According to NHL insider Elliotte Friedman, John Chayka and the Toronto Maple Leafs are going for it over the next two years.

The Maple Leafs only have captain Auston Matthew under contract for two more seasons, and it just so happens they do not have their next two first-round picks as the Boston Bruins and Philadelphia Flyers control the Maple Leafs’ firsts in 2027 and 2028.

That’s why Friedman believes that Chayka is doing everything he can to win now, meaning the team is not rebuilding despite missing the playoffs this past season.

Elliotte Friedman Says Maple Leafs Are Going for It

Speaking on the “32 Thoughts Podcast,” Friedman said that the Maple Leafs are doing everything they can to win the Stanley Cup over the next two seasons.

“My theory about the Maple Leafs is this. I think they’ve decided, especially since they don’t have their next two first rounders — Boston and Philly have them — they have Colorado’s 2027, but who knows when that’s to be. I think between that and Matthews having only two years left, they are on a train heading towards, like, steamrolling down the track. They’re like, ‘We’re going for this the next two years, as much as we can. We’re not handing a high first-round pick to the Bruins and/or the Flyers. We’re just not doing that, and if we have any chance of keeping Matthews, we can’t rebuild,'” Friedman said.

“So I think they’re going over the cliff, and they’re either going to hurdle over it like the bus in ‘Speed’ and land on all four wheels on the other side, or it’s going to work. Because I think they feel like if this doesn’t work and they lose Matthews, they’re probably going to have to rebuild anyway, right?”

Maple Leafs Picking No. 1 in Friday’s NHL Entry Draft.

The 2026 NHL Entry Draft takes place on Friday night, and the Maple Leafs have the No. 1 overall pick, which they are likely going to use to select Penn State U winger Gavin McKenna.

The team is also said to be considering other trades to land another top-10 pick to pair up McKenna with another young player on a similar timeline, with stud winger Matthew Knies reportedly being dangled about in trade talks. But to this point, the Maple Leafs have not accepted any trades from other clubs as the team has put a high price on Knies.

As Friedman noted, the Maple Leafs only have two more years left on Matthews’ deal to convince him to sign a long-term contract and potentially finish his NHL career in Toronto. If they are a winning franchise, it makes it more likely that Matthews will stay.

We will see what moves Chayka has up his sleeve in the coming week, with the draft and free agency both fast approaching, but it does appear that the Maple Leafs are trying to win the Stanley Cup within the next two years. After acquiring defenseman Darren Raddysh, look for the team to make some other big moves in an effort to win now.