Sporting Career
In 1887, Bain captured the Manitoba roller skating championship at the age of 13 by winning the three-mile race. He won the provincial gymnastics competition at the age of 17, and at 20, won the first of three consecutive Manitoba cycling championships. Additionally, Bain was a top lacrosse player in his home province.
Bain took up ice hockey in 1895 when he answered a classified ad placed by the Winnipeg Victorias who were looking for new players. Though he played with a broken stick held together by wire, he made the team after only five minutes of his tryout. He quickly became a star centre and leader for the Victorias, and scored the winning goal as Winnipeg were successful in their challenge against the Montreal Victorias for the Stanley Cup in February 1896. It was the first time a team outside of Quebec won the trophy. The team was greeted by a huge crowd at the Canadian Pacific Railway station when their train, decorated with hockey sticks and the Union Jack, returned to Winnipeg. They were led to a feast in their honour in a parade of open sleighs as fans gathered to celebrate the championship.
Bain and his teammates faced the Montreal Victorias in a return challenge in December 1896 that was described by the local press as "the greatest sporting event in the history of Winnipeg". Though Bain scored two goals in the game, Montreal recaptured the Cup with a 6–5 victory. The Victorias were involved in numerous further Stanley Cup challenges with Bain serving as the team's captain and manager. They again lost to their Montreal namesakes in 1898 before a record crowd of over 7,000 fans.
He scored four goals in three games in a 1900 challenge against the Montreal Shamrocks, but Winnipeg again lost the title. The Victorias challenged the Shamrocks again in 1901 in a best-of-three series. They won the series in two games as Bain scored the clinching goal in overtime of the second game. It was the first time in Stanley Cup history that the winning goal was scored in extra time. He did so while playing with a broken nose that required him to wear a wooden face mask, earning the nickname "the masked man" as a result. He led the Victorias to a successful defence against the Toronto Wellingtons in January 1902 before the team lost the Cup to the Montreal Hockey Club in March of that same year. He retired from hockey following the loss.
Throughout his sporting career, Bain earned medals in lacrosse, snowshoeing and was a national trapshooting champion in 1903. He was an avid figure skater throughout much of his life. He won over a dozen titles, the last of which came at the age of 56, and he continued to make appearances until the age of 70. He retired as a competitive athlete in 1930. "I couldn't see any sense in participating in a game unless I was good. I kept at a sport just long enough to nab a championship, then I'd try something else", said Bain of his accomplishments.
Bain was inducted into the Hockey Hall of Fame in 1949. He was elected to Canada's Sports Hall of Fame in 1971 and the Manitoba Sports Hall of Fame and Museum in 1981. He is also an honoured member of the Manitoba Hockey Hall of Fame and was voted Canada's top sportsman of the last half of the 19th century.
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