Objectively... a 5-6 year deal isn't the worst idea... it's worked pretty well for Rielly & Kadri.
Here's why:
- Let's say, that Matthews signs a 5 year deal, taking him to unrestricted free agency. He'll be a UFA at age 26, 6 years from now. Tavares, at $11m, would be a reasonable benchmark for how his negotiation would go, with obviously having 6 years worth of inflation. The deal that he signs, likely in the neighborhood of $16m / season.
If he signs an 8 year deal, those "last 3" years are worth about $48m. In signing an 8 year deal, we do of course have to look at McDavid, Eichel, etc. Personally, I think McDavid is a better player, and the Leafs will struggle if they sign Matthews to a contract that is the exact same as McDavid's for 7 out of 8 years of it. That being said, I can see Matthews demanding the exact same contract -- 8 years, $100m.
Dubas can agree to the concept of him being worth the same contract as McDavid; without having to agree to terms -- citing the fact that he wants to build a stronger team around him. IF you take the final $48m out of the deal, it becomes a 5 year, it becomes a $10.4m deal. That gives the Leafs an additional $2m worth of flexibility, to potentially win a cup in the next couple years. Yeah, there's a notion that you don't mess around with your star player contracts and you find somewhere else to save, but there's also the realization that nobody else has $2m worth of negotiating room.
This is exactly what Chicago did with Toews & Kane after their ELC deals.
Furthermore, from a practical perspective, consider this. It's 5 years down the road, the Leafs have won 2 cups with Matthews having earned just over $50m in the last 5 years. Does Matthews need to strike gold on a 7-8 year deal at $16m? or does he look at the situation and say "I'd like to continue winning, and I'll take $13 or $14m over the next 7-8 years to remain in Toronto and do so.