Wills was a star football quarterback and baseball pitcher for Cardozo High School (Washington, D.C.), and was signed to a contract by the National League Brooklyn (later Los Angeles) Dodgers in 1950. He batted both right- and left-handed and threw right-handed. He played for their minor league teams (1951–59) as a second baseman before he was called up to the parent club in 1959, where he played shortstop until he was traded to the Pittsburgh Pirates (1967–68) and drafted in the expansion of the league by the Montreal Expos (1969). He was traded back to the Dodgers in that year and played with them until his retirement in 1972.

Wills led the league in stolen bases in six seasons (1960–65), establishing a season record of 104 in 1962 (surpassed in 1974 by Lou Brock (Brock, Lou)'s 118). After his retirement as a player Wills managed four seasons in the Mexican League during the 1970s, served as base-stealing instructor for five major league clubs in spring training, and did some sports announcing. He was manager of the American League Seattle Mariners (1980–81).