Benjamin was a third-round draft pick of the San Francisco Giants in June 1987, and by April 1989 he was playing for the Giants' Triple-A affiliate, the
Phoenix Firebirds. He was said to be playing sensationally at shortstop but experiencing lower back pain. Benjamin made his major league debut with the Giants on July 7, 1989, and he played with the team through 1995, never appearing in more than 68 games in a season. On June 14, 1995, he tied a Giants single-game record with six hits. This was part of a stretch in which he tied the major league record for most hits in two consecutive games with ten, set a major league record for most hits in three consecutive games with 14, and tied another record for most hits in four consecutive games with 15. In October 1995, Benjamin was traded to the Philadelphia Phillies in exchange for pitcher
Jeff Juden and a minor league player. After one season there, he was granted free agency. He signed one-year contracts with the Boston Red Sox in 1997 and 1998. With the 1998 Red Sox, Benjamin appeared in a career-high 124 games and hit for a career-high .272 batting average. He ended his career with the Pittsburgh Pirates, playing there from 1999 to 2002 and missing the 2001 season due to injury. ==Later life==