50. Bill Barilko

“Bill Barilko disappeared that summer

He was on a fishing trip

The last goal he ever scored

Won the Leafs the cup

They didn't win another till nineteen sixty two

The year he was discovered

I stole this from a hockey card

I keeped tucked up under”

The Tragically Hip.

The subject of the legendary Canadian band's song, "Fifty Mission Cap," Bill Barilko was a strong Defenseman who logged a lot of minutes on the ice and in the penalty box.  The tough player was a large part of four Stanley Cup Championships and would twice finish in the top ten in Defensive Point Shares.  Barilko scored the game-winning goal in Game 5 of the ’51 Finals, which was the deciding game.  At age 24, Barilko was on top of the world and should have had many more years to come.

Barilko died in a plane crash on his way to a fishing trip.  As the song stated, the Leafs never won a Cup until the "year he was discovered," 1962, when the plane was found.  

The Leafs would officially retire his number 5 in 1992, likely due to the renewed attention from Gord Downie and company.