8. Bill Masterton
Bill Masterton was from Winnipeg, Manitoba and was signed by the Montreal Canadiens right out of college in 1961.
He was an All-American player and was a great addition to the team. He spent most of his years playing in minor league and then quit for some time to work for a corporation.
On January 13, 1968, the North Stars were playing the Oakland Seals. Masterton had the puck and was close to scoring, but passed the puck.
Masterton was checked by two players of the Seals' team and immediately feel backwards on the ice, his head slamming against it.
He died shortly after due to a massive brain hemorrhage. It was so bad that even doctors couldn't operate.