But Dorion rather than seeing the best young team he could leave, succumbed apparently to players demanding he trade 1st rounders because they were ready now and to stop the rebuilding. I’d rather he left us more like Arizona did for Utah. But I guess his incentives weren’t to do that unfortunately.
If you ask me, this is the exact moment the rebuild went off the rails. Prior to this things were going somewhat decently - they had amassed some talent, had a small smattering of vets [Brown, Paul, Watson, Holden], and still had all of their picks to continue building. The vibes were immaculate.
...and then Tkachuk and Chabot show up at their exit interviews making demands like they're Connor McDavid or something. Now - Pierre Dorion has to take responsibility for run of ill-advised transactions that occurred in the wake of this event, but it's easy to see why it was done.
I think this is an area where the Senators were hurt by not having respected execs/advisors on staff. People that have respect in the hockey world and would have stood up to the impatient kids and said 'no. You aren't ready, and the team isn't ready'.
A few weeks ago I was listening to a podcast where Pierre McGuire was the guest, and he said that in most failed rebuilds you can look back and see a sort of 'watershed' moment where teams abandon their original vision and go off course. I think for the Senators that is clearly the Alex DeBrincat trade, and things just spiraled from there. McGuire also mentioned the importance of insulating your youth with quality veterans, and made reference to how much difficulty Ottawa had doing that. He specifically named Ryan Suter as a player they tried to sign in his one year as a Sens exec, but the guy just wasn't interested.
But here's the thing - even if the Sens had kept their picks in 2022 and 2023 the team on the ice isn't currently any better, and they've still got the Bradypocalypse [credit to frightenedinmate#2] looming over them. So I don't know how much changes. You're in a better position to rebuild again I guess.