Riga and Odesa (Odessa) rank among the Russian empire's foremost nineteenth-century ports. These port cities, respectively located on the Baltic and Black Seas, enabled imperial Russia to trade huge amounts of goods, boosting its burgeoning economy in the second half of the nineteenth century. We argue that, despite the distance separating the two cities, it is only in relation to each other that their full significance emerges. This article explores the histories of Riga and Odesa, examining their situations within the Russian empire's economic geography and taking a closer look at the interrelationships between the two ports. In our view, this history is more than a narrative of competition for the premier position among the ports of the Russian empire; it is also a tale of local initiatives, engagement with the imperial center, lobbying for imperial financial support, relationships of economic interdependence, and an example of the crucial role that ports at the supposed periphery of an empire played in a globalized economy.