Win-Now-Mode Maple Leafs Get Notably Better With Blockbuster O’Reilly Trade

We should’ve known – as soon as we posted an article about the Toronto Maple Leafs’ top five trade targets, the Leafs would actually go out and acquire someone off that list. In this case, our No. 2 target, veteran St. Louis Blues center Ryan O’Reilly, was one of two experienced players Toronto GM Kyle Dubas acquired in a three-team trade late Friday night. In exchange for O’Reilly and forward Noel Acciari, as well as prospect forward Josh Pillar, the Leafs sent their 2023 first-round pick, a third-rounder (by way of Ottawa) this summer, Toronto’s second-rounder in 2024, and, to the Minnesota Wild (who were part of the deal to retain 25 percent of O’Reilly’s contract), the Leafs sent a fourth-rounder in 2025.

At first glance, some Leafs fans could be forgiven to think Dubas surrendered too much for two NHLers who both will be unrestricted free agents this summer. But a less pessimistic view is that (a) the Leafs haven’t traded away all their first-rounders in the next three drafts; (b) they plucked a genuine difference-maker in O’Reilly (and kept him from going to a divisional or Eastern Conference rival), and a solid depth forward in Acciari; (c) Toronto didn’t give up anyone on their current NHL roster; and (d) they didn’t have to include promising prospects Nick Robertson and Matthew Knies. Those are all major wins for Dubas.

As it stands now, the Leafs can employ arguably the top three centers in the entire NHL, if they choose to make O’Reilly their third-line pivot. Leafs head coach Sheldon Keefe could also choose to bump O’Reilly onto Toronto’s second line, by either moving O’Reilly to the wing, or moving star forward John Tavares to the wing. The playoffs are all about having options and having depth, and with one move yesterday, the Leafs now have excellent depth up front.

As per CapFriendly.com, Toronto is projected to have approximately $3.6 million in cap space by the deadline, and we’re expecting Dubas to use just about every dollar in space to improve his depth, either on the back end with their defense corps, or on the bottom-six forward group. There’s even an outside chance the Leafs could add a backup goaltender such as San Jose’s James Reimer as an insurance policy in case Matt Murray can’t get or stay healthy before the playoffs arrive.

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However, even if this is all Dubas does on the trade front, he’s hit a home run with the O’Reilly deal. Today, Dubas has pushed players down the depth chart; veterans such as winger Calle Jarnkroc, Alex Kerfoot, David Kampf and others are competing for a spot on the third and fourth lines. Knies may also get his first taste of NHL action in the coming weeks, but now, there’s no pressure on him to produce tons of offense. He can be gradually worked into the Leafs’ lineup, and earn his minutes with above-average play.

There was never any question the Leafs were going to push in all their chips this season, and the only real question was which NHL veteran they’d be acquiring to give themselves a legitimate shot at a Stanley Cup. O’Reilly gives them that assurance. O’Reilly needs to stay healthy for Toronto to thrive in the post-season, but you could say that about any key player on any NHL team.

The truth is, on paper, this is the best Leafs team we’ve seen in years. There are no more excuses for Toronto to not fail in the first round, and embark on a deep playoff run. The Leafs were in win-now mode when the season began, and they’ve underscored that reality with this blockbuster move.