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The attacks of September 11, 2001 constituted one of the most significant moments in recent memory. Perpetrated by the terrorist organization Al-Qaeda, nearly 3,000 people died in the attacks and 25,000 others were injured. The material damages were staggering. Settling the insurance claims around the destruction of the World Trade Center proved to be a puzzle in what came to be a major inflection point for the insurance industry. SwissRe was the lead insurer of the buildings in a multi-party insurance policy that totaled USD3.55 billion. Silverstein Properties held the lease of the buildings for 99 years and contested the insurance policy payout limit. The Port Authority of New York & New Jersey owned the buildings and with the government planned a USD9 billion rebuild at Ground Zero. The case offers an insider’s look at how various stakeholders from around the world approached the negotiations and sought to reach an outcome to settle the dispute. Further, it sheds light on the backgrounds, thoughts, and motivations of the major players, all against the background of what was one of the greatest tragedies of modern history.