Thomas "Billy" Caldwell (1782-1841) was born in a Mohawk refugee camp during the American Revolutionary War. His mother was a Potawatomi woman. His father was a Scottish immigrant trader who had dealings with many Native tribes. Billy grew up hearing English, French, Potawatomi and Mohawk and became adept at picking up new languages. His father abandoned Billy and his mother to move to Detroit, but later took custody of Billy, providing him with a White education and raising him in the Catholic faith. At the age of 15, Billy began learning the fur trading business, becoming useful to his employers because of his facility with the Potawatomi language. He also became friendly with Tecumseh. When the War of 1812 broke out, Billy went to Canada, hoping to use his father's influence to gain a commission in the British Army. He was commissioned a captain in the British Indian Department, working as an interpreter.
Billy got his first taste of how the British treated their Indian auxiliaries, abandoning them after Tecumseh's death in the Battle of the Thames. Caldwell was one of the last men to see Tecumseh alive, reporting that the Shawnee leader had been shot in the chest, but was still under his own power. Billy's father was appointed Superintendent of Indians for the Western District, but removed for inadequate distribution of rations. Billy was appointed in his father's place, but soon forced out of the position. His father had died and he inherited land in Canada, but decided to return to the United States and settled in Chicago. He went to work for a local fur trading company and became active with the tribes in the area, particularly his mother's Potawatomi, the Ojibwe, Ottawa, and others. He gained the trust of both White authorities, being made a Justice of the Peace for Peoria County, Illinois. Later, when a vacancy for a chief's position appeared among the Potawatomi, U.S. authorities plugged him into the job, bypassing traditional Native norms. Through his own efforts, Billy was eventually accepted by the Natives as a chief. By 1830, Indian Removal had come for the remaining Nations of the Old Northwest, among them the Ottawa, Potawatomi and Ojibwe, who appointed Billy as their spokesman. He helped negotiate the Treaty of Prairie du Chien. Caldwell was given 1600 acres on the Chicago River for his cooperation in the treaty process. He helped found the first Catholic church in Chicago on a portion of the land. In 1833, he was among several Native leaders who negotiated the Treaty of Chicago. By this treaty, the Potawatomi ceded the last of their lands in Illinois, Wisconsin and Michigan. Caldwell was among those leaders who received a lump sum payment and lifetime annuity in exchange for his signature. He began selling off portions of his Chicago land, but did not see any profit from it because the land sales were later nullified. The remaining land is now the Cook County Forest Reserve.
In 1835 Caldwell led his band of Potawatomi away from Illinois and resettled in Platte County, Missouri. In 1836, they were removed again, to Trader's Point on the eastern bank of the Missouri River in what is now Iowa, in present-day Council Bluffs, Iowa. A devout Catholic himself, Caldwell welcomed Jesuit mission Jean de Smet to work among his people. Alcohol traders were active, too, despite the efforts of Caldwell and de Smet to stop them. Billy Caldwell died in 1841, possibly of cholera. Later, his son would attempt to reclaim portions of his father's Chicago land holdings but without success.
Developers in Chicago had decided that the mixed race Potawatomi leader Billy Caldwell was a good branding name for a number of products, including cigarettes. They developed a Billy Caldwell golf course, which still exists today. His native name, Sauganash, which simply means "one who speaks English", made an even better brand, one with more flair. The Sauganash Hotel, which also stands, and a residential area in Chicago are called by that name. Neither Billy nor his heirs realized money from any of it.
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