Quoting: WN88
GM Craig Conroy would be immediately fired if he passed. Let's see: 33/34 year old Chris Tanev for 1 season, 34 year old Mikael Backlund for 1 season, and an undersized middle-six forward all for a top-10 40 goal scoring winger that comes with an 8 year extension. If those players were Leafs, other fans would say it costs the first just to dump those contracts. And ironically enough, given the Leafs cap situation, it probably would.
The only reason the flames would want Nylander is if Lindholm is staying. If he does stay, then Calgary is paying him roughly 8.75MM AAV, plus Nylander's 9.25MM AAV next year with a 4MM cap increase. That leaves $17,450,000 to fill 10 roster spots. Assuming Pelletier, Dube, Kylington, Zadorov and Wolf continue their trajectories, they all need raises, which will be over the average 1.745MM for each roster spot left. Thus, they'd be filling next year's roster with ELCs. Also that Florida pick is conditional and tied to the trade they made with Montreal to dump Monahan's contract. It costs them an additional 4th if they trade it and removes the protection they have by allowing Montreal to take Florida's pick. So trading that pick exposes them to losing a high draft pick in 2025 (assuming they continue to suck).
For this year, Calgary would only have 2.324MM in cap space left to find two bottom 6 centers, a top 4 RD, and a replacement for Hanifin. Assuming they can actually get a decent return for Hanfin, some of it would need to be allocated to fill the holes in the roster.
So no, Connie wouldn't be a fool to reject the deal. For what it's worth, I do think Backlund and Tanev would push the leaf's over the top. They are two of the best shut down players in the league.