If he signs a deal CGY won’t do this but if he doesn’t then CGY might do it maybe

Would have to add in kyrou, thomas or perunovich to make calgary even consider this.

The Flames shouldn't be considering it all; Tkachuk is a bonfide top line winger with a unique skillset. But it's not exactly their choice. If they're in a position where they are trading him, it's because he's told them he's not signing an extension. And that gives Calgary very little leverage to demand a young player back in a trade, because Tkachuk is a year away from free agency when this contract is up. That puts Calgary on a clock to trade him (because they can't lose him for nothing) and if there's only a handful of teams that he's willing to sign an extension with, that reduces your market as well (see: Mark Stone trade to Vegas).

No but it also doesn't mean that St. Louis should be getting the best player in the deal at a considerable discount, especially if the likelihood of an extension is essentially guaranteed and the player going back to Alberta has already requested a trade from the Blues.

Tkachuk for Kyrou, Tarasenko, and a 1st at least makes more sense. I don't know why Calgary is giving up a pick in this case. I don't have much of a horse in this race but the deal as presented is far too in St. Louis' favour.

Not sure a player who is currently producing the same as Tkachuk and a first round pick is a "considerable" discount. I'm not defending the trade as currently constructed but Tarasenko is signed for as long as Tkachuk would be there if Calgary does nothing other than qualify him and he's being similarly productive right now. Tarasenko wants out, sure, but again if Calgary is trading Tkachuk then he wants out too. The Blues need to add in that scenario due to Tarasenko's age- a first round pick, maybe a prospect too. That's reasonable.

But they wouldn't give up Thomas or Kyrou as prospects for five years of Ryan O'Reilly, so there's no reason to believe they'll give them up as productive NHLers for a guy they can probably sign in free agency in a year regardless. Calgary needs to set their sights lower on someone like Kostin or Bolduc. Again, look at the Mark Stone trade, which was a very similar scenario to the one the Flames could find themselves in if Tkachuk is only willing to extend with a few teams. They got an A prospect, a second round pick, and a BC prospect for him. Not a lot for one of the best wingers in the game. If push comes to shove, Calgary has no leverage.