Breaking down the conditions in the Sean Monahan trade

Seeing conditional draft picks get dealt is commonplace in this day and age. However, the stipulations on them are usually easy enough to understand. Whether it’s a third-round pick dropping down to a fourth if a player doesn’t play enough games for their new team, or a second-round pick upgrading to a first if the team in question wins the Stanley Cup, the conditions on trades are sensible, at least for the majority of the time.

The Montreal Canadiens seem to buck that trend, though. Starting with some lengthy conditions on the Christian Dvorak trade prior to last season, the Canadiens have agreed to an even more complex (and frivolous, depending on who you ask) set of conditions on the 2025 conditional first-round pick that they acquired Thursday from the Calgary Flames, along with Sean Monahan. So much so that it’s worth its own post, with reference drawn from CapFriendly’s posting and reporting on the topic.

There are three possible umbrella scenarios that could determine which draft pick Montreal actually receives:

Scenario 1: If Calgary’s 2024 first-round pick falls between 20th and 32nd overall, Montreal can elect to receive Calgary’s 2024 first instead of their 2025 first.
Scenario 2: Calgary receives the 2025 lottery-protected first-round pick sent to them by the Florida Panthers in the Jonathan Huberdeau trade.
Scenario 3: Calgary does NOT receive Florida’s 2025 lottery-protected first-round pick.

Scenario 1

This is easily the simplest and potentially most likely scenario if the Flames are still rolling strong two years from now. If Montreal opts to swap out an unknown 2025 first-rounder for a late 2024 first-rounder, then the trade tree ends and Montreal receives no additional compensation.

Scenario 2

Now, things get complex with the addition of Florida’s 2025 lottery-protected first-round pick. In the event that both the Flames’ and Panthers’ 2025 first-round picks are NOT in the top 10, the Canadiens will receive the better of the two selections.

However, if the Flames’ 2025 first-round pick is a top-10 pick and the Panthers’ pick is not, Montreal is guaranteed to receive the Panthers’ pick. If the opposite is true, Montreal will receive Calgary’s selection.

Scenario 3

This is the most unlikely yet most complex scenario. If Florida’s 2025 first-round pick ends up as a top-10 choice, they’ll retain the pick and send their 2026 first-rounder to Calgary instead. This has two possible implications for Montreal:

If Calgary’s 2025 first is NOT top 10: Montreal will receive Calgary’s 2025 first-round pick, and, if Florida’s 2025 first-round pick is not top-10, but was transferred to another team due to prior conditions AND is a better pick than Calgary’s, Montreal will also receive Calgary’s 2025 fourth-round pick as compensation.

If Calgary’s 2025 first is top 10: If Calgary’s 2025 first-round pick is first overall, Montreal will receive the better of Florida’s and Calgary’s 2026 first-round picks AND Calgary’s 2025 third-round pick. If Calgary’s 2025 first-round pick falls between selections two through 10, Montreal will receive the pick.

All in all, if the reported conditions are correct, the Canadiens have the potential to receive one of the following five outcomes:

2024 Calgary first-round pick
2025 Calgary first-round pick + potential 2025 Calgary fourth-round pick
2025 Florida first-round pick
2026 Calgary first-round pick + 2025 Calgary third-round pick
2026 Florida first-round pick + 2025 Calgary third-round pick