He had four brothers and five sisters. The family grew up in the neighbourhood of Davenport, which his brother Charlie described as "one of Toronto's higher class slums". His father was a teamster, and struggled to earn enough money to support the family. In the winter, he ploughed the snow off outdoor skating rinks to earn additional money. Conacher left school after the eighth grade to go to work and help support his siblings. For ten hours a day, he hauled sod, earning an extra dollar a week for his family. All ten children were encouraged to participate in sports by the principal of Jesse Ketchum School, who felt that such pursuits would keep his students from getting into trouble. Conacher discovered that he was among the better players in any sport he tried, and quickly became a star at Canadian football, ice hockey and lacrosse. He realized his athletic ability could offer an escape from poverty. Amateur career Conacher was a prolific athlete, excelling in numerous sports at the same time. He played with 14 different teams during his teenage years, winning 11 championships. He was 16 years old when he won the Ontario lightweight wrestling championship, and at 20 won the Canadian amateur light-heavyweight boxing championship. In 1921, he fought, and was knocked out by heavyweight champion Jack Dempsey in an exhibition match. One year he famously hit a triple to win the Toronto city baseball championship, then rushed to the other side of the city to find his lacrosse team trailing 3–0 in the Ontario provincial final. He scored four goals and an assist to lead them to a comeback victory. Football Rugby football was the first sport Conacher played, and it was his favourite. He first played organized football at the age of 12 as a middle wing with the Capitals in the Toronto Rugby Football League. He played four seasons with the team between 1912 and 1915, during which the Capitals won the city championship each year. He won the Ontario championship as a junior with the Toronto Central YMCA in 1918, and in 1919 moved up to the intermediate level. With the intermediate Capitals, he was moved into an offensive role as a halfback. He excelled in the role, and his team reached Ontario Rugby Football Union (ORFU) final. In that final, the Capitals' opponents from Sarnia made stopping Conacher their priority, a strategy