In 1992, Boggs slumped to .259—one of only three times in his career that he failed to reach .300—and at the end of the season, he left the Red Sox, with whom he had spent his entire career to that point. He was heavily pursued by two teams: the Los Angeles Dodgers and the arch-rival of the Red Sox, the New York Yankees. He chose the Yankees when they added the third year to the contract that the Dodgers would not offer. Boggs went on to be awarded three straight All-Star appearances, had four straight .300-plus seasons, and even collected two Gold Glove Awards for his defense.
As a baseball player, Boggs made an appearance for the professional wrestling promotion World Wrestling Federation (WWF) in 1992. He appeared in a vignette with wrestler Mr. Perfect (Curt Hennig) in which Perfect played baseball. The two remained good friends afterward; 15 years later, in 2007, Boggs inducted the late Perfect into the WWE Hall of Fame. In the DVD The Life and Times of Mr. Perfect, Boggs related how Hennig saved his life, carrying Boggs to help after he had severely cut his leg climbing over a broken barbed wire fence during a hunting trip.