Maple Leafs’ Chayka Makes His Mark on First Day of Free Agency

Days after Toronto Maple Leafs general manager John Chayka aced the 2026 NHL Draft, he immediately shifted his focus to the official start of the season with the Free Agent Frenzy. On July 1^st, he was open for business and he made it a point to rebuild the team and make them playoff ready once again. 

Chayka definitely sought out and made his mark; improving the Maple Leafs’ bottom-six and secondary scoring. More importantly goaltending, as he signed two-time, Stanley Cup Champion Sergei Bobrovsky to a three-year, $21 million deal. While he was the big name target off the board, Chayka didn’t stop there as he continued to change the makeup of this team. Here’s a recap and analysis of his moves on the first day of free agency. 

Good Bet on Bobrovsky With Contract

Coming into free agency, many wondered what a Bobrovsky contract would look like. He was reportedly asking for $6-7 million and a long-term deal. With his seven-year, $70 million contract with the Florida Panthers ending, the 37-year-old goalie wasn’t going to attract many suitors as he’s an aging goaltender and teams are smart enough to not make that long of an investment. 

Bobrovsky has a track record of success and his resume speaks for itself, but there’s still risk signing a goalie this late into their career. His numbers last season weren’t that great and that’s why many were hesitant on signing him. He posted an .877 save percentage and a goals against average of 3.07. Among goalies to have played 1,000 minutes last season, he had a goals saved above average of -17.07. The Panthers dealt with injuries, but Bobrovsky’s results aren’t eye popping and give some doubt for a rebound.

With Chayka giving him a shorter-term deal and a reasonable, albeit risky cap hit for his age, it was the best case-scenario. It’s a gamble for the Maple Leafs, but they get a legititmate starter. It’s also a good bet on Bobrovsky as he has an opportunity to bounce back and show that last season was a one off. If it was anything more than three years and more than his current cap-hit, it wouldn’t have sat well with many given his age and numbers.

If he can provide the goaltending capable of making a deep run, plus sharing the net with Anthony Stolarz, the tandem that won the Panthers their first Stanley of two back-to-back Stanley Cups, to manage his workload, it could work out for both sides. 

Roslovic A Solid Middle-Six Option

Jack Roslovic has always seemed like a good fit for the Maple Leafs. He’s been a decent producer at the NHL level and there’s familiarity with captain Auston Matthews. The Maple Leafs finally made that happen, signing him to a two-year, $8 million dollar deal. 

In back-to-back seasons, he has shown to put the puck in the back of the net as he had 22 goals with the Carolina Hurricanes in 2024-25 and 21 with the Edmonton Oilers last season. He’s a shooter that can do damage in the mid to high danger areas and can be an adept passer. His 186 speed bursts over 20 mph had him in the 93^rd percentile last season, giving him an edge to get ahead and beat opponents very well. 

Roslovic is a player that can move up and down the roster, but serves as a depth scorer in the middle part of the lineup. If he can remain consistent in being a 20-goal, 40-point player, possibly even more than that, this definitely will be a valuable contract and can be a perfect replacement for the offense lost with Matias Maccielli. Roslovic has an opportunity to play alongside Matthews and even though you’re not relying on him for defense, he can produce offense and get results. 

Sissons, Blueger, Duhaime Change Make-Up of Fourth Line

Colton Sissons signed a two-year deal worth $8.5 million, a $4.25 million AAV. At first, I really liked the deal, but the cap hit is worrisome for a fourth line player and is making more than a player with more offensive upside in Roslovic. He had 11 points in 66 games with the Vegas Golden Knights and added another eight points in 22 playoff games last season. He’s primarily going to be used as a defensive specialist; winning faceoffs and playing well in his own end, but also has decent speed, a good shot and can provide a physical presence.  

Teddy Blueger signed a two-year, $5 million contract and Brandon Duhaime signed a three-year, $7.8 million deal with a cap hit of $2.6 million. Blueger spent the last three seasons with the Vancouver Canucks, posting 71 points in 185 games. He’s a shutdown down forward and had good chemistry with Dakota Joshua when he had his breakout season in 2023-24, where he scored 18 goals. Duhaime had nine points in 82 games with the Washington Capitals last season and while that’s not going to be why he’s on the team, he’s a fast skater (78^th percentile in speed bursts over 20 mph) and can play a mean physical style. 

All three bring something different to the table as they look to shake-up the bottom part of the line-up, mainly the fourth line. Sissons combines a power game, but can be a versatile defensive player, win draws and kill penalties. Blueger can bring a strong energy presence and bring that same level of intensity and defensive style. Duhaime is a physical player (159 hits) and definitely can be a tough customer to face when things get ugly.

Overall, given how there were other players who got massive overpayments, Chayka did extremely well to give the fourth line a major overhaul. He got quality players at mostly reasonable prices and addressed a specific area to improve on. 

Paul Trade: One That Needed to Get Done

This one stings because I’m still a big fan of Dennis Hildeby, but the Bobrovsky signing really sealed his fate with the team. If he stayed with the team and didn’t make the roster past camp, he would require waivers and that would risk him being picked up for nothing. Chayka was smart to move on from him now when he had value and get something substantial in return. 

That player being Nick Paul, was a great addition as he too can provide a mix of everything. Strong play in all three zones, a depth point-producer as a possible 40-point player and really makes them deeper up the middle of the ice behind Matthews and John Tavares. He’s a decent finisher, can crash the net and has the speed off the rush to be very dangerous when he finds the open lanes. He had 15 points in 51 games last season, but struggled to stay healthy. He can show up, be a difference maker and help change the tide of a shift and isn’t afraid to mix it up. 

Final Thoughts

Overall, this was an impactful first day of the offseason for Chyaka. He bolstered his crease with the top name available at a reasonable price and term, added a number of depth players with fair value on the open market, aside from the Sissons contract which is a bit of an over payment. In the process, he got a valuable asset in return for a player he would’ve lost later on. 

Chayka isn’t done. Not by a long shot. Even though he made his mark and really wanted to change the make-up and depth of this team, there’s more to be done.

Overall Grade: B