What NHL Draft Lottery win means for the Leafs: four possible paths forward

May 6, 2026, 11:30 EDTUpdated: May 6, 2026, 11:56 EDT

Gavin McKenna, Auston Matthews, William Nylander and Matthew Knies

Can any other NHL franchise stir up this much scorn, hate, excitement and envy in a single 31-hour period?

On Monday afternoon, MLSE president Keith Pelley was sweating through acid-tongued questions on whether the man sitting to his right, new Leafs GM John Chayka, was a con artist. By Tuesday night, the Leafs were stumbling into the first overall pick, winning the NHL Draft Lottery with the fifth-best odds and launching a new era.

No matter how anyone feels about Chayka and his new tandem partner, executive senior advisor Mats Sundin, they’ve been dealt pocket aces on their first hand.

“Well, you need some luck, and we got it tonight,” Chayka told reporters, including The Leafs Nation’s Arun Srinivasan, on a Zoom call Tuesday evening. “A long road ahead, of course, lots of work to do still, but when you get a first overall pick, it’s a monumental type of opportunity and it’s a really good draft and a lot of good players.”

Though Chayka indicated he (understandably) has sat in on no scouting meetings yet and thus wouldn’t commit to Gavin McKenna as the No. 1 overall pick, it’s highly likely. He’s a dynamic scoring machine with an extremely high ceiling, a player who made major junior look easy and went to the NCAA as a 17-year-old in search of a challenge this past season. Daily Faceoff prospect analyst Steven Ellis offers a detailed breakdown of McKenna’s game here. Even if the Leafs were to pivot from him: Ivar Stenberg represents an elite secondary option, a well-rounded center with the ability to play huge minutes in all situations and drive the play at both ends of the ice.

The primary takeaway: the Leafs are guaranteed a franchise-changing player thanks to the enormous horseshoe jammed you-know-where.

The Draft Lottery win is a blast of fresh air for a franchise that needed it on so many levels. The excitement over picking first will serve as a merciful distraction from all the bad press swirling around the Chayka and Sundin hires. It also could drastically change what were going to be difficult conversations with captain Auston Matthews, who reportedly isn’t sure whether he’ll be back with the team for next season. The pick revamps Toronto’s prospect pool and opens up many new ways for Chayka to improve the roster, whether that means moving out veterans or deeming other lesser prospects expendable.

So what happens now? If we paint Toronto’s future with broad strokes at this early juncture of its offseason, I see four potential paths Chayka can walk, representing four very different approaches to making over a broken team.

THE RUN-IT-BACK OPTION: Keep core together, use McKenna as a Marner replacement

Losing Mitch Marner to the Vegas Golden Knights destroyed Toronto’s team chemistry and lowered the team’s skill bar irreparably this season. McKenna, clearly talented enough to jump to the NHL at 18 next season, has some similarities to Marner. McKenna, also a right winger, is a playmaker more than a shooter, blessed with truly special puck skills and vision – and actually has greater upside than Marner as a goal scorer. McKenna doesn’t have Marner’s defensive chops – the closer player comp for McKenna is thus probably Nikita Kucherov – but if we squint, we can see McKenna sliding in to fill Marner’s former role as a high-end facilitator at 5-on-5 and power-play weapon.

Having McKenna in the lineup could open up better looks for Matthews coming off the most disappointing season of his career and allow William Nylander to continue functioning as the primary threat on his own line at right wing. With John Tavares still playing at a high level relative to his age and bargain AAV, Matthew Knies mostly meeting the standard of scoring-line power forward and Easton Cowan developing on schedule, the Leafs’ top six would trend back up in the medium term. That would allow Chayka to use his $22 million-plus in cap space for addressing other areas of need, specifically the D-corps, which desperately needs one if not two pure puck-moving defensemen, a roster hole Chayka acknowledged in a scrum after the presser Monday. We also have to remember that Toronto doesn’t have its 2027 or 2028 first-round pick (it does have Colorado’s top-10 protected 2027 first-rounder), so that’s potential motivation to throttle back up with the current group.

Still, this path feels the stalest: even with Marner, the Leafs weren’t good enough to escape Round 2 in nine seasons. They probably need a more dramatic change than recreating him in an otherwise subpar lineup, don’t they?

THE RETOOL OPTION: Draft McKenna, trade another core winger for a defenseman

If the Leafs prefer to balance out their roster and devote significantly more resources toward their D-corps…they could treat McKenna as a long-term replacement for Nylander, who is still playing at a high level but reaching the end of his prime at 30, or Knies, who has reportedly generated a lot of interest on the trade market due to his unicorn skill set. Trading Knies, 23 and about to start a new six-year contract extension, would feel counterintuitive to a new-wave mindset. But might the Leafs explore trading Nylander? What if that means, for instance, a deal that brings someone like Adam Fox to Toronto? He’s one example of a potentially available defenseman who would fit Toronto’s team need. In a perfect world, however, the Leafs would probably rather use their cap space rather than a still-vital veteran scorer to bring in help. A Nylander trade also would put a lot of pressure on McKenna to be very good very quickly.

THE START-OVER OPTION: Trade Auston Matthews, build a new team around McKenna

Matthews, 28, is already humming and hawing over whether he wants to re-sign after two years. His value has arguably never been lower coming off an injury-shortened season, but it’s offset by the fact he’s still in his late prime years. He’d command a significant trade return, with the package the Vancouver Canucks got for Quinn Hughes the likely starting point for the decade’s most prolific goal scorer. Imagine, for instance, hitting the San Jose Sharks up for the No. 2 pick in this draft plus another piece from their stacked prosect pool? How about the Utah Mammoth for a deal built around Tij Iginla? It would set Toronto back in the short term but would end the Matthews/Marner era and kickstart a new generation and team identity. If you subscribe to the notion the Leafs need to clean out all the rot, Chayka could consider something drastic like this. It would take some serious gumption to trade the franchise’s all-time leading goal scorer at the start of your GM tenure but, if Matthews wants out, he’d give Chayka no choice anyway.

THE ALL-IN OPTION: Trade the first overall pick

If Chayka wants to drink all the Brad Treliving juice and nudge the franchise even closer to the edge of the cliff, trading the pick represents that big red button to push. In doing so, the Leafs could target another franchise seeking major change in hopes of inviting an overpay. Example: sending the pick to the New York Rangers for a package involving Fox and Alexis Lafreniere, or approaching the St. Louis Blues for something centered on Robert Thomas. Dealing the No. 1 overall selection is the riskiest option available, even riskier than a Matthews trade, because an incorrect bet would mean a missed opportunity at starting over and a franchise that could bottom out again when Matthews’ contract ends. This idea certainly isn’t the recommended one; I’m merely presenting all the potential paths to walk.

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POST SPONSORED BY bet365

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