Fire Shanahan and Dubas day one and bring in a President and GM with experience.
Instruct the new GM to dismantle the core forwards(except Nylander) while resigning Reilly for 5x9.75 or something similar, hopefully not for more than five years. Not that I like him that much but he seems to be more genuine than the rest and we need to hit the cap floor - not to mention we really have no d prospects that have a hope of being top pair d so he's not gonna be in the way. The instructions for dismantling the core would be specific - we must obtain at least one roster player between 22 and 25 and at least one pick and at least one prospect. Minimum two right handed defenseman and two centers coming back in total for Matthews+Tavares+Marner. Retain on Tavares as needed. The players brought in will at minimum have 125 games played, decent potential for growth, skate well and play hard. No perimeter players. Also on the chopping block would be Muzzin, Holl, Dermott, Engval and Micheyev. Might get something decent in return for these five. Emphasis on center prospects.
This will change the culture of the team over night.
Run a forward group of Nylander, Kerfoot, Kase, Bunting, Kampf, Spezza, Simmonds, Ritchie and Amadio plus the new players brought in.
Run a defense of Reilly, Brodie, Sandin and Liljegren plus the new players brought in.