This chapter examines how Anthony Overton dramatically diversified his financial interests during the 1920s. In 1922, Anthony Overton assumed the presidency of Chicago’s Douglass National Bank (the second black-owned bank to receive a national charter). Two years later, Overton started the Chicago-based Victory Life Insurance Company. In 1927, Victory Life became the only black-owned insurance company granted the right to conduct business in New York State. Following this business coup, Overton, in some circles, became regarded as “the merchant prince of his race.” To further enhance his growing status as a business magnate during the 1920s, Overton built two major commercial structures in the heart of black Chicago’s commercial district (the Overton Building and the Chicago Bee Building).