Croatia’s official government policy towards enlargement into the Western Balkans is shaped by a number of different, sometimes complimentary, sometimes conflicting factors. When it joined the EU as the Union’s 28th member in July 1, 2013, this country of 4.3 million inhabitants ranked 21st in terms of both population size and GDP making it one of the smallest countries in the organization. In foreign policy terms, such small states face the task of either quietly tending to their affairs, oftentimes under the wing of some larger power, or of attempting to capitalize on certain key issues of specific characteristics which would allow them to occupy a niche in the international system. The current Croatian government has opted for the latter strategy, attempting to capitalize on the country’s shared historical, political and cultural legacies with other non-member states in the region to position Croatia as a champion for enlargement. At the same time, Croatia’s legacies with neighboring states and its historical drive to leave the Balkans complicates its role as an advocate for EU expansion into the region. These competing legacies interact with domestic political cleavages in ways that create different pressures on political actors representing various political options. While this project focuses primarily on Croatian foreign policy, it contains many important lessons for other small current and future EU member states.