This article based on primary research including collections from the Alan Lomax Collection from the Library of Congress\u27s American Folklife Center, The Chicago Historical Society, The Pullman Company Papers from the Newberry Library, and the recently discovered Michael van Isveldt Collection from Amsterdam, Netherlands, argues that within Chicago\u27s rapidly developing Black Metropolis between World War I and II, Chicago bluesman Big Bill Broonzy treaded lightly between a world of black and white Old Settler ideas and those brought from the South by migrant New Settlers. By doing so, he helped establish a new dimension of the Great Migrations to Chicago\u27s Black Metropolis that centered on black creativity and a new kind of entrepren...