It's ironic how Canadian fan bases complain about the Leafs getting "all of the media coverage" but those same fans can't help but always compare their team situations to the Leafs. One thing you can't do though is compare the market in Calgary to that of Toronto. More than half the league are "small market" teams compared to Toronto and yet, people are saying Matthews is going to leave because he wants to go somewhere with more exposure and where he can have more of an impact. Where is there more exposure and a place to have a bigger impact than the biggest hockey market in the world?
According to the guys on OverDrive, Matthews was willing to take an 8-year deal back in 2019, but the Leafs were in a tight spot because of the John Tavares and Mitch Marner salaries having to be accounted for too. Host of Overdrive Bryan Hayes said, "You know Matthews is sitting in Arizona right now like 'here it comes' when he flies back up here in a month his first media day he is going to be peppered."
Of course, we don't know if the story is an exaggeration or where that information comes from, so I suppose we should take this information with a grain of salt, but if we're reading between the lines, maybe the fact that he was willing to go the full 8 the first time around, it means that re-signing with the Leafs is just a formality at this point. Maybe he's already a Leaf for life in his mind.
Dave Feschuk chimed in to add to what Hayes said with, "Don't think we're talking about this for two years though. Next summer when he's eligible to sign the extension they have to set a drop dead date. Either sign or hold an auction and highest bidder wins." Feschuk makes a valid point and it is the most logical idea that the Leafs will pursue. As much as the Leafs would likely be okay playing out the final year of Matthews' contract, they can't risk losing a generational goal scorer for absolutely nothing, and the return they would get for trading him would be ridiculous.
Another valid point that was made by Carlo Colaiacovo is that Matthews' future depends on what the leafs do next season. The Leafs need to get over the first round hump next year if they want to keep Matthews and if they don't, the chances of him resigning would likely drop considerably.
Hopefully we don't have to hear about this for two full seasons. If we do, it will be the media's fault Matthews leaves. No one wants to answer the same questions for two years, so everyone needs to relax and enjoy the next season or two of 60+ goals from a generational talent the Leafs have never had.