Baseball’s Biggest Blunders: Breaking Down the 10 Worst Trades in MLB History

Trades are the quickest way for a team to strengthen itself. Mostly the MLB franchises trade when a player no longer suits their needs. Sometimes it’s to get better players in exchange, but there are a rare few times when it just doesn’t make any sense. From the legendary Babe Ruth to a future hall-of-famer like Mookie Betts, no player is safe. But then, neither are the teams – because sometimes things just do not go according to the plan.

That’s exactly what happened with some of the greatest franchises. In a sport whose history stretches back to the 1800s, stories just never run out. So here’s how teams like the Boston Red Sox, the Baltimore Orioles, and others made monumental mistakes that led them to a cursed path. 

Deals which changed the future: Babe Ruth to the Yankees and Randy Johnson to the Mariners

1. Babe Ruth –

The year was 1919, the Boston Red Sox were the undisputed kings of the major leagues. In stark contrast to present-day, the New York Yankees were a meandering team with no World Series appearance. Part of the reason was the presence of Babe Ruth in the Beantown. For six seasons, Ruth had rewritten what a ballplayer could be – with the ball and the bat. 

So it becomes even more absurd when Red Sox’s owner Henry Frazee stuck a $100,000 deal with the Yankees to trade Ruth to them. Suddenly, the superstar of Boston was now entering New York. More importantly, with him was entering the glory of the World Series.

The Yankees won 4 World Series with Ruth and that set off the motion that culminated with them winning 27 Fall Classics – the most in MLB. On the other hand, the “Curse of Bambino” hit the Red Sox, who ended up going on an 86-year World Series drought.

2. Randy Johnson

Not to be outdone, the former Montreal Expos traded Randy Johnson to the Seattle Mariners. They had drafted the pitcher in 1985 but couldn’t figure out a way to use him. So it was natural that they chose to trade him to the Mariners. But what happened next was inexplicable.

Johnson went on to win 5 Cy Young awards, 4 ERA titles, and 10 All-Star selections. To top it all off, the ace won a World Series with the Arizona Diamondbacks and was named MVP of that series. What happened to the Expos?

They never made it to the World Series and moved to Washington – thus becoming the Washington Nationals. The story has just started, MLB is filled with similar blunders.

Fear gone wrong: Marlins ditches Miguel Cabrera and the Rangers lose trust in Sammy Sosa

3. Miguel Cabrera

In 2007, the Florida Marlins decided that at that point looked quite sensible. They trade Miguel Cabrera and Dontrelle Willis to the Detroit Tigers for six top prospects. That seemed like a great bet on the future, but things went wrong. One of those prospects never played in the major league and the rest proved to be ineffectual for the Marlins. On the other hand, Cabrera ended up creating history for the Tigers.

The slugger won four batting titles, became back-to-back MVP, and was a triple crown. All of that led to him creating a future MLB Hall-of-Fame career. One wonders if the Marlins wish they held on to him a little longer. However, this mistake wasn’t as big as what the Rangers made with Sammy Sosa.

4. Sammy Sosa

Sammy Sosa played for just one year in the Texas Rangers. The team decided to trade him after the 1989 season. However, they weren’t the only ones – even the Chicago White Sox traded Sosa to their city-rivals, the Chicago Cubs. One wonders how the White Sox felt during 1998 when Sosa became part of the legendary home-run race that revived the waning popularity of baseball. 

Mariners trade Jason Varitek, the Mets Trade Nolan Ryan, Red Sox trade Mookie Betts, regrets later

5. Jason Varitek

The Seattle Mariners have been on both ends of a blundereous trade. While Randy Johnson’s trade benefited them, just a few years later, they made a big mistake. In 1997, the team needed to improve its bullpen and traded their prospect, Jason Varitek, to the Boston Red Sox. The move that was designed to benefit the M’s ended up becoming the catalyst for ending the Red Sox’s 86-year curse. However, Varitek became the central figure in their 2004 World Series win.

6. Nolan Ryan

In 1965, the New York Mets made a historic draft pick in Nolan Ryan. However, the pitcher struggled with control during his time there. So, in a bid to improve their squad, the team traded Ryan to the California Angels in 1971-72. In a surprising turn of events, Ryan suddenly became an elite pitcher and averaged 21 wins in his first three seasons. The ace ended up throwing 7 no-hitters in his career and had a total of 324 wins. 

7. Mookie Betts

Then there was the recent Mookie Betts trade. After multiple All-Star seasons and a year after his MVP plus World Series win, the Red Sox traded Betts to the Dodgers. The Blue Crew immediately extended Betts’ deal till 2032. In 2020, the LA Dodgers ended up winning the World Series. Simultaneously, the Red Sox collapsed to such an extent, they’ve finished last in AL East in three of the four seasons from 2020. Maybe the regrets are being felt around the Beantown.

Read more: Big Shoes to Fill: New MLB Managers Take Over Experienced Teams

Deals that made no sense: Mistakes from the Dodgers, the Giants, the Red Sox, and the Orioles

8. Joe Nathan

While these were some of the major blunders, baseball is filled with more such stories. For instance, in 2003, the San Francisco Giants traded Joe Nathan to the Minnesota Twins for A.J. Pierzynski. Nathan turned into one of the most successful closers in baseball history, while Pierzynski played just a single season for the Bay Bombers.

9. Curt Schilling

The Baltimore Orioles traded Curt Schilling to the Houston Astros for Glenn Davis in 1991. Davis hit 24 homers in three seasons and was released by the O’s in 1993. As of Schilling? Well, he ended up winning three World Series championships. 

10. Pedro Martinez

Similarly, the Dodgers traded Pedro Martinez to the Montreal Expos in 1993. Martinez won 55 games in four seasons with the Expos. In 1997, he won the Cy Young Award with a ridiculous 1.90 ERA. One wonders what could’ve been if the Blue Crew kept Martinez with them.

Read more: 2024 MLB Preview: Predictions, Marquee Matchups, Rookies to Watch, and More

What could’ve been – That’s something that all of these teams are thinking about from time to time. However, sometimes greatness shows its face after a lot of failures. Maybe that’s what happened in these situations as well.