Ideally, Treliving would want to secure a long-term deal with Matthews. However, a short-term contract could benefit both sides.
"A four or five-year term actually allows the Maple Leafs a better opportunity to reassess when the cap is in a place where the team can afford to revisit his deal.
Being first is always risky because you get hit the most while carving a path for others. But, if Matthews signs a four-year deal, others will follow suit. Sooner than later, his deal won't seem like an outlier. He won't be the highest-paid player for terribly long, he won't be the only one looking to use his leverage, and he'll effectively change the way contracts are negotiated by the league's elite. That's not a bad thing for Toronto."
If Matthews chooses a four-year contract, he will become a free agent again at the age of 29. By then, the salary cap should have increased significantly, and he would still have the opportunity to negotiate a long-term contract. Typically, superstar players command around 15% of the salary cap. So, with a higher cap, Matthews could potentially earn even more.