They appear to have made such a move this past weekend, when the Sox shipped Adrian Gonzalez, Josh Beckett, Carl Crawford and Nick Punto to the Los Angeles Dodgers in exchange for James Loney and four prospects.
The deal is historic in its magnitude, and it could very well be the biggest trade the team has made since the Sox infamously traded Babe Ruth to the Yankees.
However, the Sox have shown a proclivity for bold moves in the recent past. In 2005, the team traded can't-miss prospect Hanley Ramirez and Anibal Sanchez to the Marlins in exchange for Mike Lowell and Josh Beckett. This was a rare example of a trade that seemed to work out well for both sides. Sanchez threw a no-hitter for the Marlins and Ramirez developed into the superstar he was expected to, while Beckett and Lowell led the Red Sox to a World Series victory in 2007.
The year before that deal was made, the Red Sox may have made their boldest move of all by trading Nomar Garciaparra at the trade deadline. In return, they acquired a trio of players in Orlando Cabrera, Doug Mientkiewicz and Dave Roberts that played huge roles in helping the Red Sox capture their first World Series title in 86 years.
In 2003, the team also pulled the trigger on a big deal, landing Curt Schilling in exchange for Brandon Lyon and prospects. That wasn't the first time that the Sox had traded prospects for an elite pitcher, though, as they also demonstrated in 1997 when sending Tony Armas Jr. and Carl Pavano to the Montreal Expos for Pedro Martinez.
Of course, it would be impossible to discuss the biggest trades in the post-Babe era without mentioning the team's storied exchange of Heathcliff Slocumb for Jason Varitek and Derek Lowe. That is the one pointed to by many as one of the best Red Sox deals of all time — is it the biggest?