The last two offseasons have been dominated by the signing of one big contract for the Leafs. This year is more complex, and more likely to be filled with a series of minor moves as the puzzle pieces get shifted around to create whatever final form Kyle Dubas has in mind for the team.

Dubas got an early start with the Kasperi Kapanen trade landing very early in the playoffs, but there’s a lot more to be done. GMs don’t always get to decide what order things happen in, however; deadlines always shape their thinking to some extent.

October 9 is the likely date for free agency to begin, and that’s the big deadline. The other is October 6 when Qualifying Offers to RFAs are due, with a lot needing to happen in those three day, the to-do list goes something list (numbers from CapFriendly):

  1. With Kapanen gone, his replacement on the PK and on the wing, Ilya Mikheyev, needs a contract. He’s an RFA with arbitration rights, so if he wants to push it, that could delay the final number on his deal until November. Brendan Shanahan sent a message in his post-season presser when he talked about how it’s not fair, but a poor playoffs will affect his contract. Dubas will want this sorted out more quickly and with a team friendly result. The QO is only $874,125, but the final deal seems likely to be one million - something. The tricky part is the something. I expect this signing any day now, but you never know.
  2. Newly acquired Evan Rodrigues needs a deal done before the QO is due because the Leafs aren’t going to get trapped into paying him either $2 million or an arbitration award. They didn’t take him in trade with the plan to just dump him, however. His deal might be the very next thing resolved, too, because if he wants to play on his hometown team, he has to know he needs to make a deal now that will let him prove that arbitrator’s award of $2 million wasn’t grossly inflated by ice time on a bad team. One year takes him to UFA status, so a cheap show-me contract could pay off for him next year. His alternative is to become a UFA one year early coming off a very bad season, so I think he’ll play ball.
  3. Travis Dermott could get signed before the QO goes out too. His salary amount is the same as Mikheyev’s, it’s just one-way instead of two-way. I think it’s in his interests to just take that one-year QO and kick the negotiation to next season, but he might want the security of a two-year deal now. It’s also not going to be large, and he has to decide how much he wants to play for the Leafs for the next couple of years. I don’t believe there’s any good reason for the Leafs to set out to trade him, but they aren’t likely to say no to a deal that includes him if it’s in their interests.
  4. There’s other RFAs to sign, notably Denis Malgin and Frederik Gauthier. Gauthier is likely to sign a two-year minimum salary deal, which would make his AAV less than his salary in year two, something cap-strapped teams like. (Teemu Kivihalme’s deal is exactly this.) Malgin didn’t stick very well in the lineup after arriving in trade, and while he has arbitration rights, you can’t take a record like his to arbitration and come out the winner like Rodrigues did. He has had some good results in very limited usage in the past, and some fans like him because he’s the type of player they want to see on the ice, but he couldn’t take a lineup spot from Nic Petan, and that’s pretty much the recipe for a cheap depth deal or a flight back to Switzerland.
  5. Jason Spezza is likely to be re-signed, but there’s not a lot of time pressure to do that right away.
  6. Dubas has to decide if he wants Kyle Clifford or not. He would likely announce ahead of the free agent date if the answer is no so Clifford can get other teams interested.
  7. There are a host of NHL-contracted AHLers expiring as UFAs, and with Dubas on the AHL’s Return to Play committee, he will know how much effort he and Laurence Gilman need to put into sorting out the AHL roster. Normally that happens in the spring as college and junior players graduate off of teams, and then heats up just as training camp starts. This year, it feels like this might be a very last minute job.
  8. Two AHLers are RFAs. One is Max Veronneau, whose arbitration rights coming off his ELC at 24 and his skill in the AHL make him worth signing early for something, maybe even his Qualifying Offer amount of $874,125. The other is Jeremy Bracco, who is at a crossroads in his career, and I can’t predict what will happen to him.
  9. You may have heard that Dubas needs to find a defenceman. I’m not sure if that should be number one here or the last thing on the list, but it’s really what all the rest of this list is about. All of these peripheral players need to be squeezed, to be blunt, to make room for someone who matters a lot more. Someone who is at least better than Holl and approaching Jake Muzzin’s ability if not even better.
  10. Dubas does not need to find more depth third pairing guys. There are at least nine NHL-probable defenders on the roster. That’s plenty at the bottom end. He doesn’t need to morph Dermott into a right-shooter of the same ability, either, because it’s just not enough of a difference to matter. If there are borderline top-four defenders out there like Dermott who can be had for low cap hits, that’s worth pursuing, but cheap depth is not the job here. A difference-maker is.