Ideal Scenario For Canadiens Sean Monahan Trade Conditions

When the Montreal Canadiens acquired Sean Monahan in the summer of 2022, they created the most complicated trade in modern NHL history.

The Canadiens acquired Sean Monahan and his $6.375M contract from the Flames along with a conditional 2025 1st-round pick that has confused fans for months. That’s because, on top of the many conditions surrounding this specific trade, previous trades made between the Florida Panthers, Calgary Flames

We’re here to help break it down for you.

Before we even get started with the conditions, it’s important to note that there are three possible scenarios:

1. Swapping for the Flames 2024 1st-round pick (if the pick is between 20th and 32nd overall)
2. Conditions where the Flames receive the  Florida Panthers’ lottery-protected 2025 1st-round pick (Matthew Tkachuk trade)
3. Conditions where the Flames don’t receive the Florida Panthers’ lottery-protected 2025 1st-round pick

But First, Let’s Talk About Florida

The Florida Panthers factor into this trade, because their 2025 1st-round pick was included in the upcoming conditions.

After trading their 2024 1st round pick to the Philadelphia Flyers prior to the 2022 NHL Trade Deadline in a package to acquire Claude Giroux, they then traded their 2025 1st round pick to the Flames last summer in a package for Matthew Tkachuk. Each of those picks came with their own conditions;

• Florida’s 2024 1st round pick: If the pick is a top-10 selection at the time of the 2024 NHL Draft, the Flyers would instead receive the Panthers’ 2025 1st round pick and the Flames would receive the Panthers’ 2026 1st round pick.
• Florida’s 2025 1st round pick: If this pick were to be a lottery pick (top-16), Calgary would instead receive the Panthers’ 2026 1st round pick.

Should either of the Panthers’ conditional picks be bumped a year due to subpar performances, it would create a chain reaction that will impact the Montreal Canadiens.

Let’s begin to unpack all this:

Scenario #1: Montreal Canadiens Swap 2025 1st-round pick for 2024 1st-round pick

This is perhaps the simplest scenario of all. If Calgary’s 2024 1st round pick falls between 20 and 32 inclusively, Montreal will have up to 48 hours before the 2024 NHL Draft to decide to take this pick.

However, based on early-season play and current NHL betting odds, this scenario might not even be available to the Montreal Canadiens, as the Flames currently sit 2-6-1 on the season.

Should things continue in this direction, their 1st-round pick will likely be out of range, and thus we move to the 2025 conditions.

Scenario #2: If Calgary receives Florida’s 2025 1st-round pick

Assuming the Florida Panthers 2024 1st-round doesn’t land in the top-10 of the 2024 NHL Draft or that they miss the playoffs in 2024-2025, the Calgary Flames will receive Florida’s 2025 1st-round pick. This ensues the following conditions:

• If neither of Calgary or Florida’s 2025 1st round picks are in the top-10
  • Montreal will receive the better of the two 2025 1st-round picks.
• If Calgary’s pick is in the top-10 and Florida’s is not
  • Montreal will get Florida’s 2025 1st round pick.

Scenario #3: If Calgary does not get Florida’s 2025 1st-round pick

In this scenario, Florida’s 1st-round pick is either a top-10 selection in 2024 or a top-16 selection in 2025. If either of these outcomes occurs, Florida will have the option of sending Calgary their 2026 1st-round pick instead of their 2025 1st-round pick.

With only their 2025 1st-round pick in tow, the Flames’ compensation to the Canadiens would go as follows:

• If Calgary’s 2025 1st-round pick isn’t in top-10
  • Montreal will receive Calgary’s 2025 1st.
  • Montreal could also receive an additional 2025 4th-round pick if:
    • Florida’s 2025 1st round pick isn’t a top-10 pick.
    • Florida’s 2025 1st rounder has been transferred to another club (to Flyers or traded after lottery win).
    • Florida’s 2025 1st round pick has a higher draft position than Calgary’s 2025 1st round pick.

• If Calgary’s 2025 1st round pick is a top-10 pick, but not the 1st overall
  • Montreal receives Calgary’s 2025 1st round pick.

• If Calgary’s 2025 1st round pick wins the NHL Draft Lottery for the 1st overall pick, Montreal gets
  • Calgary’s 2025 3rd round pick.
  • The better of Calgary or Florida’s unprotected 2026 1st round picks.

Ideal Scenario for Montreal Canadiens?

With the way the Flames have been playing of late, and the long list of unrestricted free agents they currently have, the club sits at a crossroads of doubling down on their aging core or starting, at worst, a retool to bounce back in a season or two.

That could mean that the Flames’ 2025 1st could be more valuable than picks 20-32 in the 2024 NHL Draft (Scenario #1) or, at best, the 11th overall pick in 2025 with (Scenario #2).

For the Canadiens, the scenario with the most amount of upside would be Scenario #3.

With Scenario #3 the Montreal Canadiens would Calgary’s 2025 1st, which could go as high as 2nd overall in 2025 or, in the event that the Flames win the 2025 NHL Draft lottery and pick 1st overall, an unprotected 1st in 2026 from either Florida or Calgary.

Many possibilities remain, but there still remains a lot of hockey to be played, and, after reading this, a lot of Advil to be consumed.