We should've had multiple cups before Jackson was even in the picture. We blew our best shot prior to him taking over, and it was only because mcdrai went completely supernova. It's not like the makeup of the team was that good.
This singular offseason is not the defining moment if we do fail to get a cup. It's the 10 years prior. The 10 years of refusing to address particular needs, 10 years later still needing a top 4 dman and bonafide starting tendy, 10 years of failed drafting impact 1st round fwds and top 6 talent (yams, JP, bourgault...etc), 10 years of deliberately cucking our young star players (Holloway, Broberg, letting Bouchard rot for 2 years and resiging barrie for no reason), 10 years of barely any impact players drafted outside of the 1st round. 10 years of almost no homegrown players to solidify roster spots. 10 years of failing to get competent top 6 wingers outside of Hyman.
I could keep going on. Yes, this offseason was an unmitigated disaster, but we've likely already blew our best shot to win a cup. I refuse to believe Dylan Holloway is the singular reason we aren't winning a cup. McLeod was a non-factor in the playoffs. Broberg has been replaced by Walman. It's all of the brain dead decisions our incompetent front office (empowered by incompetent ownership) has done since we drafted McD, and now we are stuck with this group for the foreseeable future.