Phillies (1992)

WORLD SERIES 1993

Curt Schilling is no stranger to the trade as the right-handed future Hall of Famer was traded 5 times during his career. While it’s hard to argue which of those five was the worst, Schilling’s move to Philly marked the beginning of a successful trade career. Although, Schilling only spent one season with the Astros before being sent to the Phillies, the loser here is still Houston (and also Baltimore who had trade Schilling to the Astros a year before). The Astros received Jason Grimsley, who had an average reliever for 15 years.

While Schilling had a respectable run in Philadelphia, he was reportedly unhappy with the team’s performance and eventually found himself in Arizona. The move paid off in a big way for Schilling, as he went 22-6 with a 2.98 ERA and helped lead the Diamondbacks to a World Series title alongside fellow ace, Randy Johnson.

8. Cliff Lee & Co. – Montreal Expos to Cleveland Indians (2002)

Cliff Lee

During the 2002 regular season, the Cleveland Indians figured their season was going to be long and disappointing. The Montreal Expos were teetering on the edge of extinction and made a desperate attempt to win. So they traded away ace pitcher Bartolo Colon and a player later to be named as pitcher Tim Drew went to Montreal in exchange for first baseman Lee Stevens and three prospects. Those prospects were pitcher Cliff Lee, outfielder Grady Sizemore and infielder Brandon Phillips. While Bartolo Colon continues to have a successful career, if this crazy one-way deal hadn’t happened maybe there’d still be a professional baseball team in Montreal. All 3 players went on to have terrific careers, with Cliff Lee being considered one of the best pitchers of this generation.

7. Randy Johnson – Montreal Expos to Seattle Mariners (1989)

JOHNSON

The Expos traded away arguably the most dominant left-handed pitcher of all time. Nearing the daunting trade deadline in 1989, Montreal sent pitching ace Randy Johnson to the Seattle Mariners for Mark Langston, one of the better pitchers in Mariners history, and a prospect. After the Expos shipped Johnson out of Montreal, he went on to win 5 Cy Young Awards and a World Series Championship over his career. Langston played a single season in Montreal before moving onto the Angels.

The Mariners ended up moving Johnson, but at least received two capable players in Freddy Garcia and Carols Guillen.

6. Nolan Ryan – New York Mets to California Angels (1971)

Nolan Ryan

Arguably the worst trade in New York Mets history, the Mets dealt pitcher Nolan Ryan to the California Angels for 3B Jim Fregosi. Although this trade was not considered controversial at the time it happened, it was a deal that quickly went downhill for the Mets as Fregosi never had a decent season in New York. Nolan Ryan went on to strike out nearly 6,000 hitters during his incredible 27-year career. Although his only World Series appearance came with the Mets, Ryan was an 8-time All-Star Hall of Fame pitcher that could have changed the unfortunate history of the Amazin’ Mets had he stayed in town.

5. Jason Varitek & Derek Lowe – Seattle Mariners to Boston Red Sox (1997)

LOWE VARITEK

As is the case with most controversial trades, the severity of the repercussions do not reveal themselves immediately. When Boston wanted relief pitcher Heathcliff Slocumb out of the clubhouse and managed to score Jason Varitek and Derek Lowe from the Seattle Mariners in 1997, it seemed to make sense. Fast forward five to ten years and you’d be hard-pressed to find anybody that could validate that transaction anymore. Varitek went on to win 2 World Series titles, a Golden Glove and Silver Slugger Award and was invited to 3 All-Star games during his career in Boston. Derek Lowe had the best portion of his career with Boston and helped them break the curse of the Bambino in 2004. Slocumb had a decent 10-year career as a Major League pitcher but never managed to achieve the success Lowe and Varitek did.

4. Miguel Cabrera – Florida Marlins to Detroit Tigers (2007)

Jerry Lai/USA TODAY Sports Images

Jerry Lai/USA TODAY Sports Images

In one of the most lopsided trade in the history of Major League Baseball, the Florida Marlins dropped the ball. The Tigers sent top prospects outfielder Cameron Maybin, pitcher Andrew Miller, catcher Mike Rabelo and minor league pitchers Eulogio De La Cruz, Dallas Trahern and Burke Badenhop to the Marlins in exchange for pitcher Dontrelle Willis and infielder Miguel Cabrera. Although Willis only played a few tough years with the Tigers before shipping out to Arizona, Cabrera posted 37 HR, 127 RBI, and .292 BA over 160 games during his first season in Detroit.

Clearly, Miggy had no issue transitioning from the aggressive National League to work under veteran Jim Leyland’s traditional American style. He’s now widely regarded as the best player in baseball today.

3. Pedro Martinez – Los Angeles Dodgers to Montreal Expos (1993)

MARTINEZ

Although Pedro Martinez hadn’t really been able to display his full potential during his short stint in Los Angeles, the Dodgers definitely found themselves on the sore end of this lopsided trade a few years later. In exchange for Martinez, the Dodgers received Delino DeShields. Martinez went on to win 3 Cy Young Awards and become one of the greatest pitchers in baseball and DeShields played three mediocre seasons with the Dodgers before being traded to the St. Louis Cardinals.

While Pedro’s trade from the Montreal Expos to the Boston Red Sox was considered by many as a worse trade, the Expos couldn’t afford Martinez at the time and would likely have lost him to free agency either way.

2. Frank Robinson – Cincinnati Reds to Baltimore Orioles (1965)

ROBINSON STRIDES AT PLATE

The Cincinnati Reds received starting pitcher Milt Pappas, relief pitcher Jack Baldschun, and outfielder Dick Simpson in exchange for right fielder, Frank Robinson. Robinson led the league with his .316 BA, 49 HR and 122 RBI and won the Triple Crown title in his first season with the Orioles. Robinson had an incredibly successful career following his arrival in Baltimore including two World Series titles, the second of which came defeating the Cincinnati Reds in 5 games in 1970.

1. Babe Ruth – Boston Red Sox to New York Yankees (1920)

BABE RUTH YANKEES

Many fans blame the Red Sox’s former owner, Harry Frazee, for shipping Babe Ruth to New York following the 1919 season. According to Bleacher Report, Boston pocketed $100,000 to get Ruth out of the city as the pre-franchise Yankees unknowingly welcomed the berth of their legacy. Although the reason for Babe’s abrupt departure is debatable, his absence in Boston marked the beginning of a 86-year World Series draught for the Red Sox. Since Babe cursed Boston, the Yankees have dominated Major League Baseball having won 27 World Series Championships.

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