The Toronto Maple Leafs are now almost two full weeks since Auston Matthews was eligible to sign an extension and the two sides have yet to settle on a contract.
The goal should always for the Toronto Maple Leafs to find a way to extend Matthews and not have to go down the trade route.
I believe that you ask Matthews how long he wants and for how much, you then put pen to paper. However, if the two sides enter August and have not yet settled on a contract, GM Brad Treliving has to explore trading their top player.