Rodriguez was drafted as a shortstop by the Boston Red Sox in the second round of the 1990 amateur draft. An agreement was reached a few weeks into the 1991 season, after which he was assigned to the Class A-Short Season Elmira Pioneers. When his new teammates greeted him at the Elmira-Corning Regional Airport, the Brooklyn native was wearing clothes that bore the New York Yankees logo. After Rodriguez advanced to Class A Lynchburg Red Sox, the Red Sox realized he had greater value as a pitcher, a position he quickly began playing. He made his major league debut for the Red Sox in 1995.