After being traded on December 14, 1999, to the Boston Red Sox for minor leaguers Adam Everett and Greg Miller, he had a career high 34 home runs in . The Boston fans welcomed him at first, but their enthusiasm cooled somewhat after he was suspended for 10 days for bumping into umpire Ron Kulpa. The following year, Everett was fined for grabbing his crotch while yelling at Seattle Mariners pitcher Jamie Moyer after hitting a home run. He struggled in , with a shoulder injury hampering his performance, and ongoing controversy with the Boston media serving as a distraction to the team. One of the few bright spots for Everett that season came on September 2, 2001, when Everett came into the game as a pinch hitter and broke up a potential perfect game by Mike Mussina of the New York Yankees. Mussina had retired the first 26 Boston Red Sox and gotten two strikes on Everett before he hit a soft single to left center.