Connor McDavid, Maple Leafs star and shareholder?

The Maple Leafs are in a period of transformation.

After yet another early playoff exit, the Maple Leafs’ bosses are more equipped than ever to clean house. Why? Because John Tavares and Mitch Marner are at the end of their contracts.

By the way, Keith Pelley (CEO of MLSE, hence the Maple Leafs), in a press conference, wasn’t exactly convincing when it came time to talk about Marner’s future in town. #WewillseeHowitwillDevelop

Keith Pelley, when asked about Mitch Marner’s future as a Maple Leaf, said we’ll see how that develops/plays out in the coming weeks.

– David Pagnotta (@TheFourthPeriod) May 23, 2025

But let’s not forget the second floor. Brendan Shanahan is gone, which will leave more room for the same Keith Pelley.

Shanahan won’t be replaced since, as expected, Pelley will just take up more space. He’s been with the company for a year now, and it’s clear that Brad Treliving will be reporting to him for the rest of his career.

Keith Pelley confirms that he won’t replace Brendan Shanahan’s role and says he looks forward to working more closely with GM Brad Treliving and coach Craig Berube:

“Winning is what matters.” pic.twitter.com/eilWqu5I2q

– Chris Johnston (@reporterchris) May 23, 2025

MLSE isn’t afraid to spend, but if it’s useful. Basically, that’s what Elliotte Friedman was saying this morning on his podcast.

Pelley reiterated that he wants to win (he wasn’t going to say otherwise), but everyone knows that to do so, there will have to be drastic changes made in terms of alignment.

And that’s where we look to the future. How will Mitch Marner, who is more than ever on his way out, be replaced?

It’s all well and good to say that the club might look for Brad Marchand or Chris Kreider to change the club’s dynamic, but it’s going to take some changes in the core.

And right now, Toronto’s Howard Berger is of the opinion that the Maple Leafs are preparing a plan in case the best player in the world wants to come home in 2026.

Yes, he’s talking about Connor McDavid.

NEW TODAY: There are three names to watch for with the #Leafs in the next 14 months: Keith Pelley. Brad Marchand. Connor McDavid. Here’s the plan at #MLSE … https://t.co/iDykP2rAK9 #LeafsForever #LeafsNation

– Howard Berger (@Berger_BYTES) May 23, 2025

Should we expect McJesus to leave Leon Draisaitl and the Oilers a year from now? No, not necessarily. But that won’t stop the Maple Leafs, one of the top targets in case of a surprise, from preparing just in case.

And he added this:

But MLSE will create a seven-year plan (the maximum allowed for a free agent) to throw him off his chair – perhaps even guaranteeing him equity in the franchise after his playing career. – Howard Berger

Shares in the team, in a market as healthy as the NHL, can be an important part of the equation. And it brings to mind the Canucks and Wayne Gretzky back in the day.

The Canucks offered him 25% of the franchise to go to Vancouver and he said no. How thick I am,” he said in retrospect…

After Wayne Gretzky won the Stanley Cup, he was offered 25% of the @Canucks and a huge raise.

He declined. The rest is history.

: https://t.co/3yIOfbBF S0 pic.twitter.com/H22GaEvgbn

– Spittin’ Chiclets (@spittinchiclets) December 25, 2023

More and more, star players are buying sports teams in their retirement. A hockey player earns quite a bit less than an NFL, MLB or NBA guy.

Could this be an interesting path for McDavid? We don’t know.

extension

I don’t expect McDavid to move. But if it ever happens, it’s clear that the teams that want him will have to be ready in order to have a chance of signing him.

And since Toronto loves its local stars… #JohnTavares #StevenStamkos

SOURCES: Maple Leafs met with Steven Stamkos at MLSE headquarters Tuesday. Also present: Toronto Mayor John Tory and CEO of Canadian Tire.

– Steve Simmons (@simmonssteve) June 29, 2016

Of course, there’s no guarantee that McDavid, for whom winning is important, will want to sign in Toronto if he hasn’t won in Edmonton by 2025 or even 2026. After all, the Maple Leafs don’t have a winning culture.

But who knows…