5 Worst Trades in MLB History

All MLB front offices aim to make trades to improve their MLB odds of winning it all, either in the short or long term. 

Running an MLB franchise means difficult decisions are inevitable. Risks have to be taken, which occasionally backfire. 

Below, I have compiled five of the worst trades in MLB history. 

Worst Trades in MLB History

1. 1920: Red Sox Trade Babe Ruth to Yankees for Cash

Red Sox owner Harry Freese prioritized funding a play over keeping Babe Ruth in Boston. That might be the worst decision in sports history, and definitely the worst MLB trade ever. 

After starring as a pitcher with the Red Sox with 119 shutouts, Ruth scorched 54 home runs in his first season as a Yankee. 

The biggest trade in #MLB history was by the #Yankees when they got Babe Ruth pic.twitter.com/4FMj3W39Eq

— BaseballHistoryNut (@nut_history) February 5, 2022

Boston’s decision to trade Ruth began the “Curse of the Bambino” – Ruth and the Yankees dominated the sport for years to come, while the Red Sox had to wait over 80 years for their next ring. 

2. 1989: Expos Trade Big Unit to Seattle

The Montreal Expos nailed their second-round selection in the 1985 MLB draft, picking future Hall of Famer Randy Johnson. 

It went wrong from there for the Expos. They weren’t patient with Johnson, who was traded to the Seattle Mariners after just 10 MLB starts, posting a 4.69 ERA in 55.2 innings.

Johnson went on to win five Cy Young awards in his career and racked up a whopping 101.1 bWAR across stints with the Mariners, Diamondbacks, Yankees and Giants. 

3. 1987: Tigers Trade Away Smoltz

Sometimes a win-now trade is worth it. This one wasn’t. 

Detroit traded a young John Smoltz for Doyle Alexander in 1987. Smoltz was struggling in the minors and had only been drafted in the 22nd round.

Alexander helped the Tigers pick up a division title, but he posted a 10.00 ERA in the ALCS and retired at the end of 1989 after posting a 4.44 ERA.

Smoltz, of course, put together a Hall of Fame career with the Braves, winning the 1995 World Series and amassing seven All-Star appearances.

4. 2018: Pirates Give Up Farm for Archer

The Pittsburgh Pirates went all in at the 2018 trade deadline. Determined to fortify their rotation, Pittsburgh gave up a former top 10 prospect with electric stuff and two top 70 prospects for Chris Archer.

Tyler Glasnow and Austin Meadows were the core of the deal, with Shane Baz joining as a Player To Be Named Later.

Pittsburgh finished fourth in the division with 82 wins. Archer had a 4.92 ERA over 33 starts as a Pirate. Glasnow has become a top-end starter, Meadows was an All-Star, and Baz was ranked as high as eighth on some prospect lists before 2022. 

5. 1964: Cubs Trade Brock To Bitter Rivals

After amassing only 2.6 bWAR across over 300 games, the Cubs decided to trade Lou Brock to the St Louis Cardinals in 1964. 

At first, this looked like a decent deal for the Cubs, who also sent Jack Spring and Paul Toth to the Cards for Ernie Broglio, Doug Clemens and Bobby Shantz. 

Broglio, though, was the main piece of the deal for Chicago, and he had a 5.40 ERA over 213.1 innings as a Cub. 

In stark contrast, Brock was an instant hit in St Louis, posting a .915 OPS in 1964 and building a Cooperstown-worthy career. 

What Is the Biggest Trade In MLB History?

The Boston Red Sox dealing Babe Ruth to the New York Yankees is the biggest trade in MLB history. Ruth became the sport’s greatest player, finishing his career with seven World Series titles. 

Ruth’s 182.6 bWAR is 17.5 more than anyone else in the history of the sport. The Red Sox hung under the “Curse of the Bambino” for over eight decades.