Digging through the crates of sneaker archives for this week’s Flight School, we stumbled upon the Reebok S. Carter, a boundary-breaking and well-hyped sneaker by Jay Z. To take you down memory lane, the S. Carter marked the first time Reebok made a shoe endorsed by an entertainer. The terms of the deal were loose as Jay Z didn’t need to wear Reebok all the time and the design of the sneaker was very similar to a certain Gucci tennis shoe. It sounds odd to say that these dropped a decade ago as it feels like yesterday but that might be large-in-part of Jay Z consistently being the innovative artist creating #newrules.