In 1977, Roberto Bolaño moved from Mexico City to Paris and eventually to Spain. His works from the beginning of the 80s such as Consejos de un discípulo de Morrison a un fanático de Joyce (with A.G, Porta) and Antwerp, set in Catalonia, and A Little Lumpen Novelita - a story set in Rome -, portray the social crisis at the end of the Spanish Democratic Transition and the so-called Lead Years in Italy. The Costa Brava landscape and the town of Blanes, where he resided from 1985 onwards, would become the settings of The Skating Rink and The Third Reich. The 1992 Barcelona of Distant Star, the 1939 Paris of Monsieur Pain, and other European settings of Woes of the True Policeman and 2666 recreate the dislocations of different lives in exile and the conflicts of those who cross the West’s established borders and logic, transgressing national identitary configuration itself. This chapter will map the complex reflections of Bolaño, an icon of the global writer, on the Spanish and European reality of the end of the 20th and beginnings of the 21st Centuries, as well as on the potential, limitations, and cracks within these trans-Atlantic connections.