What Was the Worst Trade in MLB History?

By Amelia Walker Senior Content Writer Updated: 17 July 2023

Amelia Walker Senior Content Writer

Amelia Walker is a Senior Content Writer at Betting.US. She has a law degree and deep knowledge of the gambling laws in the United States. Her mission is to keep players informed about responsible gambling, while her passion for sports helps her create useful guides. Amelia has over a decade of experience in betting, which has positioned her as a trusted voice among our readers.

See Full Bio

Twitter X

Worst Trade In MLB History

• Worst Trade Deadline Dealers MLB
• What is the Worst MLB Trade Ever? Is it Babe Ruth?
• Lou Brock: The Stolen Base King
• Doyle Alexander for John Smoltz
• Randy Johnson – The Big “What If”
• Jeff Bagwell’s Surprising Journey
• Frequently Asked Questions

What is the worst trade in MLB history? That’s exactly what we’re going to reveal today, as this blog will look at some of the most infamous and controversial trades that have shaped Major League Baseball.

From awful trades to short-sighted moves that left franchises reeling, we’ll take a closer look at the trades that are still talked about today. Note that these are all simple player-for-player trades – we’ve not complicated things by adding the worst MLB draft trades into the mix!

Worst Trade Deadline Dealers MLB

In this blog, we explore the worst trade deadline dealers in MLB history, looking at deals that have had a significant impact on the league and its teams. We’ll discuss trades like Babe Ruth’s infamous move to the Yankees and the trade of Lou Brock, the Stolen Base King. We’ll also show you the interesting story about the Doyle Alexander for John Smoltz trade and talk about the big Randy Johnson trade. Let’s kick things off by looking at the worst MLB trade ever.

What is the Worst MLB Trade Ever? Is it Babe Ruth?

Babe Ruth, a name most would consider one of the greatest in MLB history, was born on February 6, 1895, in Baltimore, Maryland. The Sultan of Swat, as he was often called, was known for his exceptional skills. His ability to dominate as both a hitter and a pitcher led to him often being called one of the greatest players of all time.

Ruth began his professional career with the Boston Red Sox, where he was immediately praised for his incredibly accurate pitching abilities. He went on to help his team win three World Series titles. However, in 1919, a shocking trade sent him to the New York Yankees, and it’s often considered to be the worst MLB trade ever – for the Red Sox, not the Yankees!

This trade forever changed the face of baseball. Ruth transitioned into an outfielder and quickly became the league’s strongest hitter. He set numerous records, including 714 career home runs, and played an instrumental role in the Yankees’ rise to dominance.

Things didn’t turn out well for the Red Sox, as they suffered an 86-year championship drought, which has now become known as the Curse of the Bambino. Ruth’s trade remains one of the most significant and controversial in MLB history, with some Red Sox fans refusing to forgive the team’s owners even today.

Lou Brock: The Stolen Base King

Lou Brock, born on June 18, 1939, in El Dorado, Arkansas, was a legendary outfielder and base-stealer in the MLB. He played for the Chicago Cubs from 1961 to 1964 before being traded to the St. Louis Cardinals in a move that would shape his career – and prove incredibly controversial. With the Cardinals, Brock excelled both at the plate and on the basepaths, becoming one of the greatest base-stealers in MLB history.

Over his 19-year career, Brock stole 938 bases, setting a then-MLB record that was later surpassed by Rickey Henderson. He also recorded 3,023 hits, making him a member of the prestigious 3,000-hit club.

However, his trade from the Cubs to the Cardinals is considered one of the most lopsided trades in MLB history, as his career skyrocketed after joining St. Louis. He was a six-time All-Star, two-time World Series champion, and was inducted into the Baseball Hall of Fame in 1985.

The Cubs either missed out on a hugely valuable talent or weren’t able to bring out Brock’s full potential. Either way, this easily goes down as one of the worst MLB trade deals ever.

Doyle Alexander for John Smoltz

A pretty clear example of a move often considered the worst MLB trade ever is when John Smoltz, a promising young pitcher for the Tigers, was traded to the Braves for Doyle Alexander in 1987.

At the time, Alexander was a solid veteran pitcher, and he helped propel the Tigers to the playoffs in 1987 with a 9-0 record and a 1.53 ERA after the trade. However, his success was short-lived, and he retired in 1989. This was after his poor performance in the ALCS, going 0-2 with a 10.00 ERA, taking his postseason totals to 0-5, with a career ERA of 8.38.

On the other hand, John Smoltz became one of the best in history, and he was eventually inducted into the Baseball Hall of Fame. He was a key part of the Braves’ 1990s team, and this trade is considered by many to be one of the worst ever.

While we’re currently talking about the worst trade deadline dealers, MLB betting is a topic many of our readers will also be interested in. If you want to find a trustworthy MLB live betting site, check out our list of US-friendly bookmakers, all of which have been hand-picked by our team of online betting experts.

Randy Johnson Traded to the Mariners

In 1989, the Montreal Expos traded three of their pitchers, Randy Johnson, Gene Harris, and Brian Holman, to the Mariners. In return, they received Mark Langston and Mike Campbell.

The trade proved to be a disaster for the Expos. Langston ended up pitching in just 24 games for the Expos before he was later traded to the Angels, and Campbell didn’t even pitch one game. This caused the franchise to rapidly lose support, and they eventually moved to Washington, becoming the Washington Nationals.

Randy Johnson, on the other hand, had a great career record, and below, we’ll take a look at some of his career highlights:

Jeff Bagwell’s Surprising Journey

Jeff Bagwell, one of the MLB’s top first baseman, was born on May 27, 1968, in Boston, Massachusetts. He was first drafted by the Boston Red Sox in 1989, although in 1990, the Red Sox, seeking help for their playoff push, traded him to the Houston Astros in exchange for relief pitcher Larry Andersen. The decision would prove to be one of the worst trades in MLB history.

Bagwell’s career took off in Houston, where he played a total of 15 seasons, sporting a .297 average over the course of his career. During his time with the team, he hit a total of 449 home runs, and knocked in 1,529 RBI during his career. Bagwell performed so well that he became the best Astros player of all time, and even when 37, he was capable of performing much better than players 15 years his junior.

Anderson, while talented, didn’t bring the Red Sox success, and, in a trend that ended up happening time and time again, the team failed to win a World Series, making the trade now look completely ridiculous.