I think Backes is owed 5 mil over 2 seasons if he's moved after Jul 1st, and that's for a 6m cap hit

Toronto isn't trading Horton, as he just sits on LTIR and doesn't hurt their cap space.

After July 1st Zaitsev is owed less than 20 million real dollars for the next 5 years. And if you buy him out in 2022 (when you are assuming to be competitive) it's not too big of a hit. If the hope is to just hit the floor, competitive team be damned, he's a guy that helps. Now I would assume Ottawa would want a lot for helping Toronto to get out of that deal. Is it worth Kapanen, probably not, but potentially a young AHL guy right now and/or a draft pick is the right price to pay.

Toronto could even take the Gaborik and McArthur contracts back in kind. To hit the floor, Ottawa needs them to stay on the active roster. But if they are on the active roster, insurance does not pay the 80% of their contract cost, so they're expensive to Melnyk. There's about 11 mil owed to the two of them for the next 2 years, so the actual financial savings over that time is pretty close. I could see Ottawa doing some math and trying to figure out if it's worth it for them.

Plus, Ottawa just hired the Leafs assistant who played Zaitsev a ton of the penalty kill, so he'd be fine abusing Z's icetime while he shelters prospects and players in the organizations longterm future.

Well to be honest the trade proposed isn't really taking much of value. Some might trade Kral + 3rd for Beaudin (although unlikely in my opinion). But yeah, don't see Ottawa wanting to take it because of the real dollar value. A more likely scenario would be them taking on the Marleau contract.

He has a NMC and I doubt very much he is waiving it to spend his last season losing 40-50 games in Ottawa.

He could be Orpiked, and I don't say that lightly. There has to be a clear benifit to all sides for it to be accepted by the league and by Marleau.

To TOR: Condon
To OTT: Marleau + Sparks

Toronto saves $3M after resigning Marleau for a $1M
Ottawa gains $3.85M ($6.25M-$2.4M) towards their cap while saving $2.16M (Condon salary - buyout cost)
Marleau gains $583K

I would argue Horton's contract will become an issue if Toronto has issues signing players RFA's before they make trades. (Ex trying to sign Kapanen before they can trade Nylander or whoever) Horton's money will restrict how much TO can spend before they trade someone. If they don't have the room to sign Johnsson, Kapanen, or Marner before they trade someone they are really putting themselves in a bind when this is a relatively cheap way to avoid that situation.

I do agree Zaitsev may interest the sens because of Smith but with that many years left how good of a prospect/pick do you feel is acceptable to add in? Then who are your 3 D on the right side?

In regards to the Marleau/Orpik corollary I thought the league closed that loophole. It's certainly an option if allowed. I'm also pretty sure you're allowed to use LTIR in the summer and exceed the cap in the summer as well (at least 10%).

I think Z makes a bit of sense for Ottawa because of what I mentioned above, and can be bought out in 2022 pretty easily. You are right in that the big issue with trading him is replacing him on the RS of the Leafs D. I think you try to swing a trade using Kapanen or AJ to get a guy like Colin Miller if you've traded Zaitsev. Then maybe try to sign a short-term stopgap like Adam McQuaid or Anton Stralman until the AHL guys are ready. That leaves you with:

Rielly/Miller
Muzzin/Dermott
Rosen/McQuaid(Stralman)

That D you can win with.