Best MLB trades in history: Deals that changed baseball

The Curse of the Bambino, Mookie jumping ship, and so many other stories tell the tale of baseball. The MLB is known to make plenty of deals at the deadline, as some teams become buyers and others sell the farm with hopes of a brighter future. A major trade in the middle of the season can completely change the prices in prediction markets.

But what are the biggest MLB trades of all time that define the history of the MLB?

Biggest trades in MLB history

1. Babe Ruth from Boston to New York

A league-defining trade, a massive stake driven between two franchises who would later become rivals, and a curse that would last nearly 100 years.

• To the New York Yankees: Babe Ruth
• To the Boston Red Sox: $100,000 in cash plus a $300,000 personal loan to Red Sox owner Harry Frazee.

The Babe Ruth trade was well worth the money for the Yankees, as he shattered his own single-season homerun record by hitting 54 in 1920 and 59 in 1921, bringing the Yankees multiple championships during his tenure in pinstripes.

“The Curse of the Bambino” would sink in for the Boston Red Sox, as they would not win another World Series for 86 years after this deal.

1. Pedro Martínez from Montreal to Boston

Pedro Martinez won the 1997 NL Cy Young Award and then was immediately shipped away to Boston. 

• To the Boston Red Sox: RHP Pedro Martínez (coming off his 1997 NL Cy Young Award season)
• To the Montreal Expos: Pitching prospects Carl Pavano and Tony Armas Jr.

Despite winning the Cy Young with the Expos, Martinez and the club could not see eye-to-eye on a contract extension. Shortly after the trade went official, Martinez signed a six-year, $75 million contract extension, a record for its time. 

Martinez became a franchise player for Boston, with a 117-37 record and a 2.52 ERA over seven seasons. He was a major part of the 2004 Boston Red Sox championship team that broke the aforementioned “Curse of the Bambino” and he won two AL Cy Young Awards in 1999 and 2000. In 2015, the same year he was inducted into the National Baseball Hall of Fame, the Red Sox retired his number 45.

1. Jeff Bagwell from Boston to Houston

In 1990, the Red Sox traded a minor-leaguer Jeff Bagwell to the Astros in exchange for reliever Larry Anderson. A trade that would later be regarded as one of the most lopsided trades ever.

• To the Houston Astros: 3B Jeff Bagwell
• To the Boston Red Sox: RP Larry Andersen

The Red Sox wanted some reliever help for a late season playoff push, but they fell short of a championship, extending their drought at the time. Anderson pitched well, but left via free agency after the season. This is one of the worst trades in MLB history in terms of one team benefitting over another.

Bagwell found his place in Houston switching from third base to first base. He would spend the rest of his 15-year career in Houston, winning the 1991 NL Rookie of the Year, the 1994 NL MVP Award, four All-Star selections, and was inducted into the National Baseball Hall of Fame in 2017.  This is also an example of a team trying to swing their price in the market prior to a playoff push.

1. Chris Sale from Chicago to Boston

The Boston Red Sox once again find themselves making a major headline with a lopsided midseason trade, this time one that goes in their favor. 

• To the Boston Red Sox: SP Chris Sale
• To the Chicago White Sox: INF Yoan Moncada, SP Michael Kopech, OF Luis Alexander Basabe, SP Victor Diaz

Chris Sale was the missing piece to the Red Sox’s 2018 World Series run closing out Game five with a strikeout in a signature moment that would win them a championship. He led the AL in strikeouts in 2017, made three All-Star teams and was the Cy Young runner up in 2017.

Most of the players going to Chicago played several seasons for the team, but it never amounted to a championship.

1. Mookie Betts from Boston to Los Angeles

Three teams came together on a blockbuster deal that would send Boston’s cornerstone player Mookie Betts to Los Angeles.

• To the Los Angeles Dodgers: OF Mookie Betts, SP David Price, and cash considerations from the Red Sox, along with Brusdar Graterol, Luke Raley, and a draft pick from the Minnesota Twins.
• To the Boston Red Sox: OF Alex Verdugo, SS Jeter Downs, and C Connor Wong from the Dodgers.
• To the Minnesota Twins: SP Kenta Maeda and cash from the Dodgers.

Mookie Betts, who won the 2018 World Series with the Red Sox, was looking for a new deal and Boston was unwilling to give it to him. When he arrived in LA, Betts signed a historic 12-year, $365 million contract extension. He has since won three World Series with the Dodgers.

Verdugo, Downs, and Wong would all be off the Red Sox’s roster within the next three years. 

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FAQs about best MLB trades in history 

What were the biggest MLB trades in history?

Babe Ruth to the Yankees and Mookie Betts to the Dodgers.

What were the worst trades in MLB history?

Sending Jeff Bagwell to the Astros is one of the most lopsided MLB trades in history.

Why is the Babe Ruth trade so famous?

It spawned the “Curse of the Bambino” that held the Red Sox championshipless for nearly 100 years and birthed the Yankees-Red Sox rivalry.

How long does it take to judge whether a baseball trade was successful?

This depends on the trade made. If it’s for a playoff push, then you can tell by the end of the season, but if it's for rebuilding purposes, you have to give the trade a few years to decide it’s success.

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