Pierre Dorion is taking a lot of heat for being Pierre Dorion.

If he brings back Erik Karlsson, perhaps an Alfredsson-involved management group would be grateful to him, and let him stay.

San Jose previously stated they would only retain 18 percent, but it is unlikely that any other team was putting up a 1 for 1 Subban for Weber type trade offer. Thomas Chabot is seen as a superstar defenseman. It doesn't matter if that is true or not. He's looked at as the guy who sometimes plays nearly 30 minutes a game. Having this kind of 26 year old defenseman made available to San Jose changes the complexion of the trade. Chabot and Karlsson are also redundant.

The trade could still be made with the rumoured 18 percent limit on retention, but the cap in/cap out retention looks better.

San Jose also might need to convince Chabot to stay. He would be unhappy about going to San Jose after spending his entire career in a rebuild. He may not want to go to San Jose. While he cannot block a trade, he can sulk and make it less fun to have him for the Sharks. It is possible that this deal would require a third team who would benefit from acquiring Chabot. In that case, Chabot has to be worth more in a trade than Karlsson, or Ottawa has to add. Or, there has to be stumbling blocks to moving Karlsson elsewhere (teams afraid of age+term) that there aren't with Chabot.

This would have to be considered. And yea flipping Chabot would be easier considering his age. But at 26 Chabot will still be in his prime in 3-4 years when sharks are a much stronger team with plenty of cap space to add impact players so I wouldn’t mind him being part of the rebuild.

I don't think the issue would be whether San Jose likes Chabot, more if Chabot is okay with going through another rebuild.

He arrived in Ottawa right when their rebuild started. So the scenario would be that he played through all those tough years and then is traded at the end of the rebuild to another team who is early in theirs. Of course, he doesn't have a NMC, but teams generally try to avoid acquiring players who don't want to play for them. So the more I think about it, the more likely it is that it would require a third party.