The bulk of the offseason narrative surrounding the Toronto Maple Leafs will be Auston Matthews’ future. That narrative won’t change until there’s a definitive answer. Whether Matthews stays or goes, the talk won’t change until the Leafs’ captain decides his future.
That said, part of the chatter will focus on what the organization can do to keep Matthews in Toronto. Much of that conversation will depend on the direction the Leafs are heading. The prevailing thought is that a rebuild would be a major red flag for the 28-year-old star.
But what if there was a way the Maple Leafs could rebuild and keep Matthews?
That possibility would almost entirely hinge on the 2026 NHL Draft Lottery.
Let’s assume for a minute the Leafs somehow manage to pull off a top-three pick. Such a situation could yield the Leafs one of the most sought-after prospects in this year’s draft. For instance, Gavin McKenna joining Toronto could be enough to entice Matthews to stay.
How about Keaton Verhoeff? Would a future number-one defenseman be enough to assuage Matthews’ desire to chase a Stanley Cup elsewhere?
These are possibilities that might delay a major decision this offseason. With the NHL Draft Lottery scheduled for May 5, a definitive call on Matthews staying or leaving could come after then.
Top draft pick could be massive selling point
Let’s assume for a minute that the Maple Leafs do manage to land a top-three pick in the 2026 NHL Draft. Such a situation could become a major selling point for the Leafs. The organization can convince Matthews that a high-end, generational prospect, like he once was, could be an accelerator towards a return to contention.
The opposite could also happen. The Leafs could fail to land their pick in the top five, ceding it to the Boston Bruins. In that case, it would be a hard sell to Matthews’ camp that the club is on the fast track to return to contention.
This entire premise is based, however, on the fact that Matthews desperately wants to win a Stanley Cup and is willing to leave Toronto to do it. The consensus is that he wants a Cup, but in Toronto.
That’s why keeping Matthews would be an extremely hard sell unless there was a tangible path forward.
GM Brad Treliving will have one of the hardest tasks in his career this offseason. He’ll need to build a convincing retool plan while finding a way to convince the team’s top star to stay.
It’s a fine needle to thread. If the organization can pull it off this summer, the feat may go down as the first step towards a championship.