#5 – Dick Irvin
James Dickinson “Dick” Irvin Jr. spent nine seasons coaching the Maple Leafs. He was in charge from 1932 to 1940.
Though Irvin makes the list as one of the best, he is remembered best for his failures. Irvin lost in the Stanley Cup finals a record 12 times. Half of those losses were with the Leafs.
Irvin joined the Buds six games into the 1931-32 season. Art Duncan started the season, coaching the first five games. Since he didn’t win any of them (three losses and two ties), his contract was terminated and Irvin took over as the next full-time coach of the team. After the slow start with Duncan, the team found more success with Irvin. He led the club to win the Stanley Cup that year.
Irvin’s instant success was never repeated. The championship in 1932 was the only one he was able to capture with Toronto though he did win it three more times with the Montreal Canadiens. The Habs picked up Irvin after he lost in the 1940 finals. Smythe removed Irvin from his coaching duties, but recommended him to take the vacant position in Montreal.
As the head coach of the Leafs, Irvin picked up 57.5-percent of his regular-season points and won 50.8-percent of his postseason games. That was good enough for him to be named the NHL Second All-Star Team Coach five straight years while with the club.
Irvin’s impact with the Leafs was undeniable. The franchise was lucky to have had him as long as they did since Irvin is lauded as being one of the finest coaches in NHL history. He ranks fifth for the most career wins for a coach (692) behind only Ken Hitchcock (733), Al Arbour (782), Joel Quenneville (783), and Scotty Bowman (1,244). For Irvin, 31.2-percent of those wins were with the Maple Leafs.
Irvin was inducted into the Hockey Hall of Fame in 1958 though he went in as a player. In 1983, he entered the Manitoba Sports Hall of Fame where he was named Coach of the Century.