Stanley played college baseball for the University of Florida, and thereafter, he played professionally with the Texas Rangers (1986–1991), New York Yankees (1992–1995, 1997), Boston Red Sox (1996–1997, 1998–2000), Toronto Blue Jays (1998) and Oakland Athletics (2000).

Stanley hit more than twenty home runs in a season three times during his career.

His best all-around season at the plate came in 1993 with the Yankees, when he hit .305 with twenty-six homers and eighty-four RBI.

Following his retirement as a player, Stanley was hired to serve as bench coach for the Red Sox during the 2002 season.

Stanley currently serves as an assistant baseball coach for the Lake Highland Preparatory School in Orlando, Florida.