In this chapter we examine foreign direct investment (FDI) flows between Europe and Latin America, paying particular attention to the European expansion in the region—its drivers and main players. While the United States had traditionally been the most important investor in Latin America, the wave of privatization of the 1990s represented an opportunity for newcomers from Europe (mainly from Spain) to expand in the region. In that decade, Spanish companies seized the opportunity and became major players in key sectors such as utilities, banking, telecommunications, and infrastructure and beyond. For Latin American investors, on the other hand, the United States continues to be the most important destination (primarily due to investments by Mexican firms), followed by Spain. The latter provides a platform for subsequent investments in Europe for many Latin American firms. Portugal plays a similar role for Brazilian companies seeking to invest in Europe. These two-way investment relations reinforce economic, but also cultural and historical ties. The future of these relations will either bring these two regions closer together or drive them apart.