I've long said that Gaudreau's value is probably relatively stable whether he's traded now or at this final TDL based on the ED and his NTC. I thought last TDL might have been the time to get a bit more for him, and that it didn't necessarily preclude the Flames from being competitive in the playoffs, but I digress.
I still think sooner is better on the basis of the future assets involved coming to fruition for this team's new window (Tkachuk/Valimaki/Andersson/Dube/Mangi), but I think there is one other possible scenario: extend him at the first possible opportunity (Jul-1-2021 equivalent) and then trade him if so desired. You're still limited to his NTC
2022 free agency class has potential to be crazy (though I think most re-sign, there could still be a few huge fish). It's simple risk mitigation for both sides. You tend to save a few bucks on AAV by committing early, but there is a lot of value for a player to avoid the stress/uncertainty that comes with playing out the stretch towards UFA status.
I don't think it's very likely, but it's worth considering as an outside chance. I don't think an FMV extension increases JG's trade value by very much, but it takes the doomsday clock out of the picture.
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