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

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.

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