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.

We’ve gone through what the Leafs can learn from the 2022 and 2023 NHL Trade deadlines this week, so we’ll take a look back to last year, the first season under Treliving’s supervision.

Taking this avenue won’t make the splash Leafs fans are looking for, but trading mid-round picks are a clear way of upgrading the roster with depth pieces, and it seems to be the route that Treliving prefers.

Toronto acquired Connor Dewar in exchange for Dmitry Ovchinnikov and a 2026 fourth-round pick, a day after adding Joel Edmundson for the New York Islanders’ 2024 third-round pick and the Chicago Blackhawks’ 2025 fifth-round pick. Cade Webber was also acquired at the deadline for a 2026 sixth-round pick. Treliving’s first move was to bring back Ilya Lyubushkin for a second Maple Leafs stint in exchange for a 2024 sixth-round pick and a 2025 third-round pick. And it largely served the goals of a Maple Leafs’ team that was, and is, still in their contention window.

Lyubushkin provided Morgan Rielly with some relief, while Joel Edmundson provided mixed returns for a Maple Leafs team that often defended well against the Boston Bruins but simply couldn’t score when it needed to. If a handful of mid-round picks are the acquisition costs for third-pairing defencemen, Treliving should unload the rest of his arsenal. It may not be a fun time to be part of the Maple Leafs’ scouting staff, who work tirelessly to prepare for the draft, but sellers can replenish their draft capital, while Toronto operates with a myopic, laser-like focus for the upcoming playoffs.

This is an extrapolation from the Leafs’ relative inactivity at last year’s deadline, and perhaps runs against Treliving’s philosophy: reward a contending Leafs by trading a prized prospect for an immediate upgrade. Easton Cowan’s meteoric rise from a reach at No. 28, to one of the most productive players from the 2023 NHL Draft class was an unforeseen development, and while Cowan could contend for a roster spot next season, he should be on the table in any deal involving a third-line centre. Fraser Minten is already pro-ready, or close to providing a facsimile of what his game will look at the NHL level, and he may be involved in discussions throughout the week.

The lone untouchable, aside from the Core Four forwards, and goaltending tandem, is Matthew Knies, who has provided surplus value as a first-line talent at age 22. Knies is a restricted free agent that will almost certainly re-sign with the Maple Leafs this summer, and he’s the only player on the roster that is essential to a real pursuit of the Stanley Cup, while also being an essential part of the team’s future. Toronto is in Year 9 of the Auston Matthews-Mitch Marner era, and the team routinely underperforms in the playoffs, but it has adhered to a new style of play under Craig Berube, making pragmatic, winning plays at the expense of a flashier game.

Remaining agile may seem like a necessity under the salary cap, but the best teams know when to maximize their windows, so Cowan, Fraser Minten, Ben Danford and Toronto’s future picks should all be up for discussion if it returns a meaningful upgrade.