Chapter 6 describes Headen’s successful application of Wood’s “coalition economics” to the automotive industry. Focusing on the Headen Motor Company, which Headen founded in Chicago in 1921, the chapter describes his amassing of a diverse coalition to finance the effort. Attracting investors, black and white, male and female, Northern and Southern, his coalition included business owners, ministers, political figures, journalists, fraternal and civic leaders, club women, and auto racing enthusiasts. Prominent members included national figures Robert S. Abbott, publisher of the Chicago Defender, former Carolina Congressman George Washington Murray, and Florida educator Blanche Armwood Beatty. The chapter also addresses Headen’s emergence as a leading proponent of transportation technologies in the black press; his technological vision; his growing interest in dirt-track racing; and his establishment in 1924 of the Afro-American Automobile Association, a motorist’s support organization.