In this dissertation, I argue for the need to examine the emergence of licensing and branding practices prior to media conglomeration. Through an in depth exploration of George Trendle’s licensing arrangements for the Lone Ranger and Green Hornet brands’, I trace how contemporary licensing practices took root while also arguing for the need to analyze licensors as cultural intermediaries with particular occupational identities, attitudes and values that shape their daily business practices. This project uses historical records archived at the Detroit Public Library and the American Heritage Center in Laramie Wyoming to re-write the history of trans-media relations between the years 1933-1966 through the lens of one of the most successful independent licensors of his era. Trendle not only shaped future licensing practices, but the degree of independent managerial authority he exercised over his brands also exceeded the norms of most intermediaries, leading to his eventual marginalization within the emerging media conglomerates of the late 1960s.