Though Bright played strictly defense as a linebacker in his first year with the Eskimos, he played both offense (as a fullback) and defense for two seasons (1955–1956), and played offense permanently after that (1957–1964). He, along with teammates Rollie Miles, Normie Kwong, and Jackie Parker, helped lead the Eskimos to successive Grey Cup titles in 1954, 1955, and 1956 (where Bright rushed for a then Grey Cup record of 169 yards in a 50–27 win over the Montreal Alouettes). In 1957, he rushed for eight consecutive 100-yard games, finishing the season with 1,679 yards. In 1958, he rushed for 1,722 yards. In 1959, following his third straight season as the Canadian pro rushing leader with 1,340 yards, Bright won the CFL's Most Outstanding Player Award, the first black athlete to be so honored.