TRUTH!
Chiarelli and early-Holland really did a number. Chia gutted the club of all wingers for Drai and McDavid, leading to years of them playing with Puljujarvi and Yamamoto (both currently out of the NHL), while Holland somehow wound up (after two seasons) with only Nurse and Larsson as viable NHL defencemen. He gave up like a farm-girl on prom-night to Nurse's agent in 2020, getting taken to the cleaners and overpaying by about $4-5 million per season what Nurse was really worth. Then he somehow isolated Larsson or let him wait too long (see: Broberg, Holloway), and lost him later on.
The org's (and Dave Tippet's) unhealthy attachment to Mike Smith apparently led the org to think they didn't need to worry about goaltending... And why would you, when you've attached your sails to a 40-year-old who'd never won anything? This lack of goaltending priority in turn has led to the current best goalie on the club (who just gave up 5 to Seattle) being a career AHL-er who couldn't make the 2020 or 2021 Red Wings (two of the worst teams of all time). In between these disasters was the $10 million of cap money they paid to Jack Campbell to play in the AHL.
Then, Holland's exit strategy was (as is his wont) to prioritize aging vets over up-and-comers, so he let Broberg and Holloway sit and wait... and wait.... The org in general managed to double-down on this error by having NO GM at all during the summer period, leaving the unsigned players ripe for offer sheets that duly stripped our roster of the only two important young(er) players we had.
NHL scoring since Dec. 23rd, 2024:
8. Sidney Crosby -- 45 points (-17)
13. Dylan Holloway -- 43 points (+17)
19. Connor McDavid -- 41 points (-1)
Yep.