This will never happen but if I am Dubas I am giving it a shot.
If the Leafs do indeed find success this postseason, I bring the three of them in and try and sell 5 year deals to all of them at a minimal raise.
Matthews 5×12
Marner 5×11
Nylander 5×8
If playing together matters to them, and if the have made it to the finals, or won a cup then the sell is they would have 6 more years to win a few more together, knowing rhe cap will go up, Tavares' 11 million comes off the books and they can retool with more than just league minimum.
They would all be 30-32 and still be able to sign a 4-5 year deal at the end wherever they choose and for still pretty good money