The 2010 BP Deepwater Horizon blowout spill in the Gulf of Mexico shocked the nation with the amount of oil and harm it unleashed upon the Gulf and its natural and human ecosystems. As details of the calamity became available, they revealed frustrating parallels to the 1989 Exxon Valdez oil spill in the Gulf of Alaska in terms of causation and impaired response capability. Similar systemic deficits characterized the actions of corporate managers and state and federal regulators in the oil industry of both Gulfs. In a “di-polar” system where industry and government regulators come too close together, responsible overall management of operations and risks suffers. The lessons and recommendations incorporated in the 1990 Alaska Oil Spill Commission’s Final Report on the Exxon Valdez spill, including watchdog citizen councils, were highly germane but largely ignored or forgotten in the decades between the Alaska Report’s release and the 2010 BP tragedy. This Article reviews the Gulf of Mexico spill in light of the Gulf of Alaska spill, and notes how this time around we must finally learn how to deal more seriously with the mega-risks posed when di-polar convergences occur in these megasystems of hydrocarbon production and transport.