A soft deadline for Rasmus Sandin has passed us by. August is over, the slowest month in the hockey calendar, where the usual run of things is for the list of unsigned RFAs to dwindle to the seriously difficult negotiations by Labour Day. So it has been with only 11 RFAs other than Sandin unsigned. They are:

  • Alex Formenton, OTT
  • Jason Robertson, DAL
  • Ryan McLeon, EDM
  • Kirby Dach, MTL
  • Sean Durzi, LAK
  • Barrett Hayton, ARI
  • Michael Anderson, LAK
  • Nick Hague, VGK
  • Adam Ruzicka, CGY
  • Cayden Primeau, MTL
  • Parker Wotherspoon, NYI/

Some of these players may have already agreed to a deal, but the contract can’t be registered until the team actually had cap space. STOP! Do not go to Cap Friendly and look at the cap space. That’s an in-season projection that will be finalized by October 11, and until then everyone is running on off-season cap space with a 10% overage cushion and a totally different structure to the calculation of which contracts count against the cap.

All you need to know is that the Leafs are not waiting because of cap room, they have masses of it right now. October 11 is another story. Note: the NHL season actually starts with some games in Europe on October 7 and 8. The league stated the official opening day is October 11. Most teams begin play on October 12 or 13. So when are cap compliant rosters due, exactly? I’m going with a guess of October 10 until that is clarified further.

Labour Day is a soft deadline because it marks the end of goof-off season. So what is the hard deadline? We should all remember this one down to the minute. At four minutes to 5 pm Eastern Time on December 1, 2018, a Swedish reporter for Aftonbladet tweeted: Hör att Lill-Nyllet är signad med Maple Leafs. Nära 7miljoner usd per år.

I was so convinced Nylander would sign that, at ten to five, I had only just opened an article to start writing an article saying that the 5 pm deadline had passed and Nylander could not play for the Leafs all year. I saw the tweet and started capslocking in our chat, and everyone else was all... Who is this guy? What the hell is a Lill-Nyllet? And I started explaining about weird Swedish nicknames until finally I just all-capsed at everyone: I’M GOING WITH IT

One minute later, Darren Dreger had the news so people who don’t know what the hell an Aftonbladet is were happy that it was real. Bob McKenzie came in at one minute to five with the AAV.

December 1 at 5 pm is the hard deadline, and now that we’re back on a normal NHL schedule it is the deadline for Sandin to sign. (He has the same agent as Nylander if you want to worry we do the five to five thing again.)

And I mean hard deadline. No it doesn’t matter if this or that happens, and there is no clever scheme to wiggle out of it. If a player is not on their team’s roster at that moment, they don’t play all year, including playoffs. In the 86 days after today at 5 pm, a deal has to be made.

The next closest semi-soft deadline is opening day of the regular season, or more properly, the day before when cap-compliant rosters are due. Signing after the season begins makes the first year of the contract have a larger AAV — something else we should remember from the Nylander deal — and the Leafs don’t want that to happen with Sandin. The cap is way too tight this year. Before October 10, they have just enough time to sort things out to fit whatever deal they do sign in with a roster of at least 20 players. So the next 34 days are more likely to be when the contract will be signed.

The soft deadline that comes before that one is the start of training camp. Most veterans don’t care if they miss camp, and some would consider it a bonus, but for Sandin, you have to figure he really wants to get in there, play preseason games and get his hands solidly on a roster spot. We don’t have an exact date yet, but training camp should begin around September 21, three days before the first preseason games. That’s 15 days from now. Mitch Marner graciously took a tiny discount off of the Matthews’ deal AAV and signed on September 13 in 2019, just in time to get on the plane to get to training camp in St. John’s. We might get a deal like that again.

What will happen is anyone’s guess, so here’s mine to start you off. I don’t think the Leafs’ plan to trade anyone unless they’re forced to. This is not a bad stance, because depth is good. If training camp gifts them with a short-term injury or two, they can coast for a few weeks with more players than you’d think possible. A few weeks can easily turn into a few months as happened last year. Some of their defence depth might get lost on waivers as well, so moving someone out just for cap space would be less than idea.

Given all of that, I think the Leafs want Sandin under contract well before October 10. They want September 21 or so to be the deadline in their minds. So I think this is a two-week problem not an 86 day marathon. That’s the best outcome for Sandin too. It feels like they’re converging on the equinox like a pair of teenagers heading to the last music festival of the summer.

Of course there is another way this resolves, and late summer is also classic breakup season.

My favourite version of this song because I love Rufus, but also, he gets that this song is really about a relationship that might be broken.

How’s it going to end? Your guess is totally as good as mine.