The Toronto Maple Leafs have put in their best effort to remake their roster this current offseason. Led by new GM John Chayka, the Maple Leafs have pulled off various trades and free agent signings with hopes that they will all pay dividends for the organization as soon as this upcoming season.
However, in order to fit in all of the new additions, the Leafs were forced to say goodbye to numerous members from their 2025-26 roster as a result. For some, Toronto would likely have no problems foregoing, but for some others, they could potentially come back to haunt the club down the road. Here, we will take a look at 3 now former Maple Leafs players that Toronto will regret letting go this offseason.
3 players the Maple Leafs will regret letting go this offseason
F Nick Robertson
After putting forth a sensational juniors campaign in 2019-20 in which Nick Robertson compiled a whopping 55 goals and 86 points in just 46 games played with the OHL Peterborough Petes, many Leafs fans developed high hopes for the potential prolific scorer. However, whether it be injuries or inconsistencies, it ended up taking some time before Robertson finally saw regular time in the NHL. Nevertheless, just this past season, the 24-year-old winger managed to put up his best numbers of his professional hockey career with 16 goals and 16 assists for 32 points despite playing for the struggling Maple Leafs squad.
But with Toronto’s focus on adding key role players to their bottom six this offseason, along with having no spots open in their top six, it ultimately forced Robertson out of a role for the upcoming 2026-27 season. As a result, he was dealt to the Pittsburgh Penguins to reunite with his old boss Kyle Dubas where he will now have his shot to play alongside with the likes of legends Sidney Crosby and Evgeni Malkin. Robertson was never really given a long look to play in the Leafs top six during his time in Toronto. However, he will now have all the opportunity to crack the Penguins top six to maximize his scoring potential and could finally have the breakthrough campaign that many have been waiting for.
G Joseph Woll
With the Maple Leafs intention to sign goaltender Sergei Bobrovsky this summer, we all knew at least one of their regular goaltenders would be on the move to accommodate for the incoming star. However, it might have ended up being the one that Leafs fans were least expecting. Toronto opened up a spot by trading Joseph Woll along with defenseman Simon Benoit to the Philadelphia Flyers in exchange for goaltender Samuel Ersson, defenseman Emil Andrae and a 2026 third round pick.
Both Woll and Anthony Stolarz struggled in the Leafs net throughout the 2025-26 campaign. But it would have made more sense to move the latter rather than the former. First of all, both goalies have shown to be injury-prone during the past two seasons, with both spending significant amounts of time on the IR. Nevertheless, Woll (81 games) still ended up seeing more action with the Leafs than Stolarz (60 games) over that time frame. In addition, Stolarz is already on the wrong side of 30 at 32 compared to Woll at just 28 with still time to round into prime form, with the former also having a slightly higher cap hit per season ($3.75 million vs. $3.667 million).
As a result, Woll would have formed the more ideal reliable tandem with Bobrovsky going forward for the Leafs. But instead, Toronto will now have to hope for a huge bounce back year from Stolarz while praying that his health holds up even more at the same time.
G Dennis Hildeby
Finally, the one that could really come back to bite the Maple Leafs is the trade of young goaltender Dennis Hildeby along with two drafts picks to the Tampa Bay Lightning for rugged forward Nick Paul. The only reason why the Leafs moved the young 24-year-old rising prospect was because he isn’t waiver exempt entering the 2026-27 NHL season. Therefore, rather than risk losing Hildeby on waivers or potentially carrying three goaltenders into the start of the regular season, Toronto chose to recklessly recoup an asset instead.
Recall during the Leafs’ disastrous 2025-26 campaign, it was Hildeby that actually put up the best numbers among all of the Toronto goalies despite having a porous defense in front of him. The 24-year-old prospect amassed a solid 2.80 GAA and stellar .914 save percentage included registering his first career NHL shutout in 20 games of action with the Maple Leafs. So think of how much better those numbers could even be if Toronto managed to play at least some respectable defense last season. In addition, the Leafs don’t have a good history in giving up on young goaltenders so early, i.e. Tuukka Rask. Could this become Rask 2.0 as our EIL writer Jeremy Franks previously suggested? Only time will tell.
But with Artur Akhtyamov now being the only Leafs goalie prospect left that may or may not be NHL-ready yet, the Maple Leafs goaltender depth just got that much thinner with two young solid options gone in the same offseason.
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