"Kane wants to play with Sid"

*places him on the third line with Gaudreau and McGinn*

Not a chance the Hawks accept that. Dumoulin is a cap dump period. Pit can not place value on him under the assumption the other team that they will retain half and flip the cap dump for value...that's not how trades work. Furthermore, the Hawks will not have a retention spot to flip Dumoulin.

Now, understanding that Dumoulin is negative value and removing that from the trade, there is not a chance the Hawks accept just a late 1st for Kane either and with Dumoulin the trade value is even less to the Hawks. Pit would have to include their best prospect or another 1st rounder if they want Kane at 50% retention plus taking on Dumoulin's cap hit.

I think that Hawks can get much much better for Kane, so they say no.

The Gaudreau trade would be a slap in the face. Hextall could've resigned him to the pens in 21 and choose not to, so sending Kap and a 2nd would just be a terrible look imo for management.

Why would MTL want Heinen ?

If Kane won't waive for any but a small number of teams I'd take a deal like this. If he is open to moving without too many restrictions I think CHI may get a better offer.