This paper considers the confluence of business internationalism, pan-Americanism, and institutional racism through an examination of the Rotary clubs’ attempts at managing their expansion into the Caribbean during and shortly after World War I. Establishing new club in the region, however, proved far more challenging than first imagined. When executives of the Haitian American Sugar Company (HASCO) joined up with other U.S. and Haitian businessmen and officials to establish a new club in Port-au-Prince in 1919, the limits of Rotary’s civic internationalism – its vision of harmony within the “parliament of businessmen” worldwide – were put to the test. Similar to debates over race, civilization, and progress at Versailles in 1919, the highest officers of Rotary debated over how to manage the organization’s international expansion in the postwar era – and, by extension, “the race question” that lay at the core of such a grand project. How did that vision play out in Port-au-Prince and how did it contrast with expansion into cities like Havana, Mexico City, Montevideo, Tokyo, and Shanghai? Finally, these questions point toward a more universal concern: What was the nature of the relationship between this kind of non-state actor, U.S. corporations, and the U.S. government during this period?