As tough a guy as Keefe was as a player, unfortunately he's lost that edge as a coach at the NHL level, given the culture the current GM has fostered here in Toronto.
He's pretty much a baby-sitter at this point and knows the players can get him fired in basically the snap of a finger if they wanted to, similar to Babcock.
And at the same time he's basically a puppet master for an experimental analytics department that couldn't devise a way to beat the Columbus Blue Jackets in a best of 5.
So yeah, there's a lot going against him, and I'm not usually one to harp on coaches of the Leafs (it isn't an easy gig), but it's hard to really compare him to real coaches of the past who actually had a semblance of control on the team.