The Debrincat trade was a marketing move to prep the team for the sale. I don't think it was the right move on the ice, but I am willing to give them a pass on it because of the external factors.
Remember how fans on Reddit and Twitter were excited about the team and proclaimed it the "Summer Of Pierre"? That's the kind of mentality and hype that they needed in the marketplace. They needed an increase in season ticket sales, fan interest, etc.
Chychrun, Korpisalo, Tarasenko, etc - those were Dorion trying to win now and save his job. He offered Tarasenko and Korpisalo both way more term than any other team, because the term would be the problem of the next GM. Dorion was auditioning for a job, both here or somewhere else.
With that said, I don't think Chychrun was the worst gamble, because the team was in contention for a playoff spot at the time they made the trade.
Because of how funky the standings were, there was a reasonable shot they could have made the playoffs, and that pick ends up in the 17+ range. Not only that, Chychrun had term so they could recoup the 1st down the line.
I understand that it isn't the Chychrun trade in isolation, it is the amount of similar trades and moves they made over the entire rebuild that resulted in the team giving up an astounding amount of draft picks with very little to show for it.