I simply don`t understand the logic of this trade as it feels like a shoe horn fit.

Looking at from both sides:
What does Toronto need? Goalie & Maybe a upgraded on Defence.
So you trade for Bo Horvat (F) & Tyler Myers (D)?
While only giving up Alex Keerfoot (F) & Justin Holl (D) while throwing in a 3rd to have Vancouver retain $3M of Myers contract to make this work.

Vancouver:
How does trading Bo Harvat for Alex Keerfoot make your team better?
How does Trading a slow Tyler Myers for Justin Holl make your team better? Answer to this one is salary dump and slightly young player that you have no intentions of resigning at the end of the year. Which you hope to flip for more picks at the deadline. But I am not retaining if that is the situation.

Okay, More I think about the Myers for Holl aspect of the trade works if Vancouver receives 3rd round pick and retains a lot less then 50% of Myers contract. But this doesn`t really work from a Toronto aspect then does it.

Horvat >>>>>>>>>>> Kerfoot and a 3rd

Myers at 50% >>> Holl

The first part is right, the second part soooo soooo wrong. I wouldn't trade Holl straight up for Myers at 50%. 3 years at 3M is still over priced

Myers yes, with Horvat, hell no

We don't need a goalie. Samsonov has been excellent, and I think he'll carry on that way provided he stays healthy.
We may need an upgrade on D, but with Sandin and Liljgren playing well, I'm much more comfortable with our D. I'm not even scared of Holl as the #6.
We need another top 6 guy and Horvat is a perfect fit. We also need a little more Jam in our bottom 6.

Think of it as a counter offer response to this https://www.capfriendly.com/trade-machine/18162

The point being it would take something like this to get Toronto (or any contending team for that matter) to take on Myers even with 50% retention.

I think this is probably a bit generous with horvat included but an interesting idea.

For the leafs I would rather see them aquire tucker poolman(if healthy) and Collin Delia from Vancouver.

Poolman gives them a defensive minded RD who can play in top4 comfortably and Delia would be a more experienced backup option.

Probably a bit, I thought about making it a 2nd instead of a 3rd or if Horvat came with retention too making it a 1st or a good prospect. In the end I decided to just keep it simple and made it a 3rd.

Regarding Myers the Leafs could use a bigger more physical defenseman than Holl and Myers is that. Mind you he's slow, isn't very good, is highly overpaid and has another year left on his contract after this one so it'd take quite a bit for a contending team to take on his contract even at 50% retained.

What the **** even is this trade?

My Gran with dementia wouldn't even make this