History of the National Hockey League/1917–1942/Toronto Maple Leafs/Conn Smythe

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Conn Smythe, seen enlisting with the Canadian military in 1939.

When Smythe bought the Leafs, he promised that the team would win the Stanley Cup within five years. To that end, Smythe wanted to bring in a star player to help his team. In 1930, with the Senators struggling financially due to the Great Depression, they put King Clancy up for sale. Smythe's partners could only offer $25,000 for Ottawa's defensive star, one-half of Ottawa's asking price. In an attempt to raise money, Smythe entered a thoroughbred racing horse he owned, Rare Jewel, in the Coronation Futurity Stakes at odds of 106–1. Rare Jewel won the race, earning Smythe over $15,000. Smythe then acquired Clancy for $35,000 and two players worth $15,000, which was an unprecedented price to pay for one player. It was also the only race Rare Jewel ever won.