Building a top-of-the-line MLB roster is no simple task, but there have been quite a few general managers and executives over the years, who have made it look damn near impossible. While it is painful to watch your favorite team make a bad signing—it is even more depressing when they make a horrendous trade.
Let’s take a look at 10 of the worst trades in MLB history!
Babe Ruth Trade
The deal the Red Sox made that sent Babe Ruth to the New York Yankees, their vaunted rival, in exchange for $125,000 always springs to mind when the topic of terrible trades gets brought up. Not only was it a horrible deal in the moment, but it also set in motion a multi-generational curse that tortured Red Sox fans for decades.
Anthony Rizzo Trade
It is unbelievable that San Diego was willing to serve up star talent on a platter to Chicago by sending Anthony Rizzo, along with Zach Cates to the Cubs for Kyung-Min Na and Andrew Cashner.
Cashner was supposed to be the cornerstone of the deal for the Padres, but the flame-throwing pitcher never really panned out at the big-league level. Meanwhile, Rizzo went on to become the heart and soul of the Cubs—and led them to their first World Series title in over 100 years.
Click on ‘Follow Us’ and get notified of the most viral MLB stories via Google! Follow Us
Pedro Martinez Trade
Months after Pedro won the NL Cy Young award, having posted a 17 and eight record and 1.90 ERA, the Montreal Expos dealt him to Boston for Carl Pavano and Tony Armas Jr.
Granted, they made the deal because they thought the Dominican native would walk the following offseason, but that weak of a haul for a pitcher as talented at Pedro, who was just ascending toward his peak is inexcusable.
Jose Bautista Trade
Jose Bautista never even hit more than 16 homers in a season—and was just a .241 hitting during his Pirates career. No shocker that Pittsburgh didn’t think twice about sending him up north for Robinzon Diaz, another forgettable name from that era.
Little did they know the change of scenery—and perhaps some helpful teachings from the Blue Jays’ coaching staff—turned Bautista into one of the best hitters in the American League. He was an All-Star in six of his 10 seasons in Toronto and drilled nearly 300 dingers and knocked in 766 runs. Meanwhile, Diaz never amounted to anything.
Steve Carlton Trade
After earning three trips to the All-Star Game as a member of the St. Louis Cardinals, Steve Carlton felt he deserved some extra dinero in his contract. St. Louis’ front office at the time, however, was hell bent on lowballing him. When they deteriorated into a contract dispute, the team’s owner shipped Carlton out to Philly for Rick Wise.
Wise went on to be an average pitcher for the Cards, which, is nice. But he couldn’t hold a candle to the four Cy Youngs, 241 wins and 3.09 ERA that Carlton notched during his Phillies career.
Luis Gonzalez Trade
The Arizona Diamondbacks have made plenty of questionable decisions over the years, but dealing Karim Garcia for Luis Gonzalez was not one of them.
The 31-year old had a resurgence in the desert, making five All-Star games, batting a hair under .300 and smashing 224 homers.
Oh, and he was pivotal in the D-Backs legendary 2001 World Series run.
Lou Brock Trade
Lou Brock was one of the most electric players in baseball.
Unfortunately for the Cubs, they decided to part ways with him at the ripe age of 25, sending him, along with Jack Spring and Paul Toth, to the Cardinals, a division rival, in exchange for Ernie Broglio, Doug Clemens and Bobby Shantz.
Brock went on to a Hall of Fame career—and even helped the Cards to a World Series during his first year.
Randy Johnson Trade
There are a number of reasons that the Montreal Expos don’t exist anymore—and the decision to deal Randy Johnson, along with Gene Harris and Brian Holman, to the Mariners for Mark Langston and Mike Campbell is a big one of them.
Montreal was trying to fast-track its way to success by bringing in a proven vet in Langston, but he’d go on to pitch just 24 games for the Expos before skipping town.
Mark McGuire Trade
Same story, different decade. The Oakland A’s sold off Mark McGuire at the trade deadline—when he had already pinged 31 homers—because they didn’t want to pay him the following offseason.
To make matters worse, they traded him for spare parts, in the form of three forgettable pitchers: T.J. Matthews, Blake Stein, and Eric Ludwick. Yes, Oakland lost its leverage, but there simply had to be a better deal than that available somewhere.
Jeff Bagwell Trade
To say Boston made a rash decision trading Jeff Bagwell to the Astros for Larry Anderson is the understatement of the century.
They were eager for a reliever to bolster their pen during the 1990 playoff push, but the 37-year-old pitcher would throw just 22 frames for the Sox, meanwhile, Bagwell would go on to have a Hall of Fame career with the Astros.
