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Official: Montreal Canadiens Acquire Sean Monahan and Conditional 1st for Future Considerations

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Jon
August 18, 2022  (6:09 PM)
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The Montreal Canadiens have officially announced that they have acquired C Sean Monahan and a conditional first-round pick in exchange for future considerations:

The move clears salary cap space, allowing the Calgary Flames to sign top free agent Nazem Kadri to a seven-year, $49 million contract. The list of conditions on the first-rounder Montreal receives explains why the deal took forever to get announced. Lets go over them:

"1. In the event Calgary's own 2024 first (1st) round choice is selection 20-32 (inclusive) (following the determination of the 2024 NHL Draft lottery results), then Montreal shall have the option, exercisable until 48 hours prior to the start of the 2024 NHL draft, to exchange the conditional 2025 or 2026 first round choice to become Calgary's own 2024 first (1st) round choice); or,

If Florida's 2025 First (1st) Round Choice Transfers to Calgary (pursuant to the conditions on an earlier trade)

2. In the event the conditions to trigger Montreal's option as noted in #1 above does not occur, or Montreal declines to exercise this option, the following conditions shall prevail:

A) If both Calgary's own 2025 first (1st) round choice and Florida's 2025 first (1st) round choice (previously acquired by Calgary) are not in the top-10 selections of the 2025 NHL Draft (following the determination of the 2025 NHL Draft lottery results), then Montreal shall receive the earlier of the two (2) stated choices; or,
B) If Calgary's own 2025 first (1st) round choice is a top-10 selection and Florida's 2025 first round selection (previously acquired by Calgary) is outside of the top-10 selections (following the determination of the 2025 NHL Draft lottery results), Montreal shall receive Florida's 2025 first (1st) round choice).
If Florida's 2025 First Round Choice DOES NOT Transfer to Calgary (pursuant to the conditions on an earlier trade)

3. In the event the conditions to trigger Montreal's option as noted in #1 above does not occur, or Montreal declines to exercise this option, the following conditions shall prevail:

A. If Calgary's own 2025 first (1st) round choice is not in the top-10 selections of the 2025 NHL Draft (following the determination of the 2025 NHL Draft lottery results), Montreal shall receive Calgary's own 2025 first (1st) round choice, and additionally,

1) If Florida's own 2025 first (1st) round choice is not in the top-10 selections of the 2025 NHL Draft (following the determination of the 2025 NHL Draft lottery results); and,
2) Florida's 2025 first (1st) round choice has been transferred to another NHL Club; and,
3) Florida's 2025 first round draft position is better than Calgary's 2025 first round draft position; then Calgary will transfer their own 2025 fourth round choice to Montreal.
B. If Calgary's own 2025 first (1st) round choice is a top-10 selection (following the determination of the 2025 NHL Draft lottery results), Montreal shall receive Calgary's 2025 first (1st) round choice, subject to the following condition below:

1) In the event Calgary's 2025 first (1st) round choice is the first (1st) selection overall in the 2025 NHL Draft (following the determination of the 2025 NHL Draft lottery results), Calgary will retain its own 2025 first (1st) round choice and Montreal shall instead receive Calgary's own 2025 third (3rd) round choice and a conditional 2026 first (1st) round choice. Montreal shall receive the better of Calgary's 2026 first (1st) round choice or Florida's 2026 first (1st) round choice (following the determination of the 2026 NHL Draft lottery results) (previously conditionally acquired by Calgary)."

Tl;dr

Kent Hughes and Brad Treliving lawyered the absolute hell out of this trade, borderline overboard, and luckily the NHL employs accountants who can keep track of all those conditions and sub-provisions.

Basically, it depends on the outcome of Florida's 1st, acquired in the Matthew Tkachuk trade, and banks on the inevitable decline of the Calgary Flames. Very wise move by Canadiens' GM Kent Hughes, who decided that he wants the highest possible 1st, so if Florida or Calgary end up with late first rounders, he doesn't want it. And the Flames' competitive window is definitely open, but its longevity is in question:

Therefore, Hughes is anticipating Calgary's future first rounders being higher picks than their upcoming ones. That is next-level strategizing.