This chapter concludes Media Building by returning to the fate of a familiar media edifice: the Chicago Tribune Tower. The repurposing of the iconic Tribune Tower is emblematic of the creative challenges faced by traditional news organizations in the wake of rapid transformation of the media ecosystem over the few decades. The neo-Gothic structure, now reflecting the former newspaper headquarters in name only, is promoted as a shining example of adaptive reuse for luxury condominium residences. Looking back to European cathedrals for architectural inspiration while quickly embracing new media technologies to stay competitive, the Tower was, from its completion in 1925, a contradiction in form and function. By the turn of the twenty-first century, it became an unsustainable balancing act, which has been the fate of other media buildings not so fortunate to be salvaged. Questions remain whether the legacy media can adapt as quickly to new owners who may value such distinctive property over any of their news products.