The Athletic dropped quite the article this week, breaking down the collapse of the Toronto Maple Leafs this season and outlining how involved MLSE CEO Keith Pelley got at this year’s NHL trade deadline. Apparently, he walked into the Maple Leafs’ trade-deadline war room armed with notes on potential returns that staff believed were generated by large language models and AI tools.
While Pelley has denied any suggestion that he was going to use AI to come up with and help run the hockey operations side of things, specifically trade proposals that did or didn’t happen that day, there is a lot of chatter about how the traditional hockey ops process in Toronto might be changing.
With that in mind, the idea of coming up with some mock/fun trade ideas that Pelley might have pitched or could pitch was too enticing to resist.
Imaginary Trade Ideas Pelley Could Have Pitched
Here are some fun, but potentially realistic, data-friendly trades an AI-optimized Pelley and his advisors might have brought to the table on deadline day. Or, perhaps these are ideas that will be explored this summer.
**Author’s Note: Full disclosure, some of the content below was generated by AI, simply because that’s the point of the exercise. My own non-AI comments are also attached.
Max Domi to a Contender for a 2026 2nd-Round Pick + B-level Prospect
Pelley might have seen that AI models view Max Domi’s $3.75 million cap hit (through 2027-28) as inefficient for a 31-year-old depth forward with inconsistent production. Moving him now, while he still has appeal as a playoff contributor, clears space and restocks a thin prospect pool.
My own AI dig suggested that a realistic return might include a mid-second and a young forward prospect.
** Author’s Note: Domi was named several times this past season in trade rumors. It doesn’t seem far-fetched to imagine he might be moved. While he’d got two seasons left, it’s always better to trade an expiring contract than to let it walk out the door. If they don’t see Domi as a fit long-term, get on it right away. Domi does have a 13-team no-trade list.
At 34 and on a $3.5 million deal (two years remaining), Oliver Ekman-Larsson has rebounded this season, offering the club strong veteran minutes. If Pelley punched the defenseman’s name into an AI tool, it would likely have shown solid trade value from contenders in need of defensive depth. It may also have suggested that retention would have upped the return.
My AI search spat back a return of a 2026 3rd-round pick + young D prospect.
** Author’s Note: We know that Ekman-Larsson’s name was out there at the deadline. It came as a bit of a surprise that he wasn’t traded. What would have been interesting to know is whether Pelley’s AI model recommended selling high. If asset management is part of what Pelley might be trying to accomplish, there is a good chance his value will never be greater than it was at this season’s deadline.
Trade One of the Goalies For a Top-6 Forward Prospect or Mid-Round Picks
Toronto has goaltending depth with Joseph Woll, Anthony Stolarz, and Dennis Hildeby. One has to imagine that Pelley’s AI tools told him to move one of them.
His AI probably suggested flipping one for scoring help or draft capital. Mine suggested a top-6 forward prospect or mid-round picks. Woll might fetch a mid-first- or young-winger; Stolarz, a second-plus prospect. It would have been difficult to assess Hildeby’s value.
** Author’s Note: A trade like this would have freed up $2.5-3.7 million on the Leafs salary cap and potentially helped them fill a hole on the roster somewhere. Three goalies vying for minutes rarely work. His AI would have told him that, too. One has to imagine that injuries and predictive time away would have factored into which goalie was best to trade. We don’t really believe the Leafs will start next season with all three on the roster, do we?
Matthews Knies For a Huge Haul
There was clearly talk about Matthew Knies at this season’s deadline. But what might an AI model have suggested as a viable return? Does Knies plus a pick to a contender get the Maple Leafs a young top-6 forward, first-round pick, and high-end prospect? Maybe.
Knies, 23, just delivered 23 goals, 43 assists, and 66 points in 79 games on a new six-year, $46.5 million extension ($7.75M AAV through 2030-31). Deadline reports indicated the Leafs were seeking premium packages (two firsts plus a prospect, or one first plus two high-end prospects).
** Author’s Note: We have to assume that an AI model might have flagged trading him at peak value as a potential mistake without a massive return. But it may also have thrown out the idea that Toronto could have nabbed a big package, which could explain the last-minute nature of his name coming up at all. A realistic haul from a team like Anaheim, Buffalo, or Chicago: a young NHL-ready scorer, a protected 2027 first, and a blue-chip prospect. Do the Leafs revisit that this summer?
