Top 25 MLB trades of all time

NEW YORK, NY - APRIL 09: Pitcher Noah Syndergaard #34 of the New York Mets delivers a pitch against the Miami Marlins during the first inning of a game at Citi Field on April 9, 2017 in New York City. (Photo by Rich Schultz/Getty Images)
NEW YORK, NY - APRIL 09: Pitcher Noah Syndergaard #34 of the New York Mets delivers a pitch against the Miami Marlins during the first inning of a game at Citi Field on April 9, 2017 in New York City. (Photo by Rich Schultz/Getty Images) /
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NEW YORK, NY – JUNE 14: Pedro Martinez #45 of the Boston Red Sox pitches during the game against the New York Yankees at Yankee Stadium on Wednesday, June 14, 2000 in the Bronx Borough of New York City. The Yankees won the game 2-1. (Photo by Rich Pilling/MLB Photos via Getty Images)
NEW YORK, NY – JUNE 14: Pedro Martinez #45 of the Boston Red Sox pitches during the game against the New York Yankees at Yankee Stadium on Wednesday, June 14, 2000 in the Bronx Borough of New York City. The Yankees won the game 2-1. (Photo by Rich Pilling/MLB Photos via Getty Images) /

7. Pedro Martinez to the Red Sox, 1997

  • Red Sox get: Pedro Martinez
  • Expos get: Carl Pavano, Tony Armas

Staring down Pedro Martinez’s free agency with no real chance to re-sign him, the Montreal Expos did the smart thing and traded him for two highly-touted pitching prospects from the Boston Red Sox farm system. Martinez never went to free agency as the Red Sox were able to keep him. Pavano and Armas never developed into top-of-the-rotation starters, but did both have decent MLB careers.

Martinez went from a very good pitcher with the Expos to one of the all-time greats with the Red Sox. From 1998 to 2003, he went 101-28 with a 2.26 ERA, 2.24 FIP, 212 ERA+ and 11.2 strikeouts per nine. Martinez won the pitching Triple Crown in 1999 with a 23-4 record, 2.07 ERA and 313 strikeouts. He had a 1.39 FIP that year and got nearly half of his outs via the strikeout. If possible, he was even better in 2000, finishing with a 1.74 ERA in the height of the Steroid Era. His ERA+ of 291 is the best of the modern era, and is still almost better than Tim Keefe’s mark of 293, which was set in 1880.

Besides the dominant pitching, Martinez brought a swagger that the Red Sox had been missing for decades. He was never one to back down, and just attacked hitters with a ferocity seen in few pitchers in the history of the game. Martinez made the Red Sox relevant again on the national stage, injected life back into their rivalry with the New York Yankees and helped lay the groundwork for the end of the Curse of the Bambino.

From a trade standpoint, this wasn’t a bad deal for the Expos. Pavano and Armas both had some flashes during their time with the franchise. This is just part of the typical life cycle for a small-market team. It’s almost always impossible to get back equal value when dealing a Hall of Famer like Pedro Martinez.