Roughly 2,000 American fugitives fled to Canada in the 1880s—mostly clerks, cashiers, and bank tellers charged with embezzlement. This article argues that these “boodlers,” as they were popularly called, were symptomatic of a late-nineteenth-century crisis of mobility. Embezzlement was a function of new kinds of mobility: migration to cities, the rise of an upwardly mobile middle class, the fungibility of greenbacks, and the growth of international transportation networks. The boodlers were some of the earliest white-collar criminals. By focusing on their unexplored story, this article contributes to the growing literature that presents the clerk as an important figure in nineteenth-century labor history. Still, the boodlers also had a more unexpected impact on the evolution of the United States' international borders, both in the popular imagination and in actual surveillance and law enforcement techniques. Through the figure of the boodler, this article examines the links between the growth of capitalism and the development of the United States–Canada border in the late nineteenth century. © 2012, Society for Historians of the Gilded Age and Progressive Era. All rights reserved.