The express purpose of the NHL entry draft being ordered from worst teams to best is to help the bad teams get better.
I really think this needs some caveats.
On average, yes, we want to help bad teams get better. But bad teams need to do their own work too in addition to being handed all the best players.
- If a team fails year after year to convert the best prospects in the world to success, they deserve to stay bad for a while. There shouldn't be any guarantees for them. They're still going to get their 4ths and 5ths and 6ths but they need to do their own work.
- If a team rebuilds in a "good sportsmanship" way, they deserve some help. IMO that means they fight year after year aiming for the #16 spot with overachieving kids and a never-give-up attitude, but without the elite talent they need to put them over the edge. That team doesn't deserve the purgatory of being a bubble team forever. Once in a while we should throw them a bone, but again, with no guarantees.
Ideally, Chicago was not the "best" team to give a lottery pick to. But they were still worse than over half the league this year. Therefore they still need some help. Ideally it would have taken a few more years for that to happen but I think that's an acceptable cost of the randomness that makes the whole thing work.
I'm happy with my Red Wings getting 6ths for a while until one of two things happen. They overachieve and become a playoff team despite their bad lottery luck. Or they're set back for long enough that they finally get their lucky break and can adjust the rebuild from there. I don't want any guarantees, I just want the system to average out properly in the long run.