When Brendan Shanahan was hired as the Toronto Maple Leafs president in 2014, and for the first couple of years after that, there was more optimism around this organization than there had been in decades. And for good reason.

The Maple Leafs were bringing in a winner who brought in winners in Lou Lamoriello and Mike Babcock. But somewhere along the line, probably when Shanahan did not let Kyle Dubas go to Colorado and elevated him to the GM position, things went horribly wrong.

Shanahan's done a lot of good things, but like so many in the past who thought they could turn this franchise around, much of it was based on flawed thinking. Shanahan thought that if you loaded up on enough pure talent, had enough keen minds running the department and hired every good person out there, it would naturally translate into winning.

The thing he lacked the most? Ironically, he was bereft of Brendan Shanahans. And he doubled, tripled and quadrupled down on pure talent without getting anyone with the take-no-prisoners attitude he had as a player. Now that he's indeed leaving the Maple Leafs this summer, if he joins a different club, he'll have a chance to make up for his mistake.

Watch today's video column for a closer look and share your thoughts.

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Promo image credit: Dan Hamilton-Imagn Images