Earlier today we got the news that the NHL had moved up its entry draft. Not surprisingly the decision to move up free agency followed shortly after.

Initially it seemed that the move for the draft dates might have been to give GMs a bit of breathing room between the draft and free agency, and to give teams and players a chance to enjoy the Thanksgiving (or Columbus Day) weekend without having to worry about sitting by the phone, but alas. The NHL has traded Canada Day free agent frenzy for a Thanksgiving Frenzy instead.

One of the biggest questions for me is when are teams expected to extend qualifying offers to their restricted free agents, and when will they be required to announce club elected salary arbitration. With the tight timelines, that may be key and I’d expect the free agent market to improve significantly in the 11th hour due to the inclusion of unqualified RFAs. Oh and the buyouts, while the Leafs won’t be buying anyone out, we should be curious about when those start, which normally comes 48 hours after the close of the playoffs.

The Leafs have a few free agents they’ll need to sort out in the next month.

As far as unrestricted free agents go, we’ve likely seen the last of Tyson Barrie, Cody Ceci, Kevin Gravel, and LTIR darlings Nathan Horton and David Clarkson are officially gone. Marlies UFAs like Garret Wilson, Mikko Salomaki, and Matt Lorito are probably gone as well.

It’s a bit tougher decision for players like Jason Spezza, Kyle Clifford, and Tyler Gaudet.

Spezza, is obviously a fan favourite, and has been very vocal about wanting to return. He played at the league minimum last season, and the only reason this could be complicated is if he’s looking for a raise, wanting term, or requires assurances about playing time the Leafs aren’t comfortable with.

Clifford is a bit more complicated in that the Leafs probably want him back, but he’s potentially expensive for a fourth line winger and by bringing him back the Leafs would be giving up a 2021 2nd round pick instead of a 2021 3rd to the Kings for the trouble. I don’t think that’s something the Leafs should want to do, and to further add intrigue to it, Clifford recently took the Leafs off his twitter profile.

Gaudet is a Marlies depth player, but one with a history with Dubas and Keefe. There’s no reason to believe they wouldn’t bring him back, and as we saw in the return to play training camp, there is potential he could get a look as a depth forward.

The RFA list is a bit longer, and no less complicated. Travis Dermott and Ilya Mikheyev will certainly be qualified, but in Mikheyev’s case, he is arbitration eligible and that complicates things. Evan Rodrigues is a player I’m sure the Leafs would love to add to their roster, but his $2M qualifying offer price tag prices him out of Toronto already. I don’t think we’re at the end of the Freddie Gauthier era in Toronto, but he is on the borderline of getting qualified as well as the Leafs have too much depth to make a case for Gauthier continuing on their fourth line.

Players like Kaskisuo and Veronneau could be back in Marlies roles, but it seems unlikely, while Denis Malgin and Jeremy Bracco are as good as gone.

What should the Leafs do with Jason Spezza?

What should the Leafs do with Ilya Mikheyev?

Travis Dermott is the defensive domino

As for free agency targets for the Leafs, well that seems to begin and end with right handed defensemen, but there is also a good chance the Leafs pursue some veterans looking to win now, provided they are on cheap contracts, and some physical depth that can do more than just hit. The flat cap providing the biggest challenge to all of this.

5 Defensemen not named Alex Pietrangelo that the Leafs might consider signing

There’s also the small matter of what the Leafs do with Andersen and if anyone else besides Kapanen will be shipped out.

So we’re 31 one days away from free agency, 28 days until the draft, and the Leafs have a GM with an itchy trigger finger. Seems like it should be a fun September.