He played in Major League Baseball (MLB) for the Montreal Expos, Atlanta Braves, Cleveland Indians, Milwaukee Brewers, Los Angeles Dodgers, and San Francisco Giants between 1989 and 2005.
He was named the Most Outstanding Player of that season's Mid-Eastern Athletic Conference baseball tournament after pitching two complete games and maintaining a .643 batting average.
He made his professional debut with the Jamestown Expos of the New York–Penn League that fall and advanced quickly through the system, first appearing in the majors on August 22, 1989.
He showed steady improvement for the next few seasons, gradually developing into a star as Montreal's leadoff hitter and center fielder.
He led the National League in stolen bases in 1991 and 1992, was a member of the NL All-Star team in 1993 and 1994, and won four consecutive Gold Gloves, the first coming in 1993.
Against the Los Angeles Dodgers on July 28, 1991, Grissom caught Chris Gwynn's fly ball for the final out of Dennis Martínez's perfect game.
[4] The Expos enjoyed success on the field, but a strike ended the 1994 season before the playoffs, and after baseball resumed the team was forced to trade many of their stars for financial reasons.
Grissom was the last of the three highest-paid Expos players at the time to be traded when he was acquired by the Atlanta Braves for Tony Tarasco, Roberto Kelly and Esteban Yan on April 6, 1995.
Teams' financial motivations continued to affect the course of Grissom's career, and in March 1997, he was involved in a blockbuster trade with the Cleveland Indians.
Grissom's production declined as he spent three seasons with the struggling club, and a trade in the spring of 2001 made him a Los Angeles Dodger, sending Devon White to the Brewers in return.
On January 3, 2006, the Chicago Cubs signed him to a minor league contract and invited him to spring training as a non-roster player.
[11] Among other Atlanta-area prospects, Grissom worked with family friend Michael Harris II from his youth through his early professional career.