It might just be me but I wouldn't make either trade. I think marner is better then pasta but the other trade is tough.

Id rather keep Matthews and Marner.

They wouldn't trade Matthews and Marner

I think both Leafs, Avs, and Bruins all say no. MacKinnon at 6.3m for 4 more years....Ill take that over Matthews who probably is going to be 12m for 6 years.

The single reason why the Leafs would want this, is if the price for Matthews and Marner went up significantly relative to signing earlier

The guaranteed condition by teams trading for them would be to negotiate an extension in advance

Once the uncertainty is off the table, there isn't any room for one side to win the trade over another. The deal doesn't happen because it would ruin the chemistry of a good thing in each of the teams listed.
You make 2 player trades when the chemistry is bad, or they fill different roles.

If Nylander ends up traded over the summer, it's partly cap considerations. In that case, you'll see a lower cap hit coming back -- which means multiple prospects + picks.
Probably would have been smarter to do that before last year's draft which was strong, instead of at this year's draft which will be weak.

Hopefully the organization is taking the money from my phone bill hike and learning to invest that in a better plan for the future of the Leafs.