Brendan Shanahan has left the Leafs with significant challenges to surmount — on the roster and behind the scenes.

Brendan Shanahan’s time with the Maple Leafs came to a close Thursday after 11 years of tumult, progress and plateaus. Sportsnet’s Sonny Sachdeva looks back at some of Toronto’s best and worst moves of the era.

Brendan Shanahan will not be returning as president of the Toronto Maple Leafs, ending the Hall of Fame player-turned-executive’s tenure after 11 years, nine playoff appearances and no trips beyond the second round of the playoffs.