Well, the Hawks did sign Hossa to a huge contract to put them over the top earlier in the decade, and one could argue it worked. 3 Cups in 5 years will give their fans some pretty good memories.
Of course, back then, Toews and Kane were great youngsters and Seabrook and Keith were at their NHL peak (which always seems to be around 27 years old). Still good players, but besides Saad, it seems with all those major contracts, they are only able to fill in journeymen around these core guys.
It probably depends on how long it takes them to rebuild. The NY Rangers pulled out all the stops to win a Stanley Cup in 1994, and it took them almost 15 years to really recover from that. There were 25 players from that team whose names were etched on the Stanley Cup, and the Rangers only drafted five of them. They gave up some very talented players (Mike Gartner, Doug Weight, Tony Amonte, James Patrick, John Vanbiesbrouck, Bernie Nicholls, etc.) to assemble that team, and the loss of younger players like Weight and Amonte really left them old and slow almost immediately after they won.