Relative to our divisional rivals, except for Buffalo, our rebuild has been pretty ass.
Detroit's rebuild started when Yzerman was hired in 2019. Prior to that, Holland had depleted the organization of assets and had a shit ton of awful contracts on the roster with very few building blocks .Yzerman had to tear down a lot before he could even start building. He's done an adequate job accumulating assets, trying to fill the cupboards and drafting a few cornerstones (Seider, Raymond, etc.,) but not enough of his prospects have emerged as Ottawa's has which is why Detroit is 'behind' Ottawa. Even then, Detroit is still competitive and can make the playoffs despite not having as much elite talent as Ottawa. They've also never drafted higher than 4th as well during their rebuild relative to Ottawa who's had a 3rd, 4th, and 5th overall pick. They're only behind Ottawa because of draft luck.
MTL's rebuild pretty much started 3 years ago, but they had the luxury of having some pieces in the system (Suzuki, Caufield, Guhle, etc.,) before officially entering tank mode. Hughes also has a bigger wallet to play with, and they don't have to worry about actual player salaries when making any moves. 3 years after their rebuild, they have a legit chance at making the playoffs, so they've been ahead. Hughes has been a better GM in every tangible way.
Dorion set us back 2 years. We should have made the playoffs in the last two years but Dorion just has poor roster evaluation. The first rounders used for Cat and Chychrun could've been used on players that were better fits and we'd have made more progress than having two luxury type players that we didn't need. Aside from hitting well in some drafts, most of our asset management during our rebuild was Milbury level so it makes sense why its taken us nearly 8 years to make the playoffs.
To me a successful rebuild doesn't equal a cup, its building a roster that is regularly in the playoffs and can go deep. A cup isn't everything, long term success is and to me that's icing a team that is capable of making noise in the playoffs. Look at SJS under Armstrong. They didn't win a cup, but they had a decade winning hockey and were able to go deep several of the years they made the playoffs. The Leafs might be chokers, but their rebuild has been successful in the sense that they've iced rosters that have the talent to go deep, but sometimes it just takes years. Look at Washington, it took a decade+ to get the right pieces in to get Ovie a cup.
Our rebuild has been shite, but its because Dorion really approaches Milbury levels of being awful.