You win by signing him in the 9's and supplement as the cap goes up. Just don't make foolish signings that hamper your ability to ice a good lineup and paying a star does not hamper you.

people i think forget how negotiations work. he asks for 10, leafs offer less, they meet somewhere close to the middle, he signs in between 8.8 and 9.5. problem solved

No way the Wild can afford Brodie.

I heard somewhere, may have been on the radio, that apparently cgy doesnt want conroy dealing with treliving, not sure how true that is

Good point. Personally, I wouldn't want to go above 8.5 Anything in the 9's seems crazy to me

I think you're using the wrong DeBrincat trade, though - Nylander has this year left at $6.9M before needing a new deal - just like Cat had last season left at $6.4M. I'd argue that the original package Ottawa sent is the value the Leafs should be trying to get.

To answer the question your title poses, though? You win the Nylander situation by keeping him. The team is constructed to be a Cup contender this year with a ton of expiring contracts, and any trade for Nylander is going to be the equivalent of trading a dollar bill for a handful of change. If he walks this summer, sure it sucks not maximizing him, but I'd argue that nothing you're going to bring into town in a Nylander trade is going to add as much as value to the team for this season as simply keeping Willie around would.

I have heard that too. I think he was cut off by the organization

8.5 is too low. Ideally for me it would be the meier contract at 8.8 but i beleive nylander is slightly better and has more leverage, im ok wth 9.5 because if leafs can pay reaves an extra 300k they can pay willy an extra 700k

The original trade makes sense. I'd just add that you can't let a talent like Nylander walk for nothing.

Borgen is a 15 minute a night defenseman. He's a third pairing guy. Make the trade for oleksiak and ditch the fourth.

And stop trading the Leafs best defensive defenseman