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This contribution examines the work of Josip Smodlaka, a Croatian lawyer and diplomat who travelled to Rome at the end of the Second World War on a secret mission under the instructions of Josip Broz - Tito and Edvard Kardelj. The purpose of the mission was to assess whether there could be a direct agreement between Yugoslavia and Italy regarding the new border and, above all, the allegiance of Trieste. His mission, however, proved to be fruitless as no agreement was reached. None of the parties involved was prepared to make any compromises. While Italy refused to recognise or at least repent for the crimes they had committed during the Second World War, Yugoslavia was unwilling to accept the terms laid out by Italy, which insisted on first resolving the issue of the deportations from the Julian March. The failure of Josip Smodlaka's mission, which lasted from October 1945 to January 1946, was thus also the failure of the first attempt to reach a direct agreement between Yugoslavia and Italy. [ABSTRACT FROM AUTHOR]