The Toronto Maple Leafs were one of the busiest teams in the league on day of free agency, signing six players to contracts and swinging two trades.

From the crop of free agents they signed, the headlining name was goaltender Sergei Bobrovsky, while the trade front saw a swap with the Tampa Bay involving Dennis Hildeby and Nick Paul, and Nick Robertson found himself traded to the Pittsburgh Penguins to reunite with former GM Kyle Dubas. The remainder of the signings consisted mostly of bottom-six forwards including Jack Roslovic, Colton Sissons, Teddy Blueger, and Brandon Duhaime.

While there was a clear motive based on the types of players the Leafs targeted, which was to fill the bottom six with speed and penalty killers, some of the contracts raised alarm bells with sections of the fanbase. Let’s break down each player’s production in 2025-26 and what they signed for.

Some important notes for context that I couldn’t fit in the table — Bobrovsky recorded a save percentage (SV%) of .877 with a goals-against average (GAA) of 3.07 and a record of 27-23-1 with the Florida Panthers last season. His 2025-26 was objectively a down-year, and the Leafs are clearly banking on the rest of his resume with this contract. Also, Blueger recorded those totals in 35 games, which makes those numbers look a lot more appealing, and MacEwen only played three NHL games last season, so he’s probably more of an option for the Marlies.

Now that we’ve got that out of the way, what do you notice about these contracts?

I’m not writing this in real time, so I can’t wait for you to submit an answer, but if you guessed the length of the contracts, you’re correct. Nothing shorter than two years, and nothing longer than three.

What this tells me about the Leafs’ activity in free agency is that the directive from the top is to rebound and push for a Stanley Cup the same way they have been since the start of the Auston Matthews era. In 2025-26, there was far too much responsibility on Matthews to carry the weight defensively and not nearly enough speed. The Leafs clearly want to get Matthews back to playing the 60-goal hockey he’s proven capable of on more than one occasion, and the best way to do that is to let guys like Sissons, Duhaime, and Blueger handle penalty-killing duties while letting the top goal scorer do things that a top goal scorer should do. Meanwhile, Roslovic is somebody who can jump into the top six if needed, he has chemistry with Matthews, and Paul should be able to put in work both offensively and defensively.

At the same time, the Leafs have strategically mapped out these contracts to expire when there are bigger signings to worry about. Namely, the end of Matthews’ current deal (two years from now) and the end of first overall pick Gavin McKenna’s entry-level contract (three years from now). It’s a pretty significantly different game plan than the one we saw out of former general manager Brad Treliving, who would add years to the contract to get the annual price down (see the Chris Tanev contract).

When you look at it through that lens, the fact that guys like Sissons (who’s typically more of a 30-point player) got as much as they did makes sense. And at some point, we have to get used to the reality of the rising salary cap. I was shocked when I saw the Leafs give $4.25 million to a player who won’t play any higher than the third line, and then I remembered that the Chicago Blackhawks gave Bowen Byram $12.5 million a year despite a history of concussion issues and a career high of 42 points. The league is adapting to a rising cap, and soon, the media and fans will, too.

I also saw some complaints that the bottom-six is full without leaving any space for Marlies players such as Jacob Quillan, Luke Haymes, or Ryan Tverberg to claim a spot on the roster. While I can understand that, given the Marlies recent success and the fact that they would come at a cheaper price, the Leafs aren’t in a position where they can let unestablished players figure it out if they don’t get used to the speed of the NHL right away. If Chayka only signed half of the players he did yesterday and banked on somebody like Quillan filling the fourth line role, and it ends up that he needed more time in the AHL, then you have to spend assets to acquire the same players they signed on Wednesday. In that same breath, injuries will always happen. These Marlies players will get a chance to show what they can do at the NHL level, and if they outplay the veterans, those veterans are on the types of deals that can be flipped to contenders at the deadline for draft picks.

For better or for worse, the Leafs are clearly looking to turn their fortunes as soon as next season and make as much of a push as possible to bring a Cup back to Toronto before they have to worry about Matthews and McKenna’s next deals. The latter being on an entry-level contract is a bit of a cheat code for them, especially if he develops at the rate he’s expected to, and as much as it may seem like the Leafs blew their wad on the first day of free agency, these contracts are organized in a way that shouldn’t hamper them financially down the road, which is a welcomed change of pace in Toronto.