Coaches
Of the coaches available, DeBoer has the most recent success and his track record of working with great players on great teams and bringing some strategy and system mindset to his organizations makes him a worthwhile target, albeit one that teams have always felt comfortable moving on from despite doing well with them. Maybe he’s the safe choice, not the inspired one.
John Tortorella would either end up on trial for attacking a member of the Toronto media if he doesn’t attack William Nylander first. That said, he’s an established veteran coach that has a reputation for whipping disorganized lineups into shape.
Tortorella seems like a combination of Brian Burke and Randy Carlyle and that just sounds about as bad as you can get, but he’s a name that is out there and the NHL loves its retreads.
Barry Trotz isn’t available but in the event that the Predators decide that he is not a fit as the General Manager, the Leafs bringing a bag of cash to gauge his interest in coaching could be interesting. It’s hard to imagine that he’d be an in-season option for the Leafs and once you’ve expanded the search market, Trotz might not even be a front runner for the Leafs gig anyway. Trotz just seems more accessible than other dream NHL options like Jon Cooper, Jared Bednar, or Paul Maurice.
General Managers
Rob Blake, David Poile, and Ron Francis all have the distinction of being experienced NHL GMs that are more or less readily available to work and all three could just as easily be candidates for a President of Hockey Operations role as well.
Poile is the winningest GM in history and has GM of the year accolades to his name and make him perhaps the most interesting option to connect to a potential opening in Toronto. Perhaps at 75 years old, Poile doesn’t want what would come from a Toronto sports experience and would happily stay in Nashville in his advisory role. He could also represent a potential Lou Lamoriello option as someone whose best days are behind him and out of touch with the current state of the game. That isn’t likely with Poile who has much more of an adaptive approach compared to Lamoriello’s attempts at forcing his version of hockey on everyone.
Ron Francis and Rob Blake might not have Poile’s track records but Francis has made some genuine attempts building balanced lineups that are hard to play against and Blake in many ways suffered from running into Connor McDavid and Leon Draisaitl in the playoffs too many times (the Pierre Luc Dubois debacle maybe didn’t help either.)
Any of Francis, Blake, or Poile would be interesting GM options but arguably betters as President of Hockey Operations while working with someone like Brandon Pridham in the GM’s office.
A balance between the organizational knowledge that Pridham brings and the vision first approach that all three of those GMs brought to their roles might be the best option for Toronto.