Although he was struck out in his first major-league at-bat by Sandy Koufax in 1966, Williams did manage to get his first hit in the majors against Juan Marichal. His career as a shortstop with the Cardinals was cut short by a shoulder injury in 1969, and five years later he found work in the Angels organization as manager of their Quad Cities affiliate in the Midwest League. After two years Williams had risen to Triple-A and was named Pacific Coast League Manager of the Year in 1976 and 1979.
In 1980, Williams was hired by the Blue Jays as their third base coach. Six years later he inherited the team from popular Blue Jays skipper Bobby Cox, who had left to become GM of the Braves after leading the Blue Jays to first place in 1985. Despite his minor-league success, Williams had a tough time adapting to the majors as a manager. In his first year at the helm the team promptly slid to fourth place in the AL East, and although they were in contention for the division title the next year the Jays collapsed, finishing second to the Tigers after two crucial late-season series.
Williams alienated reigning MVP George Bell during spring training in ’88 after Williams tried to make Bell a DH. The resultant clash led to a shouting match and recurring run-ins during the year, which undercut Williams authority among his players. Williams was fired in mid-1989 and replaced with batting coach Cito Gaston. In 1990 he was reunited with Cox as the Braves third base coach.
The Red Sox hired Williams to replace Kevin Kennedy as manager after the 1996 season, bypassing more famous options like Whitey Herzog and Jim Leyland. In his first year, Williams led Boston to a 78-84 record, 20 games off the pace in an ultra-competetive AL East. In each of the next three seasons, he took the Sox to the playoffs, garnering Manager of the Year honors in 1999.
Although Williams sometimes clashed with malcontents like outfielder Carl Everett and had a reputation as a stickler for rules (he once famously benched Pedro Martinez after the ace hurler arrived late to the ballpark) there was no question that he earned the respect of his players. In September 1997, he gave oft-injured Steve Avery a start so that the left-hander could exercise a $4 million contract option for the 1998 season. But Williams often had trouble getting along with hands-on GM Dan Duquette, and was eventually fired by Duquette in August 2001 — even though his club was five games behind the Yankees in the AL East and just two games out of wild-card contention.