Despite supposed Choctaw authority after 1830 over bituminous coal deposits of southeast Indian Territory, in the last decades of the 1800s, non-indigenous “robber barons” such as Jay Gould formed corporations to mine and transport Choctaw coal. Thousands of non-indigenous settlers, mostly miners from Europe and Mexico, streamed into this area that in 1907 would become Oklahoma, United States. They settled in a string of “company” camps and towns run by the mining corporations along the coal seams. Syrian merchants followed and settled among them to sell them goods. Drawing on family records and photographs, unpublished histories, naturalization documents, newspaper articles, city directories, and secondary sources such as town histories, this paper describes various settler roles played by Syrian immigrants in the mining towns of the Choctaw Nation, and, later, Oklahoma. It focuses on Syrian positions and practices related to capitalism. Federally unregulated and operated by radically laissez-faire capitalists, the Choctaw mines constituted “the most dangerous mines in America.” Initially, company camps and towns lacked amenities and services except for exploitative company stores. Partly due to these Gilded Age conditions, by the second decade of the 1900s, eastern Oklahoma mining towns were known for their organized socialist politics. Situated within these tensions, Syrian merchants articulated and demonstrated a range of political economic values and ideas. After their arrival “broke” the hold of the company stores, Syrians built interethnic alliances to help form some of Oklahoma’s earliest commercial clubs and chambers of commerce; public services, such as fire departments; cooperative utilities, including cotton gins; and unions of merchants. With other townspeople, recent immigrants as well as established Anglo-Americans, Syrians helped develop the “company towns” in Choctaw Nation into places that served grassroots entrepreneurial and human interests.