Sheldon Keefe's end in Toronto is his chance at a new beginning

I was maybe a couple months removed from my days working shoulder-to-shoulder with Sheldon Keefe in the American Hockey League when I got one of the few texts he ever sent about my work in the media. Something to the effect of “Do you need to reference your time with us in every article? Shouldn’t your analysis be good enough to stand on its own?”

I recognize the irony of cashing in that chip one more time here, and to Keefe’s point, it wasn’t always necessary. But by then I knew enough about the media business to have some sense for what can make work stand out, and my direct involvement with the Leafs organization was certainly a unique angle I have no regrets about highlighting. It offered legitimate insight, and gave my analysis credibility after I left the Toronto Marlies staff to get back into the media side of the hockey business.

Both our communication about my work and my references to our time together faded as Keefe became the head coach of the Toronto Maple Leafs, growing more comfortable in his own skin. He started caring less what was being said about himself and his teams, and more about just finding ways to win. He seemed to get a better handle on what he could and couldn’t control.

That part about “growing more comfortable in his own skin” is at the heart of Keefe’s story as the head coach of the Toronto Maple Leafs. You can’t talk about the man without talking about where he came from, and make no mistake, the early chapters of his story are tangled and dimly lit. By the time an injury cut his NHL career short, there weren’t a lot of open doors, so Keefe had to carve himself a window.

He used the money he made in just three partial NHL seasons to buy a Tier 2 team in Pembroke, where he made himself head coach and GM, and damned if he didn’t win and win and win until a path back to the OHL appeared.

Everyone was ready to look away from Keefe until he won so much they had to pay attention. He won five straight CCHL titles and eventually got hired by Kyle Dubas in the OHL to coach Sault Ste. Marie. He had success there too, and when Dubas got a quick opportunity with the Leafs/Marlies he brought Keefe along. And after more winning, it wasn’t long before Keefe was thrust into the national spotlight.

When I first got to know Keefe, he was still growing comfortable, not so much as a coach -- he was very good at that -- but at everything that came with it, particularly in Toronto.

Old players would come by the coaches offices and want to slap hands and gossip and have a laugh, but Keefe was still pretty guarded at that time. Dealing with the media was still fairly new, and it was unlikely he’d had much experience with them treating him well. The AHL also comes with a very particular age group -- boys becoming men -- and that in itself was probably challenging.

But all along, what I learned about Keefe was that he tried his butt off. Yes, he was going to put the hours in on video and numbers and scouting and all those coaching things. But what I mean is how he worked on himself.  

One summer I came back to learn he had been to several conferences, not on how to be a better coach, but how to better communicate and connect with people so he could be better at running a staff. In my second year, he documented how regularly he had personal conversations with individuals simply to make sure nobody was being overlooked.

When Dubas hired Keefe to be head coach of the Toronto Maple Leafs, he was fully equipped to handle an NHL team as a head coach. On top of his professional diligence, Keefe’s a hockey diehard who lives immersed in the sport, a sharp guy fully capable of running a bench amidst the chaos. But I bet even he looks back at his opening months with the Leafs and acknowledges how hard it was to do some of the other parts of being the head coach. The sponsor handshakes and the carefulness in press conferences and the chummy conversations with former players and small talk with a huge staff…those weren’t strengths he arrived with, but he worked to get those skills where they needed to be.

Now leaving the Maple Leafs, you can’t help but notice how many people you hear say that Keefe was “not just a good coach, but a good man.” On our radio show, Nick Kypreos has talked about having seen the Leafs' now-former head coach grow, and I see it too. He seemed more like himself more often, and that comes from a place of comfort and confidence.

Keefe will get another job coaching in the NHL, and whoever gets him is likely going to get the best version of himself yet. Away from the pressure of his home province, with all the tools he developed and honed managing a complicated team in a churning, careening news market, he should be fully equipped to be the person he wants to be.

Maybe that means he wasn’t quite ready for all he was handed when he took over the Leafs, and maybe that’s part of the reason they fell short. Maybe that same reason, more broadly applied, is a major culprit for the lack of playoff success over the past five years. A first-time president in Brendan Shanahan ended up with a young GM in Dubas who handed the keys to a young coach trying to get a team with a young core to handle the NHL’s heaviest moments.

The lift was too big an ask.

Whatever the broader reasons for the Maple Leafs' failings may be, I haven’t heard anyone say it's solely Keefe to blame for how they fell short. But while he wasn’t the problem, he wasn’t able to be the solution either, and for that sin, the Leafs have gone searching for their next head coach.

It’s tough to guess what comes next, but all I know is that when Mike Babcock left Toronto, it felt heavy, like the end.

In his final statement video, Keefe was somewhere peaceful and serene, and he looked calm, as if a weight had been lifted.

Sheldon Keefe’s end in Toronto feels like his chance at a new beginning.