Billy "Red" Stuart played his early hockey in the Nova Scotia Senior Hockey League from 1916 to 1920. He led the league in goals and points in the 1919-1920 season and did the same in the playoffs that year while also spending the most time in the sin bin. This gained him the interest from the Toronto St. Patricks who signed him as a free agent in 1920.
Stuart made his NHL debut in the 1921-22 season and saw his first action in the Stanley Cup playoffs. The next year, Stuart won his first and only championship while helping Toronto claim its second Cup. After three more seasons in Toronto, Stuart was dealt to the Bruins in 1924. He found himself back in the finals for one last time, in 1927, but the Bruins fell to the Ottawa Senators.
The Bruins traded Stuart to the AHA's Minneapolis Millers in 1927 where he played for the next three seasons before moving around to several other teams until hanging up his skates in 1933. Stuart went back home to step behind the bench and coach in the NSSHL for the Halifax Wolverines, back in the league he began his career in.