In March 1945, Pejo Peev Draganov, a former official with the Commissariat for Jewish Affairs (Komisarstvo po evrejskite vuprosi—KEV) in Bulgaria, appeared before Chamber 7 of the People’s Courts, an emergency court established in the fall of 1944 by the coalition of the predominantly Communist Patriotic Front for the purpose of bringing to justice the alleged perpetrators of anti-Jewish crimes in Bulgaria. As the head of the Skopje transit camp, where Macedonian Jews from Vardar, a Yugoslavian province occupied by Bulgaria during the war, were imprisoned before being deported to Poland, Draganov was accused of participating in Jewish persecutions. He left the courthouse a free man. Twenty-three years later, in 1968, Draganov once again appeared before a court of justice, specifically the Hesse District (RFA) Courthouse, in response to the lawsuit brought against the former minister plenipotentiary of the Reich in Sofia during the Second World War, Adolf-Heinz Beckerle, who had negotiated the deportation of Jews from the occupied territories with the Bulgarian authorities. This time, he testified as a witness for the prosecution. This arrangement was the result of a complex negotiation between the Prosecutor’s Office of Communist Bulgaria in Sofia and the West German prosecution. By taking as an entry point the career of this former defendant (in the sense of Howard Becker), the changes in his positioning on the chessboard of justice, and his movement within the space of East-West relations, the aim of this article is to question the production of post-war justice for war crimes in Europe from a transnational perspective, with a focus on its shifts over space and time. The research is based on an extensive examination of the archives of the trials held in 1944-1945 (in Bulgaria) and 1967-1968 (in the Federal Republic of Germany) regarding the judicial systems of these two states and their troubled collaboration during the Cold War.