In the years prior to the founding of the Pitt, the slave ridden city was originally known as Pittsburg, a pre-war city of the former United States of America prior to the Great War. After the war, the city was destroyed along with the rest of modern civilization and left in ruins. Two centuries later, groups of survivors colonized the downtown areas of the former city and set up shop, but they were not alone as raiders, rape gangs, and other criminals tormented them and made it a target for the Brotherhood of Steel. The Brotherhood sent in a task force and conducted the "Scourge" where they intended to liberate the oppressed people of the ruined city, but they killed most of its inhabitants during the operation and took the survivors away to their bases. Ishmael Ashur was the supposed only casualty of the operation and was left behind after he was thought to be dead from an explosion. He later came across raiders and took control of the gang and later established himself as their leader and enslaved many people, brought them to Pittsburg, and founded The Pitt where he was its sole autocratic ruler.
Years later in 2277, a former slaver by the name of Wernher came across the mysterious but legendary Lone Wanderer who asked for his help. Wernher had friends stuck in The Pitt and he wanted to free them and so, he asked the Lone Wanderer for his help to which he said yes and helped him in his plot. The Lone Wanderer eventually met up with Media, the co-leader in the conspiracy and the matriarch of the Pitt slaves, and she helped him tell where the "cure" was and had the wanderer disguised as a slave and participated in various matches in The Hole, a battle arena for slavers to watch slaves fight in. After finding steel ingots and meeting with Ashur, the slaves rioted and began their rebellion.
While the Lone Wanderer was talking with Ashur who was seeking to convince him into joining his ranks and offered a place for him in The Pitt, slaves outside began to riot and turned on their masters. Slavers were overrun and killed and many raiders along with them. Their gear was stolen and was used by the slaves to instigate their rebellion and helped overrun large portions of the city. Ashur ordered the Lone Wanderer to supress the rebellion, but he didn't follow through and he ended up shutting down Uptown's lights and overran it with Trogs who devoured and killed the raiders, further weakening their grip on the city. Ashur was eventually confronted andkilled by the Lone Wanderer along with his second-in-command, Krenshaw.
Following the death of Ashur, the remainder of his forces surrendered as they were too thinly spread and outnumbered at the hands of their former slaves who had them arrested and imprisoned. The Wicker Man statue was eventually destroyed and brought down and its ruins were used by Wernher during his speech where he proclaimed the foundation of the Free State of Pittsburg, a new demcratic state born from the ashes of slavery and the old world two days later. Slavery was officially abolished as well and the citizens went to work rebuilding Pittsburg and trying to establish a free and democratic state.