Nelson Mandela and other political prisoners from South Africa were imprisoned on notorious Robben Island from the mid-1960s until the end of the apartheid regime in 1991. The stark conditions and abusive treatment of these prisoners has been widely publicized. However, upon reflection and in retrospect, over the years, a type of metamorphosis occurred. Primarily drawing from firsthand accounts of the former prisoners and guards, it seems that Robben Island morphed from the traditional oppressive prison paradigm to one where the positively oriented prisoners disrupted the institution with a resulting climate of learning and transformation that eventually led to freedom and the end of apartheid. At a macro level of analysis, we use the theoretical lens of institutional work, and, at a micro level, positive psychological capital (hope, efficacy, resiliency, and optimism) to explain what happened. This metamorphosis led to one of, if not the greatest, societal transformations in modern history. We conclude by discussing some implications and lessons learned for organizational scholars and practitioners.