It’s shaping up to be the most important trade deadline for the Toronto Maple Leafs, so we’re revisiting the past for any lessons that Brad Treliving and his staff can adhere to ahead of Friday.
The future does not matter for contending teams, going all-in is worth it
Considering the finite limits of the salary cap, there’s a natural inclination to be worried about draft capital, but not all trades are created equal and the future doesn’t matter for a win-now team like the Maple Leafs, who need some playoff success to appease a frothing fan base. Toronto traded its 2023 first-round pick, a 2024 first-round pick, a 2025 fourth-round pick, along with depth players Mikhail Abramov and Adam Gaudette in a package to receive Ryan O’Reilly. Going all-in is always worth it, the Leafs aren’t regretting their relative lack of draft capital and O’Reilly helped the Leafs advance to the second round of the playoffs.
It didn’t end the way both parties wanted, as O’Reilly left in free agency, but he formed a potent Ontario line alongside John Tavares and Mitch Marner, he boasted the Conn Smythe Trophy-winning pedigree the Maple Leafs, and every other team for that matter, would prioritize any given year, with some sound defensive responsibility. Toronto was in the habit of picking up former captains (Nick Foligno, Mark Giordano) to bolster its leadership group and O’Reilly fit the bill.
Luke Schenn was also acquired for a 2023 third-round pick, which was more than reasonable, given that he played sound top-four minutes throughout the playoffs. Jake McCabe and Sam Lafferty and two conditional picks were added in exchange for Toronto’s 2025 first-round pick, a 2026 second-round pick, Joey Anderson and Pavel Gogolev, while the Blackhawks retained 50 percent of McCabe’s salary. It’s a trade the Maple Leafs would make again without hesitating.
Some would easily point out that the Maple Leafs never advanced past the second round with O’Reilly, McCabe and Schenn on board, and the opportunity cost was a lot for a player that amounted to a rental. The alternative would see the Leafs in the exact same place, without taking a real shot at the Cup, and that’s simply untenable at this stage of the Auston Matthews-Mitch Marner era. The future does not matter, and it’s something Kyle Dubas keenly understand in his last hurrah. Brad Treliving should be doing everything in his power to go over the top this week.
Find a trade partner to retain salary before other contenders swoop in
It may be easier said than done to find a trade partner for a lucrative deal, but the Maple Leafs wisely took advantage of the Blues and Wild’s willingness to retain salary in the O’Reilly trade, and the Blackhawks in the McCabe deal. Teams can only carry three salary retention spots, and the Maple Leafs gamely capitalized on some flux within the Central Division.
It will take some salary retention in order for the Maple Leafs to land a target like Brayden Schenn, where the Blues have reportedly set an exorbitant price for their captain. Blues defenceman Colton Parayko may prove to be too costly, as well. Treliving will need to work the phones and his pre-existing relationships with other NHL general managers to find a seller that is willing to play ball, and get a key asset (Toronto ought to be willing to trade its 2026 first-round pick along with top prospects Easton Cowan or Fraser Minten, if needed) in return. The trade deadline isn’t always a zero-sum exercise, but the Maple Leafs will need some help from their friends.
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