Trinidad was drafted in the 2nd round of the 1989 MLB Draft and made his major league debut with the New York Yankees in 1993. He played for the Yankees, Chicago Cubs, Colorado Rockies, Florida Marlins, and Milwaukee Brewers over 11 seasons.
Trinidad retired after the 2003 season and became a coach. He has managed in the minor leagues for the Yankees, Rockies, and Tampa Bay Rays. He was also the hitting coach for the Chicago White Sox from 2012–14. In September 2021, Trinidad managed Puerto Rico in the Tokyo Olympic qualifiers.