The secrecy enveloping the past of public figures — journalists, politicians, and business moguls — has been plaguing democratic transition all across the Central and Eastern European region. In Bulgaria, the public has faced at different stages of the transition the uncomfortable moral crisis of reconciling the communist past with the political and cultural presence. In this process, journalists and media professionals play a vital role as critical agencies of discovering and disseminating the facts concerning the secret communist past of public figures. The situation is further complicated when journalists themselves are implicated in collaborating with the communist secret service, while at the same time, serving as prominent voices of dissent and political change. This paper examines the ramifications of these problems for press freedom and self-censorship, when not only journalists but media owners themselves, find their names on the “blacklist” of former secret agents and spies.