By Bailey played for the Detroit Lions in 1952 when they won the National Football League championship. In 1953, he was traded to the last place Green Bay Packers. Unhappy with the change, Bailey decided to come to Vancouver and join the fledgling BC Lions, who had just been awarded a CFL franchise. Bailey was one of the key players responsible for the success of the western team early on. In 1975, he became the first BC Lion to be inducted into the Canadian Football Hall of Fame.

Bailey became a charter member of the newly formed BC Lions in 1954 and starred with the club until his retirement at the end of the 1964 season. He began his career as a fullback in BC’s double fullback offensive backfield attack. In 1962, when the Lions dropped the double fullback position, he played outside linebacker and cornerback. Bailey wore number 88 as an offensive player and number 38 when on defense.

Bailey scored the first touchdown in BC Lions team history on August 28, 1954 versus Montreal. He also scored the first game-winning touchdown in Lions history on September 18, 1954 versus Calgary. This was the only win for the Lions during their inaugural season.

Bailey played a key decisive role in the Lions’ 1964 Grey Cup win. He was BC’s leading rusher and offensive captain for five years beginning in 1955 and twice led the Western Conference in kickoff returns.

In 1957, Bailey was named to the Western Football Conference’s all-star team as a running back. That same year, he also won the Bobby Bourne Memorial Trophy as the Lion’s “Most Popular Player.”