Ranked the 10 Worst Trades in MLB History

There have been some genuinely awful trades in MLB history. Some have set teams back for years, while others have had a ripple effect that changed the course of baseball history. Here are the 10 worst trades in MLB history.

1. Red Sox Trade Babe Ruth to the Yankees -15 seasons (1920-34)

The Red Sox is one of the most storied franchises in MLB history, but they made a mistake when they sold Babe Ruth to the Yankees in 1920. The move set the Sox back for years, as they went 15 seasons without winning a World Series. The Yankees, meanwhile, won 26 championships with Ruth on their team. This trade is often cited as the reason for the “Curse of the Bambino.”

2. Cubs Trade Lou Brock to the Cardinals- 16 seasons (1964-79)

The MLB odds are not in the Cub’s favor regarding this trade. On June 15, 1964, the Cubs traded outfielder Lou Brock, pitcher John Buhl, and pitcher Paul Toth to the St. Louis Cardinals for pitchers Ernie Broglio, Doug Clemens, and Bobby Shantz. This has been considered one of the worst trades in MLB history, as Brock went on to have a Hall of Fame career with the Cardinals. In 16 seasons with St. Louis, Brock batted .293/.343/.410 with 2,616 hits, 1,610 runs scored, and 900 stolen bases. He was a six-time All-Star and won two World Series titles with the Cardinals.

Meanwhile, the Cubs got minimal production from the players they acquired in the trade. Broglio only pitched two seasons for the Cubs, compiling a 5.40 ERA in 29 starts. Clemens never played a game for the Cubs and was traded to the Houston Astros before he made his MLB debut.

3. Tigers Trade John Smoltz to the Braves- 21 seasons (1988-99, 2001-09)

The Detroit Tigers have made some bad trades in their history, but none was worse than when they traded John Smoltz to the Atlanta Braves in 1987. Smoltz went on to have a Hall of Fame career, spending 21 seasons in the majors, 13 with an ERA+ of 130 or higher.

He was a vital member of the Braves dynasty of the 1990s, winning the Cy Young Award in 1996 and helping the team win five NL pennants and one World Series title. The Tigers got nothing in return for Smoltz, as the Braves sent them only a player to be named later (who turned out to be minor-league pitcher Pete Smith). It’s one of the most lopsided trades in MLB history and the worst trade in the Tigers’ history.

4. Red Sox Trade Jeff Bagwell to the Astros- 15 seasons (1991-2005)

On June 27, 1991, the Red Sox traded the first baseman, Jeff Bagwell, to the Houston Astros for relief pitcher Larry Andersen. It was one of the worst trades in MLB history, as Bagwell went on to have a Hall of Fame career with the Astros while Andersen only pitched 13 innings for the Red Sox before being traded again. Bagwell was just 23 years old when he was traded, but he had already shown plenty of promise in the minor leagues. In 1990, he hit .333/.408/.601 with 18 home runs and 16 stolen bases for the Double-A New Britain Red Sox. The Astros saw him as a potential star, and they were right.

5. Yankees Trade Fred McGriff to the Blue Jays-19 seasons (1986-2004)

The Fred McGriff trade is often cited as one of the worst trades in MLB history. The Yankees traded McGriff to the Blue Jays for Jesse Barfield and Dale Murphy in 1986. Barfield was a solid player for the Yankees, but he was nowhere near as good as McGriff. Murphy was a bust with the Yankees and was out of baseball by 1989. Meanwhile, McGriff went on to have a Hall of Fame career with the Blue Jays, hitting .293/.374/.516 with 2,490 hits and 493 home runs. He was a five-time All-Star and won two World Series titles with the Blue Jays. The Yankees would surely love to have McGriff back in their line-up today.

6. White Sox Trade Sammy Sosa to the Cubs- 13 seasons (1992-2004)

The White Sox traded Sammy Sosa to the Cubs in what is widely considered one of the worst trades in MLB history. The deal was made before the 1992 season and saw Sosa sent to Chicago along with pitcher Ken Patterson and minor leaguer George Bell for infielder Scott Fletcher, outfielder Luis Salazar, and pitchers Steve Buechele and Drew Henson. Sosa would go on to have a Hall of Fame career with the Cubs, slugging 609 home runs while being named to seven All-Star teams. He was also a vital member of the Cubs team that finally broke the franchise’s prolonged drought and won the World Series in 2016.

7. Mariners Trade Jason Varitek to the Red Sox- 15 seasons (1997-2011)

The Seattle Mariners traded Jason Varitek to the Boston Red Sox on July 31, 1997, in a deal that is often considered one of the worst trades in MLB history. In return, the Mariners received relief pitcher Heathcliff Slocumb, while the Red Sox got a three-time All-Star catcher who would go on to win two World Series titles with the team.

8. Pirates Trade Jose Bautista to the Blue Jays-10 seasons (2008-17)

In 2008, the Pirates traded Jose Bautista to the Blue Jays. Bautista would go on to have a remarkable career with the Blue Jays, becoming one of the best power hitters in baseball. The Pirates, meanwhile, got nothing in return for Bautista and ultimately made one of the worst trades in MLB history.

9. Marlins Trade Christian Yelich to the Brewers- 5 seasons (2018-present)

The Miami Marlins have made a lot of terrible trades in their franchise history, but none is more damaging than when they traded Christian Yelich to the Milwaukee Brewers. Yelich was one of the best young players in baseball and was under team control for five more seasons. The Marlins got very little in return for him, and the trade has set the franchise back years.

The Marlins have been one of the worst teams in baseball since the trade, and they are still trying to recover from it. Yelich has gone on to win an MVP award and be one of the best players in baseball.

10. Padres Trade Anthony Rizzo to the Cubs- 10 seasons (2012-21)

It’s been 10 years since the Padres traded Anthony Rizzo to the Cubs in one of the worst trades in MLB history. The Padres have never been able to replace Rizzo’s production at first base, and the trade is often cited as a critical reason why the team has failed to make the playoffs since 2006. Meanwhile, the Cubs went on to win the World Series in 2016, largely thanks to Rizzo’s contributions. Rizzo is a three-time All-Star and has won two Gold Glove Awards. He’s also been one of baseball’s most consistent power hitters, averaging 28 home runs and 93 RBIs over the past six seasons. The Padres made a number of other poor trades around the same time as the Rizzo deal, but none have been as damaging as this one.

Bottom line

These are some of the worst trades in MLB history. These teams gave up on players who went on to have great careers. In many cases, the teams that traded these players got very little in return. These trades set these franchises back years, and they are still trying to recover from them.