Brendan Shanahan era ends in Toronto after another Maple Leafs' letdown

Shanahan's legacy with Toronto is complicated because it brought a lot of good, especially in the beginning. 

When he joined the front office, the Maple Leafs were the joke of the league. They struggled to find their way and mostly floated aimlessly around in circles like a directionless ship. 

Shanahan helped change that. 

He brought a sense of direction and began rebuilding. In three straight drafts from 2014-16, the Maple Leafs landed William Nylander, Mitch Marner and Auston Matthews, while also adding John Tavares in free agency in July 2018.

Those players, eventually known as the "core four," helped turn the Maple Leafs into a consistent contender, but that ended up being their ceiling. Those playoff appearances typically resulted in frustration and embarrassment instead of glory. 

Despite being among the highest-paid forwards in the league, the aforementioned core group has consistently come up short in the playoffs. In nine playoff appearances since the start of the 2016-17 season, the Maple Leafs have won only two playoff series and never won more than seven games in a single playoff run. They never even got halfway to a championship (16 wins) in one year. 

The forwards deserve criticism for their lack of offense in big games, and the front office deserves criticism for consistently running it back with the same core group. Not supplying them with the right support players or being willing to make tough changes ultimately cost them. 

Shanahan was put in charge of the organization to help bring the Stanley Cup back to Toronto for the first time since 1967. He never got them over the hump, and that is a massive letdown, especially considering the high expectations at the start of his tenure. 

The longer the Maple Leafs' drought gets, the more necessary change becomes. More must be done regarding Toronto's on-ice roster in the coming weeks and months.