He started out in Kirkland Lake where the boys at his school would frequently take on Honoured Member Dick Duff's gang one day and Ralph Backstrom's the next. Hillman soon began to rise to the top of the town and on to the OHA where he played for the Windsor Spitfires and the Hamilton Tiger Cubs.
In 1955, Hillman launched his NHL career with the Detroit Red Wings where he played in three playoff games en route to a Stanley Cup win. He made it to the finals again the following season and then settled into a familiar pattern of bouncing between the AHL and the NHL.
Hillman's basic steadiness on the blueline made him a desirable commodity for slotting into the gaps opened up as a result of injuries and slumps. In 1957, he put in three seasons with the Bruins and then spent most of the sixties toiling for the Leafs and the Rochester Americans. His reward for Leafs loyalty came in the form of two Stanley Cup wins, one in 1964 and the other in 1967.
By the late 1960s, Hillman's nomadic tendencies continued with brief stints in Minnesota, Montreal, Philadelphia, Los Angeles and finally, in Buffalo. n 1973, he jumped to the WHA's Cleveland Crusaders before having his career cut short in Winnipeg as a result of a contract dispute with the Jets. After the ugly squabble was resolved, the club hired him as their head coach for two additional seasons.
By the end of his well-travelled career, Hillman had captured a remarkable six Stanley Cups through 1955-69 with the Toronto Maple Leafs and Detroit Red Wings.
Courtesy of the Hockey Hall of Fame