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In 2011, Obama authorized special operations forces to fly deep into Pakistani territory to find and eliminate Osama bin Laden. By all measures, it was a political and military success. Obama brought justice to the victims of 9/11 by relentlessly hunting down its mastermind. Then Vice-Admiral William McRaven executed an incredibly difficult covert action without losing a single American serviceman and with minimal collateral damage among residents of bin Laden’s compound. As a direct result of this operation, the national mood shifted at a time. At the same time, Obama began his reelection campaign. The need to look tough on terrorism while also fulfilling his promise to reduce the US military presence abroad left Obama with few choices and no good ones. As we will demonstrate, Obama clearly worried about incurring audience costs if he failed to fulfill his 2008 campaign promises about the wars. As a consequence, he declared the end of the War in Iraq and he claimed the 2009 Afghan surge had succeeded allowing him to start drawing down troops in both countries. Simultaneously, he increased the use of drones and began relying more heavily on Special Operations in Central and South Asia. All of these decisions had long-term negative effects on security in both regions and contributed to the rise of a malevolent terrorist group, the Islamic State. Exploring how electoral pressures shaped his military policy contextualizes key changes that occurred during this pivotal moment. Taken in combination, it is clear that the successful operation in 2011 had an impact akin to the first Gulf War in 1991. Both were a “catastrophic success.” The overwhelmingly positive short-term outcome taught political and military leaders the wrong lessons.