On December 17, 2012, Drew signed a one-year, $9.5 million contract with the Boston Red Sox, which also included $500,000 in performance bonuses. Drew had a .253 batting average, 13 home runs, and 67 RBI in the 2013 regular season. After struggling at the plate for most of the 2013 postseason, Drew homered in the decisive Game 6 of the World Series, helping the Red Sox clinch their third championship in nine years and earning his first career World Series ring.