Kind of a tough call. It really requires a team with good but not elite talent on the way out due to age starting out by establishing a trend of really poor front office decisions (such as from a GM who's poor but getting lots of slack, or a meddling owner, or whatever). Then one has to couple that with several drafts going really poorly, and a few Inexplicable Trades that go even worse.
The closest we've gotten to seeing that latter show up recently was Minnesota, but they quickly amputated so the patient may have been saved. Montreal might have been a candidate, except the Domi trade actually worked. Pittsburgh under Rutherford have had some dubious-looking moments in the market lately, but they've got too many elite guys for things to go south. Dallas just picked up Heiskanen, so they may still have hope. Half the PHWA have already printed their eulogies for Columbus, but the Jackets are doing too well in the draft and still have too many good young players despite high-profile departures. Similar considerations exist for Winnipeg. And so on.
My best guess, if I had a gun to my head and had to pick one team? Detroit. I just think the rebuild will take a long time, even with Stevie Y present. But I would not be at all shocked if they end up making that pick look dumb in short order. There's just too many variables. It takes a strange sort of talented incompetence to be that hopeless.