It is quite rare for an NHL team to get all their homework done on the very first day of free agency. But that was what exactly happened for GM John Chayka and the Toronto Maple Leafs once the floodgates opened. The Maple Leafs would literally use up all of their cap space to add multiple key pieces to round out their roster ahead of the 2026-27 NHL season. Talk about an offseason overhaul, the Leafs were definitely not kidding around.
So how well did Toronto do with all of their bold moves so early? Here, we will grade the notable transactions that took place for the Maple Leafs so far in free agency.
Colton Sissons to a two-year, $8.5 million deal
Toronto added some much-needed toughness to their lineup who could also play center with the addition of 32-year-old veteran Colton Sissons. However, projected to play on the fourth line for the Leafs while not likely to average more than 10 goals or 25 points per season, a $4.25 million AAV salary appears to be a bit steep and could end up hurting the Maple Leafs a bit more than Sissons hurting his opponents.
Grade: C-
Teddy Blueger to a two-year, $5 million deal
Teddy Blueger brings his gritty, physical style of play to the Leafs in a potential checking role for 31-year-old forward. As a defensive, penalty-kill specialist as well, Blueger can provide some secondary scoring while adding close to 20 points per season. More importantly, he was also a part of the Stanley Cup winning Vegas Golden Knights team in 2022-23, getting valuable championship experience.
Grade: B+
Brandon Duhaime to a three-year, $7.8 million deal
Similar to Blueger, Brandon Duhaime enjoys a physical game where he can lay hits on his opponents to wear them down. Most fit in a checking role, Duhaime is also effective as a penalty killer and in defensive situations. But in terms of offensive output, don’t expect a lot from the 29-year-old winger, as anything in the double-digit range for points would already be a huge season. As a result, with a similar salary AAV as Blueger, it makes Blueger worth it just a bit more.
Grade: B
Jack Roslovic to a two-year, $8 million deal
Toronto actually coveted Jack Roslovic last offseason, but things didn’t end up working out. Well, the Leafs finally got their man this time around at $4 million AAV per season. As the good friend and former teammate of Auston Matthews back in the US National Team Development Program, Roslovic could put that built-up chemistry to good use with the Maple Leafs. Coming off back-to-back 20+ goal campaigns, don’t be surprised if he ends up among the top two scoring lines with Toronto, with a potential breakout season in store.
Grade: A-
Trade for Nick Paul from the Tampa Bay Lightning
This move wasn’t more a signing but rather a trade taking place during free agency. With former Leafs goalie Dennis Hildeby needing to clear waivers to be sent to the Marlies for the upcoming season, Toronto didn’t want to risk to lose him for nothing. As a result, Chayka turned Hildeby and a couple of draft picks (2027 fourth-rounder, 2028 third-rounder) into their potential 3C solution in Nick Paul. Despite a down season in 2025-26, Paul has shown previously that he can contribute 20+ goals and 40+ points per year while playing responsibly in his own end. With the opportunity to play for his hometown now, look for the 31-year-old veteran to regain his form in front of the home crowd.
Grade: A
Trade Nick Robertson to the Pittsburgh Penguins
With the huge influx of role players, it essentially left Nick Robertson without much of a role with the Leafs next season. As a result, Toronto made sure they could get an asset in return for the once-promising scoring forward by securing a 2028 fourth-round pick from the Pittsburgh Penguins. So Robertson now gets his shot to play with Sidney Crosby and the Leafs get some draft capital replenishment for 2028.
Grade: B
Sergei Bobrovsky to a three-year, $21 million deal
Perhaps the biggest transaction by the Maple Leafs this offseason, Toronto finally has a star, potential game-changing goaltender in Sergei Bobrovsky. Sure, Bobrovsky is coming off his worst season of his career with the Florida Panthers where he posted a 3.07 GAA and .877 save percentage to rank him among the worst in the league. However, he did have a banged up, struggling squad that played in front of him all last year. The Maple Leafs are sure hoping he will be Eddie Belfour 2.0 where he would come in and provide the elite goaltending that they need to lead Toronto back to the playoffs despite closing in on 40 years of age. If Bobrovsky succeeds in doing that, A+ should be the grade. But if he bombs out and proves that 2025-26 was actually a reality, then he deserves no more than a D. Averaging it out leaves it at a B-.
Grade: B-
To round things off, the Maple Leafs also made some depth signings with Zack MacEwen, Cole McWard and Henrik Rybinski. But they will likely need to really impress to usurp any regular from the Leafs lineup. With a total of nine new players added to the organization in just two days, let’s just say Toronto will certainly have a different look when the 2026-27 NHL season rolls around. Nevertheless, it was quite the accomplishment to do all that so much so quickly for the new Leafs GM. Only time will tell now whether they all end up working out. But for now, the Leafs and their fans should feel excited once again.
Overall Grade: B+
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