19. Ken Dryden:
Goalies in the NHL don’t often get much hype in the professional sports world. But Dryden undoubtedly deserved it. He was a rare professional athlete at the top of the game who had many other avenues outside of sports. Dryden stormed into the NHL by taking over net-minding duties for the Montreal Canadiens for the final six games of the regular season and the playoffs in 1971. All the team did was win the Stanley Cup, and Dryden won the Conn Smythe Trophy as the playoffs’ most valuable player.
But Dryden was far from done there. When the dust settled, he won an incredible five more Stanley Cups with Montreal. His career only lasted eight seasons. No other NHL goalie has packed that much success into such a short career. So why would he retire? Dryden felt that Montreal offered him a contract below his real value. And he didn’t need hockey anymore, becoming an attorney, author, businessman, teacher, and color commentator in addition to a member of the Canadian Parliament. Dryden is truly a man of the world, and he could have kept dominating the NHL had he wanted to.