There are 2 - 5 games remaining in the Stanley Cup Final, and when that ends, one team is very happy, and the other 31 teams get to work.
There are some meetings in early June of the NHL executive, which might be mostly concerned with the sale of the Ottawa Senators, but the other issue on the table is the salary cap.
Gary Bettman, at the opening of the SCF, once again said the cap won't go up by more than $1 million because the player escrow debt is not quite paid off. This was, once again, reported as news and some kind of final word on things. Once again, the door is still open to a negotiated step-up amount to ease the transition into the 2024-2025 cap amount which will be substantially higher and have a very, very large increase if some of that isn't added to the cap now. Clarity on this won't come for a couple of weeks. The real final number is always known before the draft, and never before about June 18.
Most of these dates are on the calendar on the PPP Leafs mainpage if you want to refresh your memory.
June 15 to 21
The later of June 15 or 48 hours after the SCF is when the first buyout window opens. I'll have a post up for you soon with details, but for now, what you need to know is players without a no-move clause have to clear waivers first before a buyout. This window closes on June 30.
This is also the deadline for team-elected salary arbitration – 5:00 pm on whatever date it ends up being for both.
June 28 & 29
NHL Entry Draft. Round one is on the first day in the evening, all other rounds are the next day. The draft is in Nashville, which is one hour behind Toronto time.
Buyout period ends and Qualifying Offers are due – both at 5:00 pm. We'll have more on QOs and the RFAs needing contracts in the coming days.
Offer sheet discussions can begin as of 7:00 pm this date with RFAs who have received a QO.
Free Agent Day opens at noon. All RFAs and UFAs can be signed. RFAs can accept qualifying offers, and players like Auston Matthews who are eligible to sign extensions can magically negotiate it in 10 minutes and sign at ten past twelve.
July 5 & 6
Player-elected arbitration deadline is at 5:00 pm on July 5. At that time a 24 hr window for teams to elect arbitration opens and closed on July 6.
Qualifying Offers expire – this does not make the RFA a free agent, they just can't accept the offer any longer and must negotiate a deal.
Salary arbitration begins. It should end sometime in early August, no later than August 4. Teams can get a second buyout window if they have an arbitration case.
Deadline for college drafted players. The Leafs have one this year, Ryan O'Connell, who they have no reason to sign.
And that's the basic schedule, we'll detail the RFA situation closer to the end of June, and of course, once those three or four prospects are drafted, we'll have the T25 list to argue about in August.