The 30 worst trades in MLB history

Oct 18, 2015; New York City, NY, USA; Chicago Cubs starting pitcher Jake Arrieta throws a pitch against the New York Mets in the first inning in game two of the NLCS at Citi Field. Mandatory Credit: Anthony Gruppuso-USA TODAY Sports
Oct 18, 2015; New York City, NY, USA; Chicago Cubs starting pitcher Jake Arrieta throws a pitch against the New York Mets in the first inning in game two of the NLCS at Citi Field. Mandatory Credit: Anthony Gruppuso-USA TODAY Sports /
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Jul 28, 2015; Boston, MA, USA; Hall of Fame player Pedro Martinez throws out the first pitch under the watchful eye of former Boston Red Sox players Tim Wakefield, (left) Jim Rice, Carlton Fisk and Carl Yastrzemsk during his number retirement ceremony before the game against the Chicago White Sox at Fenway Park. Mandatory Credit: Greg M. Cooper-USA TODAY Sports
Jul 28, 2015; Boston, MA, USA; Hall of Fame player Pedro Martinez throws out the first pitch under the watchful eye of former Boston Red Sox players Tim Wakefield, (left) Jim Rice, Carlton Fisk and Carl Yastrzemsk during his number retirement ceremony before the game against the Chicago White Sox at Fenway Park. Mandatory Credit: Greg M. Cooper-USA TODAY Sports /

14: Pedro Martinez to the Red Sox

The trade: Boston received Pedro Martinez

Montreal received Carl Pavano and Tony Armas Jr.

Spoiler alert: this isn’t the only time Pedro Martinez appears on this list. Not long after he became a prized acquisition by the Expos, Pedro Martinez was dealt to the Red Sox in 1997. Martinez was signed to a monster 6-year, $75 million contract which he paid off right away.

In his first season with the Red Sox, he won the Cy Young, and in his second season, he won the pitchers’ Triple Crown by leading the league in ERA (2.07), strikeouts (313), and a 23-4 record. However, among all of his accomplishments, what Red Sox fans will remember most is Martinez leading the team to their first World Series in 86 years, effectively ending the Curse of the Bambino.

What did Montreal receive in return? A rookie in Carl Pavano who pitched to a total record of 24-35 and a 4.83 ERA with the Expos. Tony Armas’ time in Montreal was overshadowed due to various injury concerns, and he filed for free agency in 2006. All told, the Expos never recovered from this deal, as it made the team so bad they had to relocate to Washington.

Next: 13: Paul Konerko to the White Sox