I bet the league would take a very dim view of this as it would be a cap circumvention. The retaining portion of the CBA was to allow trades not let other teams just eat salary for high priced teams.

Do not think there is anything in CBA, to prohibit this but Bettman and league might penalize Leafs non the less.

Didn't the Coyotes trade for Hossa and Datsyuk for this same reason though?

Completely different scenario as the Coyotes kept both players in order to help reach the cap floor without actually paying salaries.

There's a few flaws in this scenario which, if I understand correctly...the Leafs are essentially paying the Coyotes two 3rd round draft picks in order to pay $3.125m of Marleau's contract for 1 year...

1. Marleau would need to waive his NMC
2. Arizona ownership would have to value two 3rd round picks more than shelling out $3.125m
3. It's not a legal move under the CBA. A team cannot reacquire a player they traded away for a period of one calendar year, if the trade sending the player back has salary retained in the deal.

Arizona has no reason to trade. They are above cap floor. Why do people think this is an issue?
And no the Datsyuk, Hossa, Bolland were not traded for the same reason as this . If I was the Leafs, and I could pull this trade for Arizona, I would not resign Marleau. That's the exact reason why Marleau doesn't agree to any of this nonsense. And signing Marleau for two years....geez, the Leafs are trying to rid themselves of contract.

why not just have a team buy him out after his signing bonus is paid. Yes 35+ contracts can be bought out, there is no cap relief, but there is salary relief. Other team effectively would pay 800K for whatever pick the leafs offer, in exchange for taking on marleaus cap hit for 1 year. Leafs can then resign him or another team, plus we know it's allowed because the league let it go last year for Orpik. There is no possible way they could stop it this year, maybe after a new CBA.

Win-win-win. Leafs get cap space, marleau gets more money when he resigns with a team, and other team gets a high pick for taking on cap space and only spending 800K.

edit. you do this on July 2, not mid 2018-2019 season.

In order to buy him out, they have to put him on waivers. In order to put him on waivers, Marleau must waive his NMC.

Even if he decided to do that, there would be 0 guarantees that he would pass thru waivers. 1 year for a 25+ goal scorer at $6.25m when it's proven he's a great locker-room leader/influence is not an undesirable player/contract...

so again...would Marleau ever waive his NMC and subject himself to having no control over where he may end up? Just not a realistic option.

There are a couple differences.

A. Both Datsyuk, for one year , Hossa for 2 or 3 years were or are on the Coyotes roster, yes they were brought into bring up the cap to the floor. But they were not returned to their original team that traded them to Arizona at half price. In your scenario you are using Arizona to eat half of Marleau's contract, and then trade back to Leafs. Both of they players are were or still on the Coyotes roster.

B. In Datysuk's case the cap hit was 7 million, but in dollars paid out it was zero, because he went back to Russia to play in KHL. So it looked like a 7 million dollar cap hit but in reality was no money out of pocket for Arizona. I believe in the Hossa contract, most of it is covered in Insurance, so again looks like cap dollars but very little out of pocket. What you are asking is for Arizona subsidize the Maple Leafs by paying over 3 million dollars to Marleau to play for them. That will cost you more than a 3rd round pick. And again i doubt the league will condone the move.

In Capfriendly's Buyout FAQ it states "If a player has a no-movement clause, the player can reject the option of waivers and proceed to the buyout process." So it would seem he has the ability to reject waivers and still get bought out, making this an effective solution.

Also I don't know if you can do a buyout outside of June 15th-31st? so the buyout team may be forced to eat his signing bonus