Playing Career
Stuart first joined a senior hockey team when he spent the winter of 1895–1896 with the Rat Portage Thistles, a team in northwestern Ontario. Along with his brother Bruce, Stuart joined the Ottawa Hockey Club of the Canadian Amateur Hockey League (CAHL) for the 1899 season. He played the 1900 season for Ottawa, captaining the team. Through his father's business contacts, Stuart got a job in Quebec and moved there in 1900; upon arriving there he joined the Quebec Bulldogs, also of the CAHL. He scored seven goals in fifteen games with the team over the next two seasons.
In 1902, the Pittsburgh Bankers of the Western Pennsylvania Hockey League signed Stuart to a professional contract; this was disputed between the Bankers and the Pittsburgh Victorias, who also claimed him. Eventually the Bankers won the dispute and kept Stuart; the following year they would also sign Bruce. Stuart was offered a salary of US$15–20 per week, plus steady income from a day job in Pittsburgh. Stuart scored seven goals and had eight assists and was named the best cover-point in the league in 1903.
After one season in Pittsburgh, Stuart moved to the Portage Lakes Hockey Club, a team in northern Michigan, for the 1903–1904 season and played in fourteen exhibition games, finishing fourth on the team with thirteen goals scored. With the formation of the International Professional Hockey League, Stuart left Portage Lake for the Calumet Miners, where he accepted the positions of coach and manager, in addition to playing cover-point, for $1,800. He scored eighteen goals for Calumet in 1904–1905, helped the team with the league championship and was named to the end of season all-star team as the best cover-point in the league.
On December 11, 1905, before the start of the 1905–06 season, Stuart was suspended from the league after the western teams complained that he had won too many championships and was too rough for the league. He was reinstated by the league on December 30, and joined the Pittsburgh Professionals. After Pittsburgh finished their season, Stuart joined Calumet for one game so they could try to win the league championship, which they lost to the Portage Lakes Hockey Club. Once again he was named best cover-point in the IPHL as he scored eleven goals. A big man with a fluid skating stride, he was considered the finest defenceman of his era for his outstanding play on both offence and defence.
As the IPHL convinced players to move to the United States and get paid to play, hockey teams in Canada were forced to match the salaries in order to keep their players. Stuart, who was unhappy playing in Pittsburgh because of the violence involved in games, heard from Dickie Boon that the Montreal Wanderers, defending Stanley Cup winners, of the Eastern Canada Amateur Hockey Association (ECAHA) were willing to make Stuart the highest paid player in hockey if he were to join the team. On December 13, 1906, Stuart had a letter published in the Montreal Star that detailed his problems with the IPHL. Stuart's chief concern was the officiating; he said they "don't know how to run hockey over here, the rink people appoint the most dumb and incompetent referees that could be found." In December 1906 Pittsburgh refused to play a game against Michigan Soo, claiming they did not like the choice of referee. While a common problem in the IPHL, Pittsburgh's management believed Stuart was behind the action, and released him from the team. No longer bound to any team, Stuart joined the Wanderers; his first game with the team was watched by 6,069 fans. He took part in the Wanderers' Stanley Cup challenge against the New Glasgow Cubs, a team from Nova Scotia, on December 27 and 29, 1906, and along with teammates Riley Hern, Frank Glass, Moose Johnson and Jack Marshall, became the first professional hockey players to compete for the Stanley Cup.
"They could not offer me money enough here to go through what I went through last year in this league. Everybody had a slur at me and I could not lift my stick off the ice. That is a fact. I never took my stick off the ice, except in shooting, all winter, and never checked a man with the stick."
Excerpt from letter written by Stuart to the Montreal Star on December 13, 1906 detailing his issues with the IPHL.Stuart did not escape violence in the ECAHA. On January 12, 1907, the Wanderers faced the Ottawa Senators, a game the Wanderers ultimately won 4–2. Charles Spittal of Ottawa was described as "attempting to split Cecil Blachford's skull", Alf Smith hit Stuart "across the temple with his stick, laying him out like a corpse", and Harry Smith cracked his stick across Ernie "Moose" Johnson's face, breaking Johnson's nose. Stuart was commended for his actions during the game; it was said that he neither flinched nor retaliated, even after bearing most of the hits. At a league meeting on January 18, the Montreal Victorias proposed suspending Spittal and Alf Smith for the season in response to their actions, but this was voted down and the president of the league, Fred McRobie, resigned. The next time the Senators visited Montreal for a game, the police arrested Spittal, Alf and Harry Smith, leading to $20 fines for Spittal and Alf, and an acquittal for Harry. Even with the persistent violence, Stuart helped the Wanderers to an undefeated season; they then accepted a challenge from the Kenora Thistles for the Stanley Cup. The Thistles won the series, held in January, but lost a rematch between the teams in March, giving the Cup back to the Wanderers. Stuart participated in both challenges, and though did not score a goal in any of the four games, he was said to have played the best game of his career in the first game of the series, even with a broken finger. Regarded as the most important player on the Wanderers, Stuart was said to know how to play every position on the ice, and passed his knowledge of the game onto his teammates.
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