 Theodore Samuel " Teeder " Kennedy ( December 12 , 1925 – August 14 , 2009 ) was a professional ice hockey centre who played his entire career with the Toronto Maple Leafs from 1942 to 1957 and was captain for eight seasons . He was the first player in NHL history to win five Stanley Cups and is the last Maple Leaf to win the Hart Trophy for most valuable player . He was an essential contributor to the Maple Leafs becoming what many consider as the National Hockey League 's first dynasty . He was inducted into the Hockey Hall of Fame in 1966 . He has been called the quintessential Maple Leaf and by some the greatest player in the team 's history . 
