First step is to understand the conditions of the Florida pick to Calgary:
If this year Florida's pick is top 10, then the 2025 Florida 1st goes to Philly and 2026 Florida first to Calgary. This is unlikely, so:
Lets assume the 2025 Florida 1st goes to Calgary (also lottery protected)
Now its up to the Habs to decide:
1) If Calgary's own pick is 20-32, Habs can opt to take it. This is very unlikely and even if it happens, the Habs would be dumb to take it, so forget this one too
2) Assuming Calgary gets Florida's first in 2025 and assuming the habs do not opt for the 2024 pick (20-32) then Montreal gets the better pick between Florida and Calgary 2025 first, unless Calgary's is top 10, in which case they get Florida's.
Above point no.2 is the most likely at the moment, that is Habs get the better of Calgary and Florida's 2025 unless Calgary's is top 10 then Florida. However:
Worst Case scenerio for the Flames:
Florida misses the postseason in 2024, Calgary gets Florida's 2026 pick, Montreal gets Calgary's 2025 pick unless it is 1st overall.
Florida misses the postseason in 2025, Montreal gets the better of Florida or Calgary, guaranteeing a lottery pick.