Leafs 2019-20 Trading Nylander for a right defense whatever non-roster assets

Or how about just keep Nylander because Liljegren will be ready to play in the next year or two. Then you have Nylander, an incredibly skilled winger with Patrick Kane like hands and unreal skating, edges and puck control ability. Also got Liljegren who can do much of the same as Faulk. Great hands, skating, ability to quarterback the PP etc. and has an even higher ceiling on a cheaper contract.

The problem in keeping Nylander too much money is spent on the forwards and the cap issues are just going to continue with a weaker defense. See my previous teams. I agree Liljegren will be very good but will he be ready next year. He will be part of the future for sure.

I think the problem is that the cap for defensive players is spending 4.5 on Zaitsev and Faulk who aren't really good. That's over 9m you could sign an impact player for.
Also Nylander making 7 isn't half as big of a problem as Marleau making over 6. Without that contract, if you could hypotetically flip Zaitsev, you'd be able to sign freaking Karlsson - an actual difference-maker

Marner won't sign for 9 ... he'll demand 10-11 per ... and will likely be offer sheeted ... Nylander wasn't worth it (compensation picks), but Marner will be for a few teams with cap space who can offer 12M per
Karlsson will also be in the 10M+ range

It all depends on what Marner wants. Is he just in it for the money? Does he like being a leaf and playing with these team mates? Will any other team he would go to have a better chance of winning a cup if that is what is most important to him? Remember that he still will have a free agency big contract to come in the future. Who knows what he is thinking. Tavares left money on the table to sign with the leafs. Kadri signed at a discount to stay a leaf long term. And if the leafs sign him before July 1 then the potential of an offer sheet is gone.