Doug Gilmour didn’t look fearsome on a pair of skates—being an “undersized” forward would plague him during his early career—but few players matched his killer instincts in the faceoff circle or in front of the net. The Hockey Hall of Famer from Kingston, Ontario, played for seven teams over his twenty-year career, netting 450 goals and 964 assists during the regular season and another 188 points in the playoffs, making him one of the highest-scoring centres of all time. Gilmour played a big role in the 1989 Stanley Cup victory, scoring the winning goal for the Calgary Flames. Perhaps most famously, he led the Toronto Maple Leafs to multiple winning seasons and in 1993, took them to the brink of their first Stanley Cup final in decades, only to lose out on one of the most controversial calls in hockey history.