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Following the NCRCF Uprising, the town's mayor Joseph B. Steyn set his sights on the newly formed Powder Gangers. Hoping to make an extra profit, he extended an invitation to the town to the Powder Gangers, offering them the town's main attractions, such as chems and hookers. A Caesar's Legion member named Vulpes Inculta met with Steyn under the guise of "Mr. Fox". He convinced Steyn to grant the Legion entry to the town to capture the NCR soldiers and Powder Gangers that passed through the town in exchange for a large sum of money. Steyn was oblivious to the fact that Inculta was in fact tricking him into the destruction of Nipton.
The Legion later swarmed the town and restrained all citizens, and murdered any citizens that defended themselves from the attack, resulting in the Nipton Hall being littered with their corpses. After resolving the situation and locating all citizens to the center of the town, a lottery was announced, and tickets were handed out to all citizens. When the lottery was announced, the first round of the draw was for the "lucky losers", who were decapitated. Second came the crucifixions, which contained the majority of the citizens, and took a long amount of time to undertake.
Joseph Steyn's ticket saw him burned to death in a tire fire. For third place, the ticket holders were enslaved and sent to the Legion raid camp. For second place, Boxcars' legs were beaten with hammers, leaving him crippled and sat on a chair in the Nipton General Store. The first place winner, Oliver Swanick, was allowed to walk free.
The aftermath of the Nipton massacre appears in Fallout: New Vegas.