The No. 1 pick in the 2016 NHL Draft, Matthews has 132 points (74 goals, 58 assists) in 144 games during his first two NHL seasons. He is entering the final season of his three-year, entry-level contract and can become a restricted free agent after the season. He became eligible to sign a contract extension July 1.
Matthews left CAA, which represents Tavares, for Orr Hockey Group in June. Orr's group also represents Edmonton Oilers center Connor McDavid, the No. 1 pick in the 2015 NHL Draft who signed an eight-year, $100 million extension July 5, 2017, prior to his third NHL season.
"I don't think it's about the money," Orr said. "The kid is going to be a heck of a player. It's like John Tavares in free agency. It's nothing about money. It's where he wanted to play. He wants to play in Toronto.
"If [an extension] doesn't happen this year before the season starts, he still has a year left, and he'll fulfill his contract and we'll see what happens after that. Hopefully they will get it done. He likes Toronto and he wants to stay in Toronto. I'm sure they'll get it done."
Whatever happens, the negotiations will not become a public spectacle, Orr said.
"You're not going to read much about it," he said. "Our guys will be trying to get it done and hopefully we will. But you're not going to be reading something about it every day. You can guess all you want. When it happens, it will be announced. We're not having a big thing about it.
"The job is to get the job done, make the Leafs happy, make Auston happy and let's go. That is what it is about."