In 2006, Drew exercised his contract opt-out clause, forgoing $33 million over the next three years to become a free agent. Dodgers general manager Ned Colletti said in a teleconference that he was "surprised how it came down. Everything we had heard, everything that had been written led us to believe the player loved being here." This was especially a surprise because a few days before, Drew had told an LA Times columnist on how happy he was in LA and that he was looking forward to the upcoming 2007 season. Drew had a very good season, batting .284 with 20 home runs and 100 RBI. 2007–2011: Boston Red Sox On January 26, , Drew officially signed a five-year contract with the Red Sox worth $70 million. Drew's revised contract had a clause that allowed the Red Sox to opt out of Drew's five-year contract after three or four years if Drew has extensive injuries due to a previously existing problem in his right shoulder. Drew was again part of a set of four consecutive home runs on April 22, 2007, in a game against the New York Yankees, this time joining with Manny Ramírez, Mike Lowell, and Jason Varitek. He is the only player to participate twice in a string of four straight home runs, and he was the second player to go deep in each instance. Drew finished the 2007 season with a .270 batting average, 11 home runs, and 64 RBI. On October 20, 2007, Drew hit a grand slam in Game 6 of the 2007 ALCS with the Red Sox facing elimination. The home run, along with brother Stephen Drew's for the Arizona Diamondbacks, marks the third time that two brothers have both hit home runs in the same postseason. In 2008, Drew hit one of the longest home runs in Fenway Park history. According to the ESPN Home Run Tracker, it was measured at 460 feet. He finished with a .280 average, with an OBP of .408 and a slugging percentage of .519. At the end of June, Drew was named the AL Player of the Month after hitting .337 and hitting 12 home runs while taking over for David Ortiz's three-spot in the lineup while he was on the disabled list. Drew was officially announced as an AL All-Star reserve on July 6. This was Drew's first All-Star game appearance. He hit a two-run