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Why do presidents authorize risky covert operations given the potential negative impact failure could have on their administrations? I utilize a case study analysis of President Barack Obama's decision to approve Operation Neptune Spear, the raid on the compound in Abbottabad, Pakistan to capture or kill al-Qaeda leader Osama bin Laden. By developing the concept of the specter of failure, I assess the options and potential outcomes presented to the president prior to the operation. While it was ultimately a success, I argue the possibility of failure drove the president to maintain a robust decision-making process. This research provides further evidence that Obama acted as his own honest broker in the realm of national security. Additionally, evidence suggests the president and his advisors were influenced by history, especially Operation Eagle Claw, the failed attempt to rescue hostages from the U.S. embassy in Iran approved by President Jimmy Carter three decades prior. Additionally, while Vice President Joe Biden advised against the mission, his participation throughout the process improved Obama's assessment as well as informed his own choices upon entering the Oval Office as president a decade later. [ABSTRACT FROM AUTHOR]