Quoting: Twins1568
Tkachuk is worth more than Nylander, Lindholm 1v1 Nylander would be a huge upgrade for Toronto IMO
Not because of skills, but what Lindholm brings as a 200 feet player.
What, exactly?
They're both pretty good at corsi, PK, takeaways, and faceoffs. Lindholm hits more in a season than Nylander has in his career, but that's still not saying much. The bigger differences are in age and consistent offense.
Nylander has three seasons of at least 20 goals and 45 points. Tkachuk has three. Lindholm has one. Lindholm doesn't belong in this conversation, unless the Flames also throw in a 1LW, with enough retention to make the cap work. If Toronto thinks about trading one of their big four, it's probably to add a 1LW or a #1RD, not just to come up with something that helps some other team, and seems fair to fans on the internet. They like Nylander, in Toronto.
Obviously Tkachuk is younger and tougher and meaner, and that all has value. But how much? Nylander+late 1st+Liljegren=Tkachuk? Tkachuk, Matthews, and Marner could be a great 1st line for a long time, but it would take that kind of an overpay to move a fan favorite out of Calgary, and even if Toronto pays that much, who do the Flames move to LW?
Assuming the flames don't want to move Tkachuk, but they want to make an offer that gets Toronto to think about moving Nylander, here's a more realistic idea:
Nylander+Kerfoot (to mostly balance the cap)=Lindholm+Gaudreau(retained 1 or 2M, to balance the cap the rest of the way)+2nd. That gives Toronto the proven top-six LW they've been missing since JVR left, and only slightly downgrades them at 2RW. I think that gets the Leafs on the phone, without including Tkachuk. It gives Calgary a top line of either Tkachuk, Monahan, and Nylander, or they can move Nylander to center and play Tkachuk, Nylander, and Mangiapane together, to go young, for a 1st line that lasts a long, long time. Toronto can play Gaudreau with Matthews and Marner, and hope that Lindholm and Tavares do well enough together, or they can move Lindholm to 3C for a great two-way third line, and see who else breaks out on Tavares' wing. Maybe even get away with Boyd or Spezza up there, as a rental, while a long term option develops.