Billy Reay

Montreal's two-time Cup winner who coached the Maple Leafs to last place in 1957–58, then won 500 games in Chicago.

William Tulip Reay (August 21, 1918 – September 23, 2004) was a Canadian professional ice hockey player and coach. He spent ten seasons in the NHL as a player, from 1943 to 1953, and won two Stanley Cups with the Montreal Canadiens—in 1946 and 1953. That second championship was his last game as a player. After retiring, Reay became head coach of the Toronto Maple Leafs in 1957, but the team finished last in the six-team league.

He was fired midway through the 1958–59 season. Reay later returned to the NHL as head coach of the Chicago Black Hawks in 1963, a job he held for fourteen years. He led Chicago to the Stanley Cup Final three times (1965, 1971, and 1973) but never won a championship as a coach. Still, he finished his career with more than 500 wins, becoming only the second coach to reach that mark with a single team.

At the time of his retirement, he ranked second in NHL history in total victories. Today, he remains one of thirty coaches with 500 or more wins. Reay died of liver cancer in Madison, Wisconsin, at age 86.