this wouldn't have been the Hawks prime. they didn't have Hossa yet this year. they were already getting very good (which is why Hoss went there) but they were not quite in their prime yet.
I thought long and hard about this for years Prime Hawks and Penguins probably would have been 2014 Crosby, Malkin, Toews, Kane all would have all been in their mid to late 20’s. Both teams in 2014 were serious cup contenders but neither of them won. But it would turn out that both duos still had deep cup runs in them. But as far as the best matchup probably would have been 2010 Blackhawks vs the 2017 Penguins (2013 Hawks may have been better as far as accomplishments and chemistry and also a more playoff experienced core but we didn’t see them play a full 82 games and on paper the 2010 Hawks were stacked and more dominant in the playoffs) (2017 Penguins had a better supporting cast than 08, 09, 16, Penguins with the addition of Kessel and Guentzel *2016 team didn’t have Guentzel. And 2017 Penguins had a more grizzled Crosby and Malkin at the tail end of their prime) If I can make 1 retcon to both teams in would be goaltending. For Chicago swap Antti Neimi for Corey Crawford and for Pittsburgh swap Matt Murray for Marc-Andre Fleury. Boom… Greatest matchup of the generation. _____ in 7