#1. Harold Ballard
For the younger fans of the Toronto Maple Leafs, you probably know of the name Harold Ballard, but don’t really understand why. With happy memories of Mats Sundin and Auston Matthews running through your head, the tough stretch of the 1970s and 1980s are fortunately not engrained in your brain.
For those of you out there that lived through the Ballard years, you probably still flinch when you hear his name. The Toronto Maple Leafs were the most successful hockey franchise, right beside the Montreal Canadiens, but that all sort of changed when Ballard took over. He was a grumpy old man that always held a grudge and it was either his way or the highway.
There were many instances over the years that still haunt fans and players, for that matter. His handling of the Dave Keon situation was awful and Keon (who was voted as the greatest Maple Leaf in history) essentially cut all ties from the Toronto Maple Leafs because of how Ballard treated him in 1975. Ballard owned his rights and refused Keon from playing for any other NHL team and it wasn’t for roughly 40 years until Keon participated in anything related to the Leafs again.
Ballard fired Roger Neilson, which enraged the fans and players and then traded Lanny McDonald away, which frustrated Leafs captain Darryl Sittler. The relationship between Ballard and Sittler worsened until he finally shipped Sittler out of town, which didn’t help the team’s record at all. In fact, under Ballard, the team was abysmal and they didn’t have a single season where they were relevant.
In terms of a business-man, Ballard knew how to make money, but fans couldn’t care less. They grew up watching successful Toronto Maple Leafs teams, but what Ballard provided was garbage. He’s easily the most hated person in team history and if it wasn’t for him, maybe the team’s last Stanley Cup wouldn’t have took place in 1967.