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Biggest Boston trades of the last 20 years

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(Eric Bolte/USA TODAY Sports)

Let the discussion begin.

With Tuesday's Irving-for-Thomas deal, it’s the perfect time to talk about the biggest trades in recent Boston sports history. First, we’ll break it down by team. Then, we can discuss the order of importance. There’s been so many significant trades that’s it’s tough to pick the one that had the most impact. Either way, it’s a great discussion, so here we go.


Randy Moss. Bill Belichick has the ability to take any player and get the most out of him. That was the case with Moss. The disgruntled wide receiver arrived in New England via trade on April 29, 2007 from the Raiders in exchange for the Patriots’ fourth-round pick in 2007. The deal worked perfectly for the Patriots as they posted a 16-0 record during the regular season, while Moss recorded 1,498 yards and 23 touchdowns. The team lost in the Super Bowl to the Giants that season. Moss was eventually traded to the Vikings in 2010.

— After being a major part of the Patriots’ Super Bowl success, Richard Seymour was traded to the Raiders in 2009 in exchange for Oakland’s first-round pick, which turned into Nate Solder as the 17th overall pick.

Red Sox

— Without a doubt, the biggest trade in the last 20 years for the Red Sox involved Nomar Garciaparra. On July 31, 2004, then-Sox GM Theo Epstein pulled off a four-team trade that sent Garciaparra to the Cubs. The Red Sox acquired Doug Mientkiewicz from the Minnesota Twins and Orlando Cabrera from the Montreal Expos. The Red Sox won the World Series that season, and it wouldn’t have happened without Epstein making that trade.

— When the Red Sox acquired Pedro Martinez from the Expos on Nov. 18, 1997, the entire organization changed. Boston sent pitcher Carl Pavano and a player to be named later (Tony Armas) to the Expos in exchange for the future World Series champion and Hall of Famer. Martinez is considered to be one of the best pitchers in franchise history.

— The Red Sox don’t win the World Series in 2007 without acquiring Josh Beckett and Mike Lowell from the Florida Marlins on Nov. 24, 2005. Boston sent Hanley Ramirez, Jesus Delgado, Harvey Garcia and Anibal Sanchez to the Marlins. Beckett became the ace of the staff in ’07 and Lowell finished as the World Series MVP that same year.

— Last but not least, the Red Sox acquired Jason Varitek and Derek Lowe from the Seattle Mariners in exchange for Heathcliff Slocumb on July 31, 1997. Varitek could be considered one of the greatest captains in Red Sox history, while Lowe turned in an historic pitching performance in 2004.


— On June 28, 2007, the Celtics acquired Ray Allen and Glen Davis, along with the 35th overall pick in the 2007 NBA draft from the Sonics in exchange for Delonte West, Wally Szczerbiak and the fifth overall pick (Jeff Green). The combination of Allen and Celtics captain Paul Pierce helped produce the 2008 NBA championship.

— The Celtics also wouldn’t have won that title without the acquisition of Kevin Garnett on July 31, 2007. Boston sent Al Jefferson, Ryan Gomes, Sebastian Telfair, Gerald Green, Theo Ratliff and cash considerations, along with the Celtics’ first-round pick in 2009 to Minnesota for Garnett.


— On Nov. 30, 2005, the Bruins traded captain Joe Thornton to the San Jose Sharks in exchange for Marco Sturm, Wayne Primeau and Brad Stuart. At the time, one Bruins player commented: “We traded Joe Thornton for three players who can’t tie their skates.” The Bruins organization had grown tired of Thornton’s relaxed attitude and wanted a change. The Bruins won the Stanley Cup in 2011, returned to the final in 2013 before losing to the Blackhawks. Thornton has not won a Stanley Cup but finished as a runner-up to the Pittsburgh Penguins in 2016.

— Many believe the worst trade the Bruins have made in the last few years was dealing Tyler Seguin, along with Rich Peverley and Ryan Button, to the Dallas Stars in exchange for Loui Eriksson, Joe Morrow, Reilly Smith and Matt Fraser. The deal had nothing to do with Seguin’s on-ice performance. It was his off-ice issues that forced the Bruins to make the deal.