Brad Treliving's First Deadline as Toronto Maple Leafs GM Was a Flop

2023 Upper Deck NHL Draft - Round One
2023 Upper Deck NHL Draft - Round One / Bruce Bennett/GettyImages
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Connor Dewar

Treliving finished his first deadline as Leafs GM by trading prospect Dmitry Ovchinnikov and a 2025 fourth round pick to the Minnesota Wild for forward Connor Dewar.

There was no retention on Dewar as he only makes $800,000 and is an RFA at the end of this season with arbitration rights.

Dewar is primarily a fourth line leftwing/center who possesses above average defensive abilities given his usage.

He will be 25 by the time his deal is up and although he has mainly been a fourth line player thus far, with his speed, forechecking ability, and his production this season, there are indications he could play slightly higher up in the lineup.

I would not get my hopes up though, as he will likely stay as a fourth line/extra forward but could move up to a third line role if need be.


Overall, the Toronto Maple Leafs entered the deadline period with clear needs and did not seem to really address those needs in any meaningful way.

They needed extra forward support, likely in the way of a middle-six center but were unable to pull the trigger. Even acquiring extra offensive support in a middle-six winger would have been suffice. They did address a weakness however, by acquiring Dewar who should help the team’s overall defensive abilities upfront.

They also needed help on defense, mainly a top-four right-handed defenseman at least but acquired Edmundson, a lefty, and Lyubushkin who do not really fit that mould. So far, the Rielly-Lyubushkin pairing has worked but as I said before, it did last time until it was exposed in the playoffs. 

The Leafs held onto their first round pick and their main prospects but did part with many picks over the next three drafts and prospect Dmitry Ovchinnikov. (All Stats Via

In total, the Leafs traded a 2024 and 2025 third rounder, a 2026 fourth, 2025 fifth, and a 2024 and 2026 sixth. That is a lot of picks to trade and to not address any of the two most prominent needs. This is especially the case when Adam Henrique, Alex Wennberg, and Jack Roslovic all went for relatively cheap and could have fit one of those needs. 

In the most optimistic sense, these are underwhelming acquisitions. It remains to be seen whether these moves work or not but they do not inspire a lot of confidence.


The Leafs undoubtedly are a heavier and tougher team today than they were two weeks ago and some say that will work in the playoffs but if history has shown us anything, they could leave the Maple Leafs much more exposed to the opposition’s attack come playoff time.