Fletcher was signed by the Chicago Cubs in the 1979 amateur draft and made his major league debut with the team in 1981.

After two years in a limited role, the Cubs traded Fletcher to their intercity rival, the Chicago White Sox in 1983.

With the emergence of Ozzie Guillén in 1985, Fletcher was traded to the Texas Rangers at the end of the 1985 season.

In 1988, Fletcher became the first professional athlete in the Dallas/Fort Worth area to earn more than $1 million a year.

He was hired as an assistant hitting coach to Greg Walker on October 21, 2011.