I've actually drawn up something exactly like this attaining Sheary. I just don't see Dubas parting ways with Kerfoot before Engvall. Kerfoot is more versatile and closer with the team off the ice.

i would accept that

Don't think Caps do that. Sheary brings basically the same thing as Kerfoot as a much cheaper price.

As a Leafs fan and a Caps fan, I love this trade for both side. I'm gonna try to add in my thoughts as both a Leafs and Caps fan.

Here's my Caps fan take: uhhh we like Conor quite a bit. He's a fan favorite here. But, shifting away from fan bias and to logic and reason: as weird as it sounds, I do think Toronto may need to throw in a mid-draft pick. Sheary's a really versatile player, and his lower cap hit definitely adds value. Sheary's a player who may not have the two-way talent of Kerfoot, but he's a hard worker who always is adding value to the play and is a really underappreciated offensive presence. He's never invisible. And invisibility is a big problem with Kerfoot; when he's there, he's good, but he's often just not making an impact. But honestly, I think Kerfoot may be more of a fit on the Caps. We need a player like him that is conscientious (had to google how to spell that one) defensively and can help on the PK, since our defensive strategy beyond our 'shutdown fourth line' which doesn't shut much down and Fehervary and Jensen trying to cover for Carlson and Orlov being forwards in disguise is just 'shrug'. Kerfoot would help fix that in a major way. But that said, with their cap hits, I think Toronto would need to add, here.

Here's my Leafs fan take: nooo I like Kerfoot. Okay, shifting to logic and reason. I... uh... I think Toronto needs to throw in a pick, here. This would be the golden solution to our cap problems, and not only that, but we'd get a guy who could thrive on the third line and could maybe even be tested out in the top six. I think Sheary's a really underrated player who, again, is a hard worker that can do things that Toronto could really use. Plus, he's an ever-present force when he's on the ice. My best comparison for Sheary might be a better version of Kase. So we'd get a player that could maybe be even more of a fit than Kerfoot and solve our cap problems, two birds with one stone.

Also, I would be shocked if Sheary sniffs the Caps fourth line. He's a third line lock, but especially with people out, I'd slot him on the second line alongside Strome and Mantha/Brown.

So my final, all together take: love this for both sides. Toronto would need to add a fourth, though.

Value is probably fine here, but the point of moving Sheary would be to open up a roster spot for one of the younger guys who really impressed in camp like Snively or Protas. Sheary may be playing on the fourth line to begin the season, but if they made this trade they would then almost certainly just play Kerfoot on the fourth line in his place. I think moving Sheary makes some sense for the Caps, and getting him makes sense for the Leafs, but the Kerfoot part doesn't really.