Breaking down every trade from Treliving’s tumultuous Maple Leafs tenure

The Treliving era in Toronto was a rollercoaster. 

There were the highs — an Atlantic Division title, a post-season that began with a brief glimmer of promise — and there were, of course, the lows. The Toronto Maple Leafs are still wading through them now, playing out the final two weeks of a dismal campaign that will end as the organization’s shortest in a decade.

The 56-year-old leaves the Maple Leafs an organization in crisis — set to miss the post-season for the first time in this core’s era, its future looking murky. Though, to be fair to him, Treliving inherited a team that was far from stable, too. When the former Calgary Flames exec arrived, Toronto was just coming off a dramatic off-season saga that saw Kyle Dubas ousted, the club thrown into a moment of disarray, and Treliving sought out to steady the ship.

For a spell there, it seemed he had — the 2024-25 Leafs rode stellar goaltending all the way to a top-five finish in the league’s standings, and a raucous series win over the rival Ottawa Senators. But they ultimately suffered the same fate as Dubas’s Leafs — bounced by Florida in the second round. Then Mitch Marner left, the goaltending magic dried up, and the whole thing came apart at the seams.

There’s plenty of blame to go around for the current state of the blue-and-white. The group’s core leaders and head coach Craig Berube certainly wear their fair share of it. But focus in on the impact Treliving had in the areas he could specifically affect, and it’s clear he wears it, too. His missteps on the trade market are a worthwhile starting point.

That in mind, on the heels of the organization parting ways with the manager earlier this week, let’s take a look back at every trade Treliving made during his time at the helm, and what his work on the market says of his tenure as Maple Leafs GM:

Oct. 8, 2023: Maple Leafs trade Sam Lafferty to Vancouver for 2024 fifth-round pick

The first move was an odd one. Lafferty was shipped to Vancouver not because the Maple Leafs had no use for him, but because of cap issues — the club had no room for his $1.15-million cap hit, opting to use that final piece of the cap puzzle to give young Fraser Minten a shot instead. It wasn’t a significant loss. Still, Lafferty was a useful depth option — quick and physical, just the type of bottom-six piece the club would find itself missing over the next few years.

Feb. 29, 2024: Maple Leafs bring back Ilya Lyubushkin in three-team deal (Toronto acquired prospect Kirill Slepets too, while Anaheim received Toronto’s 2025 third-round pick and Carolina received Toronto’s 2024 sixth-round pick)

The deal itself was fine — Toronto brought back a familiar face, with some salary retention, to plug a hole. But the context around it is more questionable. So light on right-handed defenders was the organization at the time, then-head coach Sheldon Keefe was forced to consider deploying Marner on the blue line after injuries took out his top options. Treliving set his sights on Chris Tanev but struck out, so the club turned back to Lyubushkin. He was solid enough, and filled a need at the time.

Mar. 7, 2024: Maple Leafs acquire Cade Webber from Carolina for 2026 sixth-round pick

A low-stakes swing. Coming out of Boston University, Webber — a six-foot-six, 220-pound blue-liner — has gone on to log two seasons for the AHL Marlies.

Mar. 7, 2024: Maple Leafs acquire Joel Edmundson from Washington for 2024 third-round pick, 2025 fifth-round pick

At the time, this seemed a worthwhile addition. Edmundson came in as a seasoned veteran with Stanley Cup pedigree and plenty of playoff experience. He added some needed size and bite to Toronto’s blue line. And while the 30-year-old was no longer at the level he’d found earlier in his career, the cost to bring him in wasn’t too steep. He was fine for the nine regular-season games and one post-season round he played in a Maple Leafs sweater, before he inked a four-year deal in L.A.

Mar. 8, 2024: Maple Leafs acquire Connor Dewar from Minnesota for 2024 fourth-round pick, Dmitry Ovchinnikov

Dewar arrived in Toronto with a reputation as a solid depth piece in Minnesota, joining at the deadline to bolster the Leafs’ bottom six. The bigger picture here makes this one look a bit questionable. Dewar didn’t find a fit in Toronto and, as we’ll see further down this list, was eventually shipped out of town. And yet he was a useful depth option before he got to Toronto, and after he left Toronto — he’s since become a quality bottom-six contributor in Pittsburgh this season, where he’s put up 14 goals and 30 points from the Penguins’ fourth line.

Jun. 23, 2024: Maple Leafs swap 2024 fifth-round picks with Chicago, and again with San Jose

Not much to see here, simply some low-stakes asset management.

Jun. 28, 2024: Maple Leafs trade 2024 first-round pick to Anaheim for Edmonton’s 2024 first-round pick, Boston’s 2024 second-round pick

The Maple Leafs used the first-rounder they acquired (No. 31) to draft Ben Danford. Anaheim used Toronto’s original first-rounder to draft Norwegian defender Stian Solberg.

Jun. 29, 2024: Maple Leafs acquire Chris Tanev’s rights for 2026 seventh-round pick, Max Ellis

While the deal Treliving ultimately signed Tanev to is another matter — particular the six-year term, which now looks questionable — acquiring the defender’s rights was a worthwhile move. The club had been desperate to bring in the rugged, right-handed blue-liner. And while injuries have caught up with Tanev, when he was in the Maple Leafs’ lineup the veteran had an undeniable impact, both in terms of his defensive prowess and as an emotional leader. Trading away a seventh-rounder and a prospect who wasn’t going to crack the big club’s roster any time soon seemed a worthy price for working out a deal with Tanev before he hit free agency.

Jun. 29, 2024: Maple Leafs trade 2024 second-round pick to Florida for 2024 second-round pick and 2024 seventh-round pick

Again, not much to see here. Toronto used these picks to draft winger Tinus Luc Koblar and defender Nathan Mayes.

Oct. 31, 2024: Maple Leafs trade Timothy Liljegren to San Jose for Matt Benning, 2024 third-round pick, 2026 sixth-round pick

A deal that made sense for all involved at the time. The 25-year-old flashed plenty of potential over the course of his six years in Toronto, but it never fully came together for Liljegren in a Maple Leafs sweater. In 2024-25, he found himself a healthy scratch for much of the campaign’s opening month, and sought a fresh start. Treliving found a decent return, and Liljegren found a new opportunity. The Sharks traded the blue-liner to Washington two years later.

Mar. 7, 2025: Maple Leafs acquire Reese Johnson from Minnesota for future considerations

Another fine, low-stakes swing. Johnson remains in the AHL with the Marlies.

Mar. 7, 2025: Maple Leafs acquire Brandon Carlo for Fraser Minten, 2026 first-round pick, 2025 fourth-round pick

This is where it all started to truly go sideways. And it’s a fair bet this deal will be remembered as the focal point of Treliving’s Maple Leafs tenure. The issue isn’t Carlo — the longtime Boston Bruins defenceman was seen as a positive addition for Toronto’s top four at the time, and while he and the entire Leafs blue line have struggled this season, Carlo was solid enough during that 2025 post-season. 

It’s the cost that stung Treliving’s blue-and-white legacy. First, there was the matter of Minten, one of the organization’s few prospects with any type of big-league promise — the 21-year-old centreman has 17 goals in his first full NHL campaign with Boston this season. Then there were the picks, specifically the first-rounder that came with only top-five protection, rather than the more common top-10. 

As the Leafs have plummeted down the standings over the latter half of the 2025-26 season, the fanbase has become consumed with tracking whether their club will fall far enough to keep their pick and draft in the top five, or — more likely — watch this disappointing season end with Toronto shipping a high first-rounder to the rival Bruins.

Mar. 7, 2025: Maple Leafs trade Connor Dewar and Conor Timmins to Pittsburgh for 2025 fifth-round pick
It pales in comparison to the deal above, but this one feels like another unnecessary misstep. While Dewar didn’t make much of an impact in Toronto, the rest of the forward’s career suggests he’s a useful bottom-six talent if deployed correctly. As mentioned earlier, he’s gone on to put up a career-best campaign for Kyle Dubas and the seemingly playoff-bound Penguins this season. Toronto traded away Dewar, and decent depth defender Timmins, to Pittsburgh essentially for free.

Mar. 7, 2025: Maple Leafs acquire Scott Laughton in five-piece deal (Toronto brought in Laughton, a 2025 fourth-round pick and a 2027 sixth-round pick, while Philadelphia received the Maple Leafs’ 2027 first-round pick and Nikita Grebenkin)

This was another key brick in the path that led to Treliving’s eventual exit. Again, context is key. With Toronto vying for a division title and gearing up for a post-season run, all eyes were on the front office to bring in some centre depth. Veteran Brayden Schenn was among the leading targets coveted by the fanbase. A deal was reportedly on the table, but the price was steep. In the end, Treliving pivoted to Laughton, but still wound up relinquishing a first-round pick. 

Laughton endeared himself to the Maple Leafs faithful and brought plenty of spirit to the club’s bottom six, but the veteran simply wasn’t the type of offensively gifted depth scorer Toronto needed. The pressure on him was immense, it didn’t work out, and the Maple Leafs wound up moving him a year later.

Jun. 30, 2025: Maple Leafs acquire Matias Maccelli for 2027 third-round pick

Once again, context is important here. This deal alone was just fine — a flyer on a depth winger who’d showed some promise. The issue wasn’t necessarily the addition itself, it was how Maccelli fit into the overall project of rebuilding the Maple Leafs’ offence as Marner prepared to move on from Toronto. 

A central misstep that sunk the Leafs this season was the front office falling short in using the cap space gained by Marner’s exit to bring in players who could replace No. 16’s offensive impact. Maccelli would’ve been a decent acquisition as a depth contributor, but he was instead slotted in as a top-line option alongside Auston Matthews and Matthew Knies, in a spot that was crucial to get right. It was a big swing that seemed unlikely to work out. As the final weeks of the season arrive, it’s fair to say it hasn’t. 

Jul. 1, 2025: Maple Leafs acquire Nicolas Roy from Vegas in Mitch Marner sign-and-trade

Treliving did well in acquiring some centre depth here, rather than losing Marner for nothing. Still, the fact that the situation got to this point at all seems another key bit of mismanagement. There was a calculated risk taken to keep Marner in the final year of his deal, with the hope of attaining some last-gasp playoff glory. Then came the ill-timed request for the winger to waive his no-trade clause mid-season for a potential Mikko Rantanen deal, expectedly denied. Ultimately, the Maple Leafs lost one of their most valuable assets — a 100-point, Selke-nominated, Olympic-calibre playmaker — while recouping only a depth pivot they traded away a year later.

Jul. 10, 2025: Maple Leafs trade Ryan Reaves to San Jose for Henry Thrun

A decent deal to bring in some blue-line depth, undoing a Treliving signing for the veteran Reaves, who never quite found a consistent role in the club’s bottom six.

Jul. 17, 2025: Maple Leafs acquire Dakota Joshua from Vancouver for 2028 fourth-round pick

Among the moves Treliving and Co. made in the wake of Marner’s exit, adding Joshua seemed a more understandable swing. He brought some size to the mix, and had showed his offensive potential in Vancouver. While injuries have hampered the former Canuck’s ability to fully find his footing in Toronto, Joshua wasn’t brought in with the expectation that he’d spark offensive creativity in the top six. He was simply asked to slot in as a capable middle-six depth scorer. He’s had his moments, and a healthier campaign could still see him become a useful contributor in blue and white.

Mar. 5, 2025: Maple Leafs trade Nicolas Roy to Colorado for 2027 first-round pick, 2026 fifth-round pick

The Roy deal signalled the Maple Leafs officially pulling the plug on 2025-26. After winning their division a year prior, Toronto trudged into this season’s deadline as reluctant sellers, trying to recoup what assets they could as a lost campaign wound to a close. Getting a first-round pick for Roy wound up the best of Treliving’s moves at this deadline, but it also highlighted once again the fumbling of the entire Marner saga.

Mar. 6, 2025: Maple Leafs trade Bobby McMann to Seattle for 2027 second-round pick, 2026 fourth-round pick

As was the case with a few other key moments of the Treliving era, timing got the better of the Leafs when it came to McMann’s exit. From the outside, Toronto’s fate seemed sealed long before the deadline arrived, and McMann — a 20-goal threat with size and pace — emerged as the club’s most promising trade chip. But Treliving held onto the belief that the club might turn it all around, climb back into the fight, and make something of the season. The timing seemed off, the deal was left too late, and Toronto wound up missing out on what was a good chance to land a first-round pick. McMann has since collected seven goals in nine games for Seattle.

Mar. 6, 2025: Maple Leafs trade Scott Laughton to Los Angeles for 2026 third-round pick

It was much the same for Laughton. While a disappointing season meant a hefty return for the depth pivot was unlikely, the Leafs still approached the deadline with a coveted asset in Laughton, a veteran centre and a heart-and-soul leader. But once again, Treliving and Co. seemed to wait too long, watched it all go sideways, and came away with only a third-rounder.

In all, Toronto walked away having given up a first-round pick and a prospect in Grebenkin for 63 games of Laughton and a collection of picks that won’t move the needle.

More from Sportsnet

‘They were buzzing’: Speedy Sharks remind of Maple Leafs’ fun past

Maple Leafs eliminated from playoff contention with loss to Sharks