Bennett was originally drafted by the Philadelphia Phillies on June 4, 1990. After a few seasons with their minor league affiliates, Bennett was called up to make his MLB debut on September 24, 1995, playing only a single game that year.

Following the 1996 season, Bennett was released by the Phillies and signed with the Boston Red Sox on February 10, 1997. After spending the entire 1997 season in the minors, he was released and re-signed with the Philadelphia Phillies on December 27, 1997.

Bennett continued with the Phillies for the next three seasons, splitting his time between the Phillies and the minors. On July 23, 2001, he was traded to the New York Mets. Bennett only played one game for the Mets before he was traded again on August 23, 2001 to the Colorado Rockies.

Bennett played 90 games with the Rockies during the 2002 season, then was released and signed with the San Diego Padres on December 23, 2002. He shuffled between several teams over the next few years, playing for the Milwaukee Brewers in 2004, the Washington Nationals in 2005 and the St. Louis Cardinals in 2006 and 2007.

On December 13, 2007, Bennett was named in the Mitchell Report for alleged steroid use. Four days later he signed as a free agent with the Los Angeles Dodgers.

1. Full name: Gary David Bennett Jr.
2. Born: April 17, 1972
3. Birthplace: Waukegan, Illinois
4. Made MLB debut with the Philadelphia Phillies
5. 2003: First time he received over 300 at bats
6. 2006: On the 2006 World Series Roster for the St. Louis Cardinals
7. One of many players named in the Mitchell Report