Chicago Cubs: Theo hasn’t been shy when making moves
In 2004, Epstein traded Boston fan favorite Nomar Garciaparra and prospect Matt Murton to the Cubs, and in exchange received two Gold Glove infielders, shortstop Orlando Cabrera from the Montreal Expos and first baseman Doug Mientkiewicz from the Twins. The BoSox went on to win the World Series.
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This was a blockbuster trade, so let’s breakdown it down. The Red Sox sent Garciaparra, a solid shortstop who had amassed a career slash of .321/.367/.500 and an .867 OPS, to the Cubs.
They got back, and not from the Cubs mind you, a better defensive shortstop in Orlando Cabrera, who was a decent hitter in his own right. They also acquired Mientkiewicz.
In 2008, another multi-team deal involving a key Red Sox player was the Manny Ramirez trade that sent the mercurial outfielder to the Dodgers, bringing Jason Bay from Pittsburgh to Boston. Bay had two very good years in Boston before leaving as a free agent.
Some key points here to note. Both of the deals were multi-team deals, both included core players on the Red Sox roster, and both were made during a window of contention. A couple of other things to note, the Red Sox got back a player that took the spot of the player they traded, and both trades were made at the trade deadline.