Both teams decline. No one is going to hand the Leafs multiple picks for cap dumps.

For Ritchie, I understand. But Holl has been a legitimate top 4 defenseman in the past, so there could be teams like Nashville or Chicago that could make use of him.

Tbh I just don't think the Leafs will be able to go with two 3+ million dollar goalies with their cap structure. Some of the cap could be used to get a number 4 defenceman.

Legitimate top 4 is a bit of a stretch to me. Even in his prime I never thought of Holl as much more than a fringe #4. Regardless, NSH's top 4 is locked down for the foreseeable future. Hopefully the team is ready to move on from filling out the bottom pair with overpaid vets like Borowiecki next season. I can't see any reason for NSH to be interested in Holl.

I guess Holl couldn't make CHI's backend any worse, but would they bother doing a trade like that either? It feels like a rearranging the deck chairs on the Titanic move. Their D core is already getting up there in age - you think they'd want to inject some youth instead of a 30 year old.