Gilliam made his debut with the Dodgers in April 1953, with the formidable task of taking over second base from Jackie Robinson, who was shifted to the outfield and third base; he proved capable, batting .278 with a team-leading 125 runs for the NL champions. His 17 triples led the NL, and remain the most by a Dodger since 1920; he was second in the league (behind Stan Musial) with 100 walks, and third in the NL with 21 stolen bases. For his excellent season he earned NL Rookie of the Year honors, as well as The Sporting News Rookie of the Year Award.
He continued to play well during the team's Brooklyn years, batting .282 in 1954 with a career-high 13 home runs before slipping to a .249 average for the 1955 champions; he scored over 100 runs both years, as well as in 1956. With the 1956 pennant winners, he batted a career-best .300 and made his first major league All-Star team, also finishing fifth in the MVP voting; he was again second in the NL in walks (95, behind teammate Duke Snider) and steals (21, behind Willie Mays). On July 21 of that year, he tied John Montgomery Ward's 1892 major league record of 12 assists in a game. In the Dodgers' last season in Brooklyn in 1957, he batted .250 but led the NL in putouts and fielding percentage and again finished second behind Mays in stolen bases.
Gilliam was named a coach after the 1964 season, and intended to end his playing career, but team injuries resulted in his seeing substantial play at third base in 1965 and 1966, with the team again winning the NL championship in both seasons. In 1965 he was part of the major leagues' first all-switch-hitting infield, with shortstop Wills, first baseman Wes Parker and second baseman Jim Lefebvre. On September 5, Gilliam hit a 2-run pinch triple in a road game against the Houston Astros, giving the Dodgers a 3–2 lead in the 9th inning; the Los Angeles Rams, playing a preseason game against the Philadelphia Eagles at the Coliseum, were playing so poorly despite their 10–0 win that the biggest cheer from the stands came from people listening to portable radios tuned to the Dodger game who cheered when Gilliam got the hit.
He finally retired as a player following the 1966 season with a .265 career batting average, 1889 hits, 1163 runs, 65 home runs, 558 runs batted in, 304 doubles, 71 triples, 1036 walks and 203 stolen bases over 14 seasons.
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