Any Toronto Maple Leafs fan would want to see Connor McDavid dress in the blue and white one day. After all, McDavid has been the front and center of the hockey universe ever since making his debut in the NHL back in 2015.

Because he was born in Richmond Hill, Ontario, it may not be as far-fetched as it would appear for the Toronto Maple Leafs to attempt to bring home the superstar in the coming year or two, as McDavid’s current contract is slated to expire during the 2025-26 NHL season. So then what are the possibilities that the Leafs can actually make it happen?

Well, like it or not, a lot of it will have to do with the likely conclusion of the current Stanley Cup Finals between the Edmonton Oilers and the Florida Panthers.

In recent years, McDavid and his Oilers’ club had made some solid growth in terms of postseason success, moving from falling out in the first round to to the Conference Finals and then finally to competing for the Stanley Cup.

With this now being his seventh season with the Oilers squad, frustrations have been rising for the 27-year-old great. That was why he coined the famed “it’s cup or bust” idea following their earlier than expected departure from the playoffs last season.

As a result, there’s a large disturbing yet conspicuous feeling that the current Stanley Cup Finals will play a huge role in deciding McDavid’s destiny.

If the Oilers wind up winning it all, it almost reassures McDavid that he had made the right option in sticking with group and finally fostering success.

In doing so, it would give him the belief and motivation to construct a possible dynasty with the Oilers, just like how Wayne Gretzky did when in his peak. As a result, that would destroy any dream of him of ever suiting up in a Maple Leafs uniform.

On the other hand, if the Oilers were to fail to achieve their goal in lifting the Cup, that would mean McDavid would have squandered over a decade’s time with the same core group, with each time ending up in failure.

Therefore, if they are unable to fulfill their destiny this season, it conveys an unsettling signal to McDavid that this group just won’t be able to get it done.

As a result, the potential of McDavid seeking a trade or leaving in free agency in a couple of years would then suddenly become a more likely eventuality. With Toronto being his hometown, no doubt it would be the #1 place on his list. So to have both McDavid and Auston Matthews playing together?