Bailey's NHL career officially began with the Boston Bruins, where he played as a left winger. During his time with the Bruins, he was part of a team that included legendary players such as Bobby Orr and Phil Esposito. Bailey contributed to the Bruins' success in the early 1970s, including their Stanley Cup victories in 1970 and 1972. Although not a high-scoring player, his role on the team was valued for his work ethic and ability to support his teammates.
After his tenure with the Bruins, Bailey was traded to the Detroit Red Wings in 1973. His time with the Red Wings was relatively short, and he soon found himself moving to the St. Louis Blues. Bailey's career continued with the Washington Capitals, where he played from 1974 to 1976. The Capitals were a new franchise at the time, and Bailey's experience was an asset to the young team.
In 1976, Bailey joined the Edmonton Oilers, who were then part of the World Hockey Association (WHA). Playing in Edmonton was a homecoming of sorts, as he had previously played junior hockey in the city. Bailey's presence on the Oilers helped the team during its formative years in the WHA, and he remained with the team until the league's merger with the NHL.
Throughout his career, Bailey was known for his tenacity on the ice and his ability to adapt to different teams and playing styles. His career statistics include over 500 games played in the NHL and WHA, with a modest number of goals and assists. While he may not have been a star player, his role as a team player was appreciated by his coaches and teammates.
After retiring from professional hockey, Bailey transitioned into a scouting role. He worked as a scout for the Edmonton Oilers, contributing to the team's success in the 1980s. His knowledge of the game and ability to identify talent were valuable assets to the Oilers' organization.
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