Hainsworth was born in the Kew Beach area of Toronto in 1893. Hainsworth\'s family moved to Berlin, Ontario, where his father was a water commissioner for many years. After his playing days were over, Hainsworth returned to Berlin (now named Kitchener) with his wife Alma and son Bill. Bill played goaltender, like his father, and played in the Ontario Hockey Association (OHA) as a junior and later as a senior player but never a professional.\n', '

Hainsworth played junior hockey for the Berlin Union Jacks then moved up to senior hockey with the Berlin City Seniors and the Kitchener Greenshirts. One of the games he played for Kitchener against the Toronto Argonaut Rowing Club in the 1923 OHA playoffs was the first game that Foster Hewitt broadcast. By the end of the 1922–23 season, Hainsworth had played five seasons for the Greenshirts. At that time, Newsy Lalonde, manager of the Western Canada Hockey League (WCHL) Saskatoon Crescents, needed a goalie. On the recommendation of Montreal Canadiens\' part-owner Leo Dandurand, Lalonde signed Hainsworth to a pro contract of $2,500 per season with Saskatoon. Hainsworth played three seasons with Saskatoon before he was signed by Dandurand to play goal for Montreal in 1926. The Western league was in the process of folding, and Dandurand signed Hainsworth to a $6,500 per year contract before Toronto claimed him from the Western league players who were en masse moving to the National Hockey League (NHL). Dandurand had to pay $5,000 to Saskatoon for the rights to Hainsworth.\n', '

There was a need for a top goaltender in Montreal. Georges Vezina, the Canadiens goaltender, had recently died of tuberculosis. Vezina had played every game in team history from the 1910–11 NHA season until the opening game of the 1925–26 NHL season, when the illness proved too much for him. In his memory, the team decided to create the Vezina Trophy for most valuable goaltender in the NHL.\n', '

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