Happens that all of our superstars in the last two decades happened to peak or go close to over the hill in their careers just when Ottawa became lottery team material and wanted to rebuild. Re: Spezza/EK/Stone all in their 28-30 age where they've established themselves as legit players but teams out of playoffs/retooling.
Problem is we never seem to flip them for a good return that allows us to sustain a long period of success to keep a star around if they don't want to be here. Not that players dont' want to be here but we trade away the ones that do anyways (Turris, EK)
And then theres the problem with the owner.
Could also argue, we've had some reactionary/bad decision making to try and put us over the top.
Turris -> Duchene was supposed to make us legit, actually did opposite (possibly set us back).
Silfverberg -> Ryan was also supposed to make us contenders. That was kind of a lateral move with long term loss as Ryan became less effective 2-3 years down the road and Silf became a solid secondary player that can step up.
Zibanejad -> Brass I can't really complain about. That actually gave us a good run, but may be short sighted. Depends what you want but it's easy to complain while we're in a tire fire. Sure no one had anything negative to say while Brass was scoring 0.6 ppg in the playoffs on that magical run.
And then we had bad luck on some picks during other retool years a la Noesen, Puempel, Prince, Cowen that keep perpetuating our vicious cycle of low-lows followed with moderate highs.
Now, if we can keep drafting well, maybe flip guys that want to jump this sinking ship for decent futures and Tkachuk/Brown/Chabot/White/Batherson/Formenton/Lajoie actually pan out into Top liners, maybe this is a crop that we can sustain success with. But if we're going to lose Duchene/Stone/Ceci walk for nothing, considering we're possibly missing out on a top 10 pick this year, we're likely to run dry again in 5 years when some of the young crop resign elsewhere or we trade them at a loss.