Could, would, or should Connor McDavid sign with the Toronto Maple Leafs Leafs?

Leafs Nation is always a stomping ground for name-brand speculation, as fans dream of high-end players coming to Toronto in one way or another. At times, this has even ended up coming true, though clearly none of them worked out well enough to deliver a Stanley Cup to the Leafs.

Even before being drafted, there has been a vision of Connor McDavid finding his way back to his hometown and suiting up for the Leafs. For most of the time, such a vision has remained quite unlikely, and that might still be the case. Still, with the final season of his contract about to begin, contemplating the possibilities of his pending UFA status is unavoidable. Let’s take a closer look at the likelihood of McDavid becoming a Leaf, as well as the potential implications of such a move.

Would?

Even though McDavid has not yet extended with the Edmonton Oilers, all signs point toward a continued relationship. The Oilers have been one of the best teams in the league over the past four seasons, appearing in two Stanley Cup Finals and three Conference Finals over that span. McDavid’s partnership and chemistry with Leon Draisaitl, an all-world talent with an incredible playoff resume, is undeniable.

With his former agent, Jeff Jackson, now serving as team president, and his former junior coach, Kris Knoblauch, serving quite effectively as head coach, McDavid has shaped the organization above him. Before even getting into his local business ventures and friendships, the Oilers have done all but win a Stanley Cup to prove their worthiness.

Despite all this, McDavid remains unextended. This might be the only fact keeping the dream alive at this point. Based on his actions so far, it seems far more likely that McDavid will stay the course. It should be expected that he will once again command the league’s highest salary, if only by a symbolic margin to appease the kinship of the players’ union. Speculation is that an extension might be done prior to the season, but with each passing day, the rumours wind shift a little bit.

Could?

If McDavid were to leave the Oilers, the Leafs might be an option. Presumably, McDavid would be leaving his cushy situation for a better one. Good teams often do not have the cap space to afford a high-end player, which narrows the field considerably. Given that only the eventual Stanley Cup-winning teams have beaten the Oilers over the past four seasons, there are few options for teams offering a better chance to win.

Of course, McDavid would make any team that he joined significantly better, but the proof of concept remains speculative. The Leafs might really test that theory, as the spectre of decades-long failure looms. They have the cap space, with almost $25M in room expected to be available next summer.

The Leafs are clearly a strong team, but with an aging blueline that is already absent a true star, it is hard to say that the future looks more promising. As much as McDavid could pick teams less equipped to deliver the championship that, presumably, fuels his decision to leave Edmonton, he could certainly find greener pastures elsewhere.

In essence, the only reason McDavid would choose the Leafs is the city of Toronto itself. This is hardly enough to go on, and the depth of that motivation is impossible to quantify. It does, however, leave the door open to the possibility until an extension is signed. With the best player and the biggest market, it should come as no surprise that McDavid to Toronto rumours will swirl.

Should?

Leaf fans are left with some retrospective questioning. Is it that the Leafs have been cursed or unlucky? Or has it been that the team has simply not been good enough? Perhaps, more importantly, are the Leafs set up to win over the course of a hypothetical McDavid contract?

These questions can delve even deeper. The character arc of this Leafs team has undergone a gradual shift under GM Brad Treliving. The concept of star players being the be-all-end-all has failed on an ideological level, and Treliving has sought to build out a more legitimate team in its stead. The Leafs will still host some high-end talent, but the mid-level of this roster should be better equipped to support them.

Signing McDavid would turn all this on its head. Of course, the Leafs will be in a better spot contractually, as the salary cap is unlikely ever to stall as much as it did during the pandemic. In fact, large increases are already confirmed for the next two seasons. Still, the salary structure of the team should give some pause. Memories of how John Tavares’ contract played out do not help either.

You have to try

Ultimately, McDavid is a good enough player that it is worth a gamble if the opportunity exists. His arrival would bring a lot of fanfare, and perhaps a renewed vigour of veterans looking to take discounts in Toronto. Perhaps slightly smarter moves could be made this time around, but perhaps the strategy itself is unwise.

Lots of the Leafs’ moves early in the Matthews era have hurt their chances now. Perhaps the equation is less about making every draft choice perfectly than it is about building through the long term on a holistic level. One might argue that the ship has already set sail based on the age of the Leafs’ core, but look no further than Matthew Knies to see what an impact a young reinforcement could make on this team.

Conclusions

McDavid is likely to stay in Edmonton. If he does want to come to Toronto, the Leafs have to try to make it happen. In all likelihood, they might never even have the chance, but if the Leafs do sign McDavid, difficult choices will ensue. Players like Bobby McMann and Anthony Stolarz should command raises, and the Leafs would have to offload elsewhere to afford them. Perhaps Joseph Woll could become available if Stolarz remains ahead on the depth chart and either Dennis Hildeby or Artur Akhtyamov build on their promising young careers, for example.

This would make the Leafs thinner, and their young players would have to provide answers all over the roster. There is little margin for error in cap hit, development, or player decay from age and injury. This is a treacherous path that Leaf fans know all too well.

If anything, exploring McDavid to Toronto only serves to emphasize the principles that Treliving is using to reshape the team. The Leafs are now a team that checks a lot of critical boxes, from a balanced defensive blueline, a strong tandem in net, size and physicality up front, and some game-breaking talent. As a collection of individuals, the Leafs might have less talent now than earlier in the Matthews era, and certainly less speculative fanfare, but as a team, they are still improving.