As an elite player at a premium position and a pending UFA in his mid-20s, he can more or less write his own check. It’s clearly not a player or position a team can readily replace.
It has been reported that Matthews held firm on signing a shorter-term deal – which is obvious given he only signed for four years – even though the Leafs pushed for more. Realistically, the club never held any leverage to really push back, and trading Matthews away would have opened a whole can of worms. As Brad Treliving recently experienced with Calgary, when star players want out, even if talent is acquired in return, a team will feel the pain of losing a true star.