Between April 24 and May 25, Bradley hit safely in 29 straight games, tying Johnny Damon for the fourth longest hitting streak in Red Sox history. Bradley's streak came to an end in a loss to the Colorado Rockies on May 26. At the time he started his hitting streak, he was batting .222, and when it ended, he had raised his average up to .350. This streak, along with excellent defense, earned him AL Player of the Month recognition for May. Bradley was selected to the All-Star Game, the first of his career. He started in left field, and was 2-for-2 at the plate. He ended the 2016 season with a .267 batting average, 26 home runs, and 87 RBIs, having appeared in 156 games. In the 2016 postseason, he batted 1-for-10 (.100) as Boston lost to the Cleveland Indians in the Division Series.