As one of the treaty signers in 1829 and 1833, Billy Caldwell and others negotiated the sale of 5,000,000 acres of land in northwest Illinois, resulting in the removal of all Native American tribes in the state of Illinois. Billy Caldwell, also known by his Indian name, Sauganash, was an influential figure in both Native American and early American history. Born in 1780 after the Revolutionary War to a British Army officer and a Mohawk mother, he grew up amidst a confluence of cultures: British, Irish, and Indigenous. He later became a prominent chief of the Potawatomi people, known for his diplomatic skills and efforts to negotiate land treaties with the U.S. government during a time of great upheaval for Native American tribes in the Midwest. Caldwell's legacy includes his work on two important treaties here in Chicago, the 1829 Treaty of Prairie du Chien and the 1833 Treaty of Chicago, which not only resulted in the cession of vast tracts of land but also helped secure land for his people, ensuring their future during a time of forced relocations and growing tensions between Native tribes and the U.S. government. Beyond his political and diplomatic work, Billy Caldwell is remembered for the complexity of his life. He straddled two worlds; advocating for his Native community while also navigating the growing American political landscape. His efforts to preserve peace during turbulent times, and his ultimate displacement with his people, reflect the broader story of Native American resilience and adaptation in the face of colonial expansion.