James Jebbia brought a lot of insight to Supreme via his involvement with Union. The branding and retail incorporated/ripped off strategic choices and aesthetics from luxury goods and fine art. To have your core product, the box logo tee, crib from an artist (Barbara Krueger) concerned with the dehumanizing aspects of capitalism points to a savvy, diabolical outlook, as do all the collaborations. You see Joy Division Unknown Pleasures tees everywhere, but only Supreme licensed the art from Peter Saville.
They've always played with exclusivity as a calling card, so the rude employees, limited drops, and long lines are strategic. Supreme wants to make you feel like an outsider and desire to be a part of their thing, although you most certainly never will. But you can wear the shirt: manipulation through class anxiety.
The recent videos and skate team really bought them a lot more time. They injected a lot of energy. And if they diversify, they could last longer. Look at Polo/RRL - a brand can grow with its customers.