Not that I'm advocating for it right now, but a reasonable line of thinking says that if your only goal is to win a Stanley Cup, and you can't sign your core players to favorable/fair long term contracts (either due to cap mismanagement or the player being unwilling), then they should be dealt at some point, perhaps during their bridge deal.
This league is all about benefitting from good contracts, and Benning has put himself in a situation where he can't afford term, so it's very difficult to see what window they're actually targeting for a Cup. Is it a win now team? Because they were awful last year and the defense looks shaky at best. Is it a win in 3 years team? Because key players will have moved on/degrade/be on much more expensive deals. This was the issue with the Miller deal - from a pick value and player performance perspective it was a big win for Benning, but from a team perspective, it was a premature move for a team that was still in the early stages of a rebuild.