In November of 2007, the Association of Southeast Asian Nations (ASEAN) celebrated its fortieth birthday at a gathering of the organization’s ten member states in Singapore. It was a celebration eclipsed by news of the military junta’s brutal repression of protests in Burma, an ASEAN member. The task of plotting a way forward for ASEAN has been punctuated by this and other improbable events, such as the March 2008 electoral losses of Malaysia’s ruling coalition and the catastrophic upheaval unleashed by Cyclone Nargis in Burma. Yet these “black swans” have unexpectedly produced opportunity for reform and democratization in the region.