What if… the Maple Leafs were deadline sellers

TSN’s That’s Hockey ran a segment with Craig Button and Bryan Hayes looking at the recent state of the Leafs. A large part of it focused on the perceived indifference towards winning and losing, which I don’t think is true but concede the Leafs don’t always present themselves as well as they should. The win against the Flames might have quelled some of this hysteria as well as Auston’s comments about the team needing this win.

Instead what requires a bit more exploration from that Button/Hayes segment is the notion that since the Leafs haven’t established themselves as a great team this season if they are better off cashing out at the trade deadline and refilling their prospect pool.

First off, how dare anyone even suggest that the Leafs not take full advantage of the prime window of cup contention. How dare anyone ignore the fact that the Panthers limped into the playoffs last year before going on a run to the finals. These are fair points, and the Leafs should be pushing for playoff success every year during Auston Matthews’ time in a Leafs jersey. That’s hard to argue.

What is also hard to argue is that the Leafs have a trio in Bertuzzi, Domi, and Brodie that would certainly get some looks as trade deadline rental options. You could certainly make a case for Martin Jones or Mark Giordano getting a look as well, and even Ilya Samsonov if Toronto retained half of his salary might get some eyes on him. For a team that has pretty bare cupboards when it comes to high draft picks in the next few seasons, this could be a chance to restock. Not all players would be shipped out, of course and Toronto will still have a team that is competitive enough to sneak into the playoffs, but they have the opportunity to look to the future at the same time as the present.

A lot of this mindset stems from Kyle Dubas’ history with unrestricted free agents and his own rental philosophy. This was arguably the most frustrating thing about his time as GM as his belief in the team was often to a fault and a list that includes Michael Bunting, Zach Hyman, Jake Gardiner, and Ilya Mikheyev would wind up leaving the organization without Toronto receiving a return on them. The sting wouldn’t be as strong with the players that Treliving brought in on one year deals or with TJ Brodie who has taken a step back this year but confidence not being particularly high in this iteration of the Leafs it might be worth it cash out.

The other thing to consider is that selling doesn’t equal conceding on the playoffs, nor does it mean that Toronto can’t buy as well. If the Leafs find a taker for someone like TJ Brodie, that frees up a roster spot as well as potentially brings in assets to explore someone like Chris Tanev, who should be considered an upgrade and is one of the few players rumoured to be available that would potentially change the fate of the Leafs down the stretch and in the playoffs.

If Toronto cashes out on Tyler Bertuzzi there is nothing saying they can’t turn around and pursue someone like Sean Monahan who would improve their centre depth and they could work on landing Corey Perry as a Dollar Tree alternative to Bertuzzi. (Actually, the Dollar Tree version was more successful earlier this year anyway.)

It seems like this is advocating for shuffling deck chairs or hedging bets, and that is exactly right. The deck chairs the way the Leafs have them aren’t working and there is no reason to feel confident about going all-in on this iteration of the Leafs. Trying something new and mitigating losses seems like a reasonable supporting strategy to go with and trusting that the Leafs would still have a 1 in 16 chance come playoff time to be the team that catches lightning in a bottle and goes on a run.

The Leafs won’t be sellers. With a new CEO, an MLSE Board that demands Maple Leafs playoff revenue and pressure still very much being on the likes of Brendan Shanahan the Leafs are going to push forward. Toronto as buyers is still the likely outcome. While most reasonable people will have some doubts about the current state of the Leafs, much of what this season has been about is accepting that there could be some regular season pain for potential playoff gain, allowing the Leafs to see that plan through is still what is going to occur, and reassessment will come in the offseason.