At that cap hit, it could make sense to run a cheap tandem, but all that retention should cost them so much it isn't worth it.
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Ottawa looks better off buying him out this offseason or the next, so for them to retain in a trade seams like it'd cost some, plus the third party retention.
Watching them both I'd say Jack has the greater upside tbh. Murray wasn't that great in Pittsburgh but was surprisingly very stable & consistent behind a strong team to win 2 cups; fleury was so inconsistent & unreliable at times that average (but consistent) joe was all they needed.
but watching him since I don't really know what to think about him.
If they can somehow get him closer to 25% of his 6.25m cap hit, great; they can form a cheap tandem and improve the team in front of them, you can win a cup that way. I just think it's so unlikely they could do this without giving up too many assets, unless he's bought out or Doiron & another GM make pretty bad deals to help the Leafs.