Thursday afternoon, Kent Hughes acquired Sean Monahan and a conditional first-round selection from the Calgary Flames in exchange for future considerations. The news first began trickling out around mid-afternoon in the Eastern Time Zone, but hours rolled past without any official confirmation. The extended delay sent speculation into overdrive, especially since the Montreal Canadiens at the time did not appear to have a logical way to accommodate Monahan’s cap hit.
The reality, as it often is, was more benign than the speculation. No three-plus-team deals, no Pierre-Luc Dubois, no Jonathan Drouin. However, that doesn’t mean that the delay wasn’t understandable. When the trade was formalized and officially announced, the world saw a set of terms and conditions attached to the first-round selection that would make lawyers have a second look. The description was so labyrinthine that a flowchart was necessary—for a trade involving, at its heart, one player and one pick.
Here is a flowchart to decipher the logic paths of the Sean Monahan trade to Montreal. #GoHabsGo pic.twitter.com/onL7JMWURp
— Andrew Zadarnowski (@AZadarski) August 19, 2022
Let’s break down the possible scenarios and the Habs’ best- and worst-case situations in all of them.
Scenario 1
Calgary finishes top-12 in the NHL in 2024
If the Flames’ first-round draft selection in 2024 is positioned between #20 and #32, the Canadiens have the option to choose that pick as compensation for acquiring Sean Monahan.
Best possible outcome in this scenario: The Canadiens acquire the 20th overall selection in 2024.
Worst possible outcome in this scenario: The Flames win the Stanley Cup in 2024, and the Canadiens acquire the 2024 32nd overall selection.
Note: Scenarios 2 through 5 assume that the Canadiens could or did not elect to obtain Calgary’s 2024 first-round pick.
Scenario 2
Calgary does not finish top-12 in 2024 AND the Florida Panthers do not hold a selection between #1 and #10 in 2025.
If the Canadiens elect not to acquire the Flames’ 2024 first-round selection, the question of the pick is then deferred to 2025. The Flames acquired the Panthers’ 2025 first-rounder as part of the exchange for Matthew Tkachuk, but that selection is top-10-protected.
If Calgary holds both its own selection and Florida’s selection, and both selections are not in the top-10 of the 2025 NHL Entry Draft, Montreal will receive the earlier of the two picks. If Calgary’s selection is in the top-10 of the draft but Florida’s is not, Montreal will receive Florida’s pick.
Best outcome: Montreal receives the 11th overall selection in 2025.
Worst outcome: Calgary and Florida meet in the Stanley Cup Final, and the Canadiens acquire the 2025 31st overall selection.
Scenario 3
Florida holds a selection between #1 and #10 in 2025.
If the Panthers selection is subject to top-10 protection, Montreal will receive Calgary’s 2025 first, provided that the Flames do not select first overall.
Best outcome: Montreal receives the second overall selection in 2025.
Worst outcome: The Flames win the Stanley Cup in 2025, and the Canadiens acquire the 2025 32nd overall pick.
Scenario 4
Calgary does not hold a top-10 pick in 2025 AND the Florida Panthers do not hold a selection between #1 and #10 in 2025 — but the Calgary Flames do not have ownership of this pick.
If Calgary would normally be in possession of Florida’s first-round selection in 2025 but have traded that selection to another club, Montreal is entitled to receive an additional fourth-round selection (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 (Round 4, Pick 11) selections in 2025.
Worst outcome: The Flames win the Stanley Cup in 2025, and the Canadiens acquire selections #32 and #128 (Round 4, Pick 32) in 2025.
Scenario 5
Calgary holds the first overall selection in 2025.
If the Flames’ own selection in 2025 is first overall, the Canadiens’ compensation for acquiring Sean Monahan is deferred to 2026. In exchange, Montreal acquires the Flames’ own third-round selection in 2025.
There is the possibility that the Flames may hold two first-round selections in 2026, as Calgary will acquire Florida’s first-round selection in 2026 instead of 2025 if the 2025 pick is subject to top-10 protection. In this circumstance, Montreal will receive the earlier of the two selections.
Best outcome: Montreal receives the 97th (Round 4, Pick 1) selection in 2025 and first overall selection in 2026 after the Flames finish last in the NHL.
Worst outcome: The Flames and Panthers both go worst to first, moving from lottery selections in 2025 to meeting in the Stanley Cup Final in 2026, leaving the Canadiens with the 97th pick in 2025 and the 31st in 2026.
Reading these potential outcomes, it seems that Hughes has done well in covering all his bases. The terms and conditions do two things: {1) they prevent the Habs from losing out on a better draft pick because the Flames have cashed in on Florida’s draft pick after realizing that they couldn’t hold it anyway, and (2) they increase in potential reward for Montreal the longer Calgary defers. The best possible draft position moves from 20th in 2024, to second in 2025, and first in 2026. Moreover, it is the Canadiens, not the Flames, who hold the key to gate-guarding the biggest potential jump; there is no way for the Flames to force the Canadiens to take a 2024 pick that would be no higher than 20th.
Of course, Hughes now creates yet another thing for Habs fans to argue about: Which draft class is the best one for the Canadiens to hold Calgary’s pick?
