Before entering professional baseball, Benjamin played at Cerritos College and Arizona State University, where he was an All-American in his senior season.

That year he was one of four Arizona State players (including catcher Tim Spehr) named to the All-Pac-10 Conference Southern Division team by the Arizona Daily Star and to the Division I All-America Team by Baseball America.

[3][4] 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.

In October 1995, Benjamin was traded to the Philadelphia Phillies in exchange for pitcher Jeff Juden and a minor league player.

He ended his career with the Pittsburgh Pirates, playing there from 1999 to 2002 and missing the 2001 season due to injury.