Chapter five discusses the first appearance of contemporary art dealers in eighteenth-century Britain. Our data show that the evolution of picture dealing from diverse proto-professional beginnings to international enterprises was based on a gradual recognition and alignment of shared economic interests between painters and professional middlemen. Of great significance here was the role of the reproductive print as catalyst.  The vast print publishing enterprises of the last quarter of the eighteenth century gave middlemen and painters the first significant opportunity to explore the benefits and pitfalls of such a union. The chapter closes with an examination of the effects of the Napoleonic Wars on this nascent and still fragile alliance. The turmoil on the Continent caused a temporary collapse of the British export trade for reproductive engravings as well as a shift of dealers’ focus away from contemporary British painting to the more profitable exploitation of arbitrage opportunities in the realm of old masters.  However, as the supply from the Continent dwindled and became riddled with fakes, middlemen’s interest moved again towards native artists.  In economic terms, this change marks the onset of the mid-Victorian art boom.