Just six weeks into the 2026-27 NHL season, it would be tough to attach a final grade to Toronto Maple Leafs general manager John Chayka's trades. That said, the early returns are worth looking at, and many of them are closer than you think.
John Chayka's multiple goaltender trades might have backfired
Looking back at Chayka's work, nobody turned over their roster to the degree that Chayka did this summer. Between the pipes, Chayka made a number of moves, which included sending Joseph Woll, and Dennis Hildeby out of the organization, while adding in key free agent acquisition, Sergei Bobrovsky..
Given the popularity of Woll and Hildeby, and an inherent fear of watching the departed have success elsewhere, both moves came with pushback from the Maple Leafs fanbase. No question, Leafs Nation loves to keep score. With that in mind, let's take a look at where these players went and how they are doing, and how the Leafs current goaltending tandem of Borovsky and Anthony Stolarz are working out.
When Chayka moved Woll and Hildeby, the fanbase pushed back immediately, citing good numbers from Woll in the 2025-26 season while predicting a bright future for Hildeby. Chayka moved Woll to the Philadelphia Flyers along with Benoit for Emil Andrae, Samuel Ersson and a 2026 third-round pick (85th overall).
Woll left Toronto having played 117 games, earning a 63-43-9 record, complemented by a .906 save percentage. He is currently sharing the crease with Dan Vladar in Philly, going 1-6-2 with a .899 save percentage and a 3.12 goals against average. To be fair, his goals saved above expected has been decent playing behind a struggling team.
Of course, we all know who took his spot on the Leafs roster: Sergei Bobrovsky. Fresh off Saturday night's 4-2 loss to Montreal, Bobrovsky sits with a 3-7-2 record, a bloated 3.34 GAA and an ugly .886 SV%. To say that his early performance has been disappointing would be an understatement, and with a three-year contract at $7 million a season, the signing is looking worse by the day.
Meanwhile, Anthony Stolarz has been excellent, earning a 5-1-0 record with a 2.66 GAA and .910 SV%. Interestingly, when Woll was traded, many fans questioned Chayka's decision, suggesting Woll should have stayed instead. Looking back (and I know it's early), Chayka looks to have made the right move, albeit tethered to the Bobrovsky signing.
Benoit has assumed third-pairing duty with the Flyers, playing in 13 games, with one goal and 18 penalty minutes to show for his effort while averaging 14:25 of ice time per contest. Simply put, Benoit is playing at the level he was playing at when he was with the Leafs: adequate, no surprises here.
Ersson was flipped to Ottawa for a 2027 fifth-rounder. Andrae was moved to the Columbus Blue Jackets in the Kirill Marchenko deal, so when you add it all up, the lasting return is that "highly coveted" 85th pick and some cap space. Verdict: I'd call it a wash, with Woll in tough behind a struggling team and Bobrovsky coming up small in Toronto thus far. The lone bright spot is Stolarz, so you have to give Chayka some credit for sticking with him.
How Dennis Hildeby is doing in Tampa
Which takes us to Dennis Hildeby. He was traded to the Tampa Bay Lightning along with a 2027 fourth-rounder and a 2028 third-rounder, with forward Nick Paul coming back to the Leafs. Through 16 games, the man they call "Hildebeast" has assembled a 3-0-1 record with a 2.95 GAA and a .880 SV%.
Taking Hildeby's spot is the man who booted him out of the crease during the Toronto Marlies' Calder Cup run last year, Artur Akhtyamov, who went 15-7 with a 2.22 GAA, .923 SV% and two shutouts during that stretch. Through seven games with the Marlies this season, he has a 2-3-3 record with a 2.97 GAA and .876 SV%. Simply put, he's not living up to expectations this year, but it's early in the season and there is hope that he will turn it around.
Paul has played a varied role with the Leafs, sitting on the third and second lines. Through 18 games, Paul has two goals and four assists for six points. Averaging 16:16 per contest, Paul has a minus-four rating and 17 shots on goal, is winning 44.9% of his faceoffs and has stepped up in the physical department.
Verdict: It should be noted that with Akhtyamov stepping up last season, Hildeby became the Leafs' fourth netminder. With a logjam between the pipes, Hildeby would have required waivers if he were to go back and forth between the Leafs and the Marlies, so trading him was likely the right thing to do. Add it all up and I'd say the Maple Leafs goaltending is no better or worse than last season, so we will call it a wash for now. That said, given his early season struggles, there is a real danger of Bobrovsky's contract not aging well. He will need a herculean effort over the next 66 games, with the hope that he can somehow find his way back to being at least an average netminder. In my mind, average goaltending (3.00 GAA and a .900 SV%) will be good enough most nights for the Leafs offense to win games. But if Bobrovsky continues to struggle, Chayka might regret his decisions.
Add us as a preferred source on Google