Full disclosure: if I was running the Toronto Maple Leafs I would have massively overpaid to get Nikita Zadorov on the roster.
The Toronto Maple Leafs had interest, but Zadorov ultimately went to the Boston Bruins. The reason I wanted him is because he's not only huge and a great shut-down defender, but he can also rush and move the puck. I think he's a late blooming star on the verge of being a top-pairing defender, and if I had the chance to do so, I would have bet heavily on it.
Brad Trelving, as we know, doesn't have that kind of risk tolerance. He's far more likely to go after an established name-brand player that he sees as a lesser risk. Ironically, making the safe player is often far worse, as the Leafs have shown.
This summer the Leafs tried to partially rebuild their blue-line and all they did was realize that they couldn't have five guys who were terrible at moving the puck (Brodie, Edmundson, Lyubushkin, Benoit, McCabe) so now they only have two (three if they get their wish and Jani Hakanpaa ends up on the team).
The Leafs blue-line is old, lacks upside, and is the most average blue-line in the NHL. In trying to improve their blue-line the Leafs just added name-brand players and called it an (expensive) day. This includes possibly the worst contract handed out in all of free-agency this year.
Since I have been writing about hockey all summer, I've probably thought about this more than most people and I cannot grasp what the Leafs were thinking when they signed Oliver Ekman-Larsson to a contract. It's so stupid that it would be funny if any other franchise did it. With the Leafs, we just sigh and go "well at least it didn't make this list!"
Here are what I think are the worst three contacts handed out this summer.