Reality, as is often the case, was more favorable than speculation. No deals with more than three teams, no Pierre-Luc Dubois, no Jonathan Drouin. However, that doesn’t mean the delay wasn’t understandable. When the trade was formalized and officially announced, people saw a set of terms and conditions attached to the first-round pick that would make lawyers take a second look. The description was so labyrinthine that a flowchart was necessary—for a transaction that involved, at its heart, a player and a pick. Let’s break down the possible scenarios and the Habs’ best- and worst-case scenarios in all of them.
Scenario 1
Calgary finishes top 12 in NHL in 2024
If the Flames’ 2024 first-round draft pick lands between #20 and #32, the Canadiens have the option to select that pick as compensation for acquiring Sean Monahan. The best possible outcome in this scenario: The Canadiens get the 20th overall pick in 2024. The worst possible outcome in this scenario: The Flames win the Stanley Cup in 2024 and the Canadiens get the 32nd overall pick in 2024. Note: Scenarios 2 through 5 assume the Canadiens could or did not choose to acquire Calgary’s 2024 first-round pick.
Scenario 2
Calgary doesn’t finish in the top 12 in 2024 AND the Florida Panthers don’t have a pick between #1 and #10 in 2025.
If the Canadiens choose not to acquire the Flames’ 2024 first-round pick, the pick is then deferred to 2025. The Flames acquired the Panthers’ 2025 first-rounder as part of the trade for Matthew Tkachuk, but that pick is top-10-protected. If Calgary owns both its pick and Florida’s pick, and both picks are not in the top-10 of the 2025 NHL Entry Draft, Montreal will receive the earlier of the two picks. If Calgary’s pick is in the top-10 of the draft but Florida’s is not, Montreal will get Florida’s pick. Best outcome: Montreal receives the 11th overall pick in 2025. Worst outcome: Calgary and Florida meet in the Stanley Cup Final and the Canadiens get the 31st overall pick in 2025.
Scenario 3
Florida has a pick between #1 and #10 in 2025.
If the Panthers pick is subject to top-10 protection, Montreal will get Calgary’s 2025 first, provided the Flames don’t pick first overall. Best outcome: Montreal receives the second overall pick in 2025. Worst outcome: The Flames win the Stanley Cup in 2025 and the Canadiens get the 32nd overall pick in 2025.
Scenario 4
Calgary does not own a top-10 pick in 2025 AND the Florida Panthers do not own a pick between #1 and #10 in 2025 — but the Calgary Flames do not own that pick.
If Calgary would normally have had Florida’s first-round pick in 2025, but had traded that pick to another club, Montreal is entitled to receive an additional fourth-round pick (Calgary’s own) in 2025. This condition only applies if Florida’s first round draft position in 2025 is better than Calgary’s, and if Calgary’s first rounder is not a top-10 pick. Best outcome: Montreal receives the 11th and 107th overall picks (Round 4, Pick 11) in 2025. Worst outcome: Flames win Stanley Cup in 2025 and Canadiens acquire picks #32 and #128 (Round 4, Pick 32) in 2025.
Scenario 5
Calgary owns the first overall pick in 2025.
If the Flames’ own 2025 pick is first overall, the Canadiens’ compensation for acquiring Sean Monahan is deferred to 2026. In exchange, Montreal gets the Flames’ 2025 third-round pick. There is a possibility that the Flames will carry two first-round picks in 2026, as Calgary will acquire Florida’s 2026 first-round pick instead of 2025 if the 2025 pick is subject to top-10 protection. Under these circumstances, Montreal will receive the former of the two options. Best outcome: Montreal receives the 97th (Round 4, Pick 1) pick in 2025 and the first overall pick in 2026 after the Flames finished last in the NHL. Worst outcome: The Flames and Panthers both go worst in the first, moving from lottery picks in 2025 to the Stanley Cup Final in 2026, leaving the Canadiens with the 97th pick in 2025 and 31st in 2026. Reading through these possible outcomes, it seems that Hughes has done well in covering all of his bases. The terms and conditions do two things: {1) prevent the Habs from losing out on a better draft pick because the Flames cashed in on Florida’s draft pick after realizing they couldn’t keep it anyway, and (2) increase in potential reward for Montreal’s longest postponement of Calgary. The best possible draft position moves from 20th in 2024, to second in 2025 and first in 2026. Plus, it’s the Canadiens, not the Flames, who hold the key to gatekeeping the biggest potential jump. there’s no way for the Flames to force the Canadiens to pick in 2024 that wouldn’t be higher than 20th. Of course, Hughes now creates another thing for Habs fans to argue about: Which draft class is the best for the Canadiens to get Calgary’s pick?
