They wouldn't in reality, nor would I expect a 2 X Exec of the year GM to make such a move.
However, if you're trading Marner (as 1 of the 3 players in this poll), because of his massive contract, you could see how cap management could be so much better by investing it in more players to build a team around and also higher priority ones like a #1C and #1G instead of a #1winger for what you're currently investing that much cap % in.
So my decision was based on picking the 3 worst Leafs worst contracts. It would be Marner for overpaid contract, Mrazek for overpaid and bad contract, and Holl $2 mil for just be bad overall and needs to go, particularly after than embarasing protecting him the expansion draft and let Seattle have their 27 goal and team leading scorer McCann instead for nearly the same cap $2.9 mil.
PS. Tavares NMC is unmovable, so picking him wouldn't be any more realistic then the point I was attempting to make.