Red Sox Best Trades In Team History

The Boston Red Sox have a long and storied history. They've won nine World Series, including four since 2004. The first five championships came over 100 years ago. They've been around for a long time.

And they've made a lot of big trades. Some have worked wonders in the quest for a championship. Some have backfired miserably.

Here are the four best trades in Boston Red Sox history.

4. Casey Fossum, Mike Goss, Brandon Lyon and Jorge de la Rosa to the Diamondbacks for Curt Schilling (2003)

The Red Sox lost a seven-game thriller with the Yankees in the 2003 ALCS. Boston felt it was one good starter away from taking that next step, so it made a calculated risk in acquiring Schilling, who took second in NL Cy Young voting in 2001 and 2002 with the Diamondbacks but was only 8-9 in 24 starts in '03 at age 36.

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Despite the advanced age, Schilling proved to be exactly what the Sox needed. In 2004 he went 21-6 as a starter, taking second in the AL Cy Young race. In Game 6 of the ALCS vs. the Yankees and Game 2 of the World Series vs. the Cardinals, he allowed a combined one run over 13 innings. In Boston's 2004 and 2007 World Series runs, the team was 6-2 in Schilling starts.

Schilling had three more OK seasons before retiring, but the trade was a huge part of Boston's championship.

3. Hanley Ramirez, Anibal Sanchez and others to the Marlins for Josh Beckett, Mike Lowell and Guillermo Mota (2005)

This wasn't a steal as others on the list may be considered. The Red Sox had to give to get here. Ramirez turned into a three-time All-Star shortstop for the Marlins.

But the trio of players they acquired in the off-season trade proved critical in two World Series runs. Beckett went 20-7 in 2007 and took second in AL Cy Young voting and went 17-6 in 2009. Lowell batted.324 with 21 HR and 120 RBI in '07.

Mota was flipped in another off-season trade that added OF Coco Crisp.

2. Heathcliff Slocumb to the Mariners for Jason Varitek and Derek Lowe (1997)

Slocumb was a struggling closer for the Sox when they moved him to Seattle, a team in need of bullpen help, for two prospects.

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Those prospects, Varitek the closer and Lowe the pitcher, became core pieces of Boston's 2004 World Series championship, snapping the franchise's 86-year title drought.

Slocumb posted 4.13 and 5.79 ERAs in two seasons with Seattle before being traded again in 1999. Lowe led the AL with 42 saves in 2000 and moved to starter status in 2002, going 21-8 with a 2.58 ERA that season. He played until Age 40, retiring in 2013. Both

Varitek spent all 15 years of his MLB career with the Red Sox, eight of those playing at least 130 games at catcher. He was a three-time All-Star. Varitek and Lowe are both members of the Red Sox Hall of Fame.

1. Carl Pavano and Tony Armas Jr. to the Expos for Pedro Martinez (1997)

Martinez was already a big deal in Montreal. At age 24 he made his first All-Star Game in 1996, then in '97 won the Cy Young Award, going 17-8 with a 1.90 ERA with 303 strikeouts and a wild 13 complete games.

But money was always an issue in Montreal before the team relocated to Washington for the 2025 season. The Expos found a partner in Martinez to get something for him before he left for free agency.

Pedro spent seven seasons with Boston. He led the AL in ERA in four of them, strikeouts three times, in wins once and WAR twice. Martinez finished in the Top 4 of Cy Young voting seven times. He concluded his career in 2009 as one of the best pitchers in MLB history and a Hall of Famer and remains a beloved Beantown figure.

Pavano made his MLB debut in 1998 with the Expos but was OK in 2000 (8-4, 3.05 ERA in 15 game) before being traded in 2002 to the Marlins. He played 10 more seasons elsewhere. Armas pitched for Montreal for six seasons and finished his career in 2008 with a 4.65 career ERA.

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This story was originally published June 17, 2026 at 7:09 PM.