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Bill Quackenbush

An excellent two way Defenceman, Bill Quackenbush was one of the most disciplined players in the National Hockey League. Quackenbush rarely made mistakes on the ice. This was not just shown by his acumen with the puck, but his ability to stay out of the penalty box. He would become the first Defenceman to win the Lady Byng Trophy in a season in which he received ZERO penalty minutes. Quackenbush actually had a 131 game stretch without receiving a whistle from a referee. Although he never had the opportunity to hoist the Stanley Cup, he was a five time All Star and played in eight consecutive All Star games. It is likely though that his failure to win a Cup in the Original Six era (and his playoff PPG was a bit less than his regular season average) delayed his induction to the Hall of Fame.
A longtime President with the New York Rangers, William M. Jennings also sat on the NHL Finance Committee. Most importantly, Jennings was the Chairman of the NHL Board of Governors and the head of the Expansion Committee. Also in 1964, he was instrumental in setting up a National Hockey League office in New York City. His Rangers may never have won a Stanley Cup under his guidance, but the NHL became better because of him. As an honor to him in 1981 (shortly after he died), the William M. Jennings Trophy was created to be given annually to the Goaltender(s) who played a minimum of twenty five games on the team with the lowest Goals Against Average.

Pierre Pilote

You would not expect that someone who did not play his first organized game of Hockey until the age of seventeen to one day make the Hall of Fame, but Pierre Pilote as not your average man. Working hard to improve his skating skills to a professional level, Pilote entered the NHL with the Chicago Blackhawks in 1955 and though his debut campaign was not a successful one, he returned to Chicago vastly improved the next season.

Gordie Drillon

Although Gordie Drillon only played seven seasons in the National Hockey League, they were all productive ones for the Right Winger. Drillon played most of those campaigns in Toronto and he averaged nearly a point a game. Drillon won the NHL scoring title in 1938, which would also be the same year he won the Lady Byng Trophy. A two time First Team All Star, Drillon also won a Stanley Cup in Toronto (though it was not his best performance, as he was benched in the Finals).