The 10 worst trades in MLB history that still hurt to this day

The 10 worst trades in MLB history that still hurt to this day

Kenneth Mwenda
updated at April 21, 2023 at 4:25 AM

The worst trades in MLB history may rank among the worst in all sports. Major League Baseball produces more terrible trades than any other professional sports league. It is one of the few sports where athletes can reach their peak performance in their late 20s or early 30s.

The 10 worst trades in MLB history that still hurt to this day
Mark McGwire (R) of the St. Louis Cardinals bats against the Milwaukee Brewers at Busch Stadium on April 8, 1999, in St. Louis, Missouri. Photo: Sporting News
Source: Getty Images

Few things in baseball excite fans more than trades, for whatever reason. Fans enjoy witnessing MLB teams' deals, whether during the summer trade season or the winter Hot Stove. However, these transfers result in some of the most one-sided trades in MLB history.

Top 10 worst trades in MLB history

Some teams lose patience with their young talent and trade them away for an experienced veteran with a successful track record. The aging veteran produces about a season or two of respectable numbers before going into a tailspin as the young talent bursts onto the scene with his new team. Below are the top worst trades in baseball history.

10. Nolan Ryan to California Angels

Worst trades in MLB history
Texas Rangers Nolan Ryan in action, pitching two-hitter vs California Angels at Arlington Stadium, Arlington, on 7th July 1991. Photo: Phil Huber
Source: Getty Images

During his time in New York, Ryan was decent but could have been more exceptional. He had many challenging times, along with his brilliant moments. Unfortunately, the Mets abandoned him too quickly and dealt him to the Angels before the 1972 campaign in exchange for Jim Fregosi.

Fregosi had arguably the worst season and a half of his career while playing for the Mets, hitting just.233 in over 146 games. Naturally, Ryan woke up immediately after leaving the Mets. He made his first of eight All-Star Teams during his first season with the Angels, leading the league in strikeouts on his way to Cooperstown.

9. Fernando Tatis Jr. to the Padres

Worst recent MLB trades
Fernando Tatis Jr. of the San Diego Padres before the Spring Training Game against the Chicago White Sox at Peoria Stadium on March 11, 2023, in Peoria, Arizona. Photo: John E. Moore
Source: Getty Images

James Shields earned the moniker "Big Game James" despite having a 3-6 record in the postseason. The White Sox traded a 17-year-old with superstar potential for Shields because they believed they needed a pitcher with the potential to be clutch to aid in their 2016 postseason push. The White Sox failed to make the postseason in any of the pitcher's three seasons with the team, compiling a disgraceful record of 16-35 with a 5.31 ERA in Chicago.

Regarding Fernando, the then-17-year-old, he has lived up to the hype and has turned into one of MLB's current faces. He led the majors in homers in just his third year, has 40/40 potential and has multiple top-five MVP finishes. This is among the worst recent MLB trades.

8. Pedro Martinez to the Red Sox

10 worst trades in MLB history
Pedro Martinez before throwing out a ceremonial first pitch before a game during the 2018 World Series on October 23, 2018, at Fenway Park in Boston, Massachusetts. Photo: Billie Weiss
Source: Getty Images

In exchange for second baseman Delino Shields, the Los Angeles Dodgers traded Pedro Martinez to the Montreal Expos in 1993. Martinez became one of baseball's top starting pitchers, while Shields spent three unsuccessful seasons with the Dodgers.

In his four seasons with the Expos, Martinez went 55-33, winning the first Cy Young Award (presented to the best pitcher in each league) in 1997. In that year, he had a very respectable ERA of 1.90.

7. John Smoltz to the Braves

Worst trade in sports history
John Smoltz of the Atlanta Braves bats during an MLB game against the Chicago Cubs at Wrigley Field in Chicago, Illinois, during the 1993 season. Photo: Ron Vesely
Source: Getty Images

The Tigers decided that trading young pitching prospect John Smoltz to the Braves in exchange for Doyle Alexander would be a good idea in August 1987. It later turned into one of the worst trades in major league baseball history.

Detroit benefited greatly from Alexander's 9-0 record and 1.53 ERA. However, after the division in 1987, he was never the same and eventually retired in 1989.

6. Miguel Cabrera to the Tigers

The worst trades in MLB history
Miguel Cabrera of the Detroit Tigers during the game against the San Francisco Giants at Comerica Park on April 15, 2023, in Detroit, Michigan. Photo: Mark Cunningham
Source: Getty Images

What do you do with a 24-year-old who has played in four All-Star Games and has a.313 career batting average? If you are the Marlins, you trade away one of MLB's most recognisable players because you are concerned about his potential salary demands.

Miguel Cabrera was subjected to that by the Marlins. In the Motor City, Cabrera won four batting titles, two MVP awards, and a Triple Crown, while the Marlins' comeback was utterly embarrassing.

5. Roger Maris to the Yankees

Worst baseball trades of all time
Roger Maris of the New York Yankees lashes a single during the second game of a twi-night doubleheader on 19th September 1961 in Baltimore. Photo: Bettmann
Source: Getty Images

The Athletics sent Maris to New York in exchange for Hank Bauer, Norm Siebern, and the venerable Don Larsen, who threw the only perfect game in World Series history. The Yankees also acquired Joe DeMaestri and Kent Hadley during the transfer.

No one sensed it would be one of the worst MLB trades of all time. Maris ignited baseball in 1961. Partnered with Mickey Mantle, the "M & M Boys," as they were called, sought after Babe Ruth's honoured single-season home run mark of 60.

Mantle and Maris engaged in a battle until Mantle suffered an injury and had to leave the race early. Maris received the Most Valuable Player award for the American League.

4. Randy Johnson to the Mariners

Worst trades in baseball history
Randy Johnson of the Seattle Mariners during circa 1990 game against the Oakland Athletics at the Oakland-Alameda County Coliseum in Oakland, California. Photo: Focus on Sport
Source: Getty Images

Pitchers Mark Langston and Mike Campbell were acquired by the Seattle Mariners in 1989 from the Montreal Expos in exchange for pitchers Randy Johnson, Gene Harris, and Brian Holman. No one knew Randy Johnson would go on to win 303 games, five CY Young awards, one World Series MVP, and ten All-Star selections if the Expos had kept him.

Before joining the Angels, Langston only pitched in 24 games for the Expos. Campbell never started a game for Montreal as a pitcher. The transfer is still Expos' worst trade ever in MLB.

3. Mark McGwire to the Cardinals

The worst trades in major league baseball history
Mark McGwire of the St. Louis Cardinals bats against the Cincinnati Reds at Busch Stadium on July 14, 1998, in St. Louis, Missouri. Photo: Sporting News
Source: Getty Images

The 1997 trade deadline is a forgettable one for the Oakland Athletics. "Big Mac" was getting a huge contract and had already hit 31 home runs. The A's knew they could not afford to keep him because they were on a tight budget.

But the franchise received absolutely no benefits from letting him go on a small amount. McGwire broke Roger Maris' single-season home run records in his first full season with the Cardinals. His team received enough publicity to make up for his enormous contract.

2. Ozzie Smith to the Cardinals

MLB worst trades ever
Ozzie Smith throws out the ceremonial first pitch prior to the game between the St. Louis Cardinals and the Philadelphia Phillies at Busch Stadium on October 07, 2022. Photo: Stacy Revere
Source: Getty Images

Because of his client's San Diego contract, Smith's agent mockingly placed a help-wanted ad in the local paper with the headline "Padre baseball player wants part-time employment to supplement income." This pulled the worst baseball trades of all time.

The Padres' management was so incensed by this that they agreed to trade Smith to St. Louis. But they let their feelings rule and ended up letting the best player in the deal go. With the Cardinals, Smith would go down as the best defensive player in MLB history. However, the prized return for San Diego was Garry Templeton, who spent a decade with the Padres but only appeared in one All-Star Game.

1. Babe Ruth to the Yankees

Most one sided trades in MLB history
Babe Ruth takes a big swing during a batting practice session before a game in 1921 at the Polo Grounds in New York City. Photo: Transcendental Graphics
Source: Getty Images

Ruth was a standout pitcher and hitter for the Red Sox, contributing to three World Series victories for six seasons. It is largely unknown why Harry Frazee of the Red Sox felt compelled to sell him to the Yankees. We do, however, know that Ruth moved to New York and rose to prominence as one of baseball's greatest players.

The Yankees won the American League pennant seven times and the World Series four times during his 14 seasons with the team. More significantly, Ruth sparked a dynasty that continued for decades after his playing days.

Naturally, only some MLB trades will turn out to be advantageous for both parties. You make enough trades to know that some of them will be poor decisions that will undoubtedly backfire. However, some of the worst trades in MLB history now seem completely absurd, and we are left wondering how the decision-makers could have approved such deals.

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Authors
Kenneth Mwenda photo
Kenneth Mwenda
Kenneth Mwenda is a business and sports writer with over five years of experience. At Sportsbrief, he contributes to writing biographies and listicles.