A ton of these signing are absolutely best case scenario if all the core are absolutely committed to winning a cup with Toronto.

Realistically speaking i dont think Nylander or Matthews take discounts anywhere near what you've suggested here.

If Nylander continues to be a 30 goal ppg player he would get offered a lot more than 7M, and he would be a fool to accept a long term deal that doesn't give him a raise. When factoring in the increased salary cap this is him taking a huge pay cut just in terms of his current contract. Who believes Nylander is going to take a paycut?

Matthews is going to get offered huge money from a team like LA if he gets anywhere near free agency. He is going to be 26 years old when he is eligible to sign a new deal as a UFA. What team with 14M million in cap space isn't going to offer him that kind of money.

I still think there is a good chance we hold onto Matthews and Nylander but there is no way they take contracts with low of an AAV.

Perhaps, maybe the Leafs offer Matthews 12 and Nylander 7 on one year deals until Tavares comes off the books (resign him for say 4-5 million) then get the big money long term deals? Same with Marner. They've been paid the big money already, and they'll continue to get paid in TO, I just think its more constructive to take less and build a winning team around them. That allows them to sign a guy like Toews, or add another big name forward or dman the following season. Dubas and co need to learn from the cap mistakes they've made

I don't why any Leaf realistic fan think it so important to keep the "core together".
Hope you're right about the cap being that high in two years but I can't see it.

I think Matthews, Marner, and Rielly are shoe in's to stay, maybe let Nylander go for another big name free agent?