This chapter relates post-1918 Italy to the collapse of the Habsburg Empire and the ascent of the successor states, and analyses, from the Trieste’s vantage point, fascist projects, practices and networks of ‘empire’ in the Adriatic Sea, in Mitteleuropa and in the Balkans between 1918 and 1938. It focuses on three connected aspects. Firstly, the northern Adriatic was the first setting of the ascent of squadrismo, a model of violent action against ‘enemies within’ then replicated elsewhere. Secondly, Italian nationalism and imperialism aimed to reconfigure the post-Habsburg economic space and to reconnect the Adriatic with Central and Balkan Europe. Thirdly, Italian nationalist (then Fascist) élites from Trieste played a critical role, by boosting processes of empire-building and defending Austria vis-à-vis the prospects of Anschluss. In sum, the Habsburg legacies kept on shaping the dynamics of Italianization and fascistization in northern Adriatic and on feeding the search for Italy’s informal empire in Central and Southeastern Europe.