This article examines the articulation of the Black ghetto to authenticity through the involvement of hip hop star Jay-Z in two highly publicized basketball-related ventures during 2003. During that year, Jay-Z organized a team for the Entertainer’s Basketball Classic (EBC) in Harlem’s Rucker Park and joined a team of investors aiming to move the New Jersey Nets to a new arena in Brooklyn. Informed by cultural studies scholarship, the paper explains the context through which basketball and hip hop were articulated with authenticity, and were deployed towards the goal of managing a career transition for Jay-Z, and was also used to gain public support for a controversial proposal to build an arena in the Atlantic Yards area of Brooklyn.