The history of the Jews in Bulgaria is fraught with conflict and betrayal particularly during World War II when the Bulgarian government allowed the Nazis to deport most of the Jews to Treblinka as reported by the New York Times on March 2, 1941. This paper studies how the some Sephardic Jews were able to use their connection with Spain as a legal loophole to escape deportation. I examine newspaper articles, trial testimonies, legal documents, and a rare unpublished manuscript that deals with the testimony of two Jews who managed to escape deportation to Treblinka all in order to elucidate the nature of the complicity of the Bulgarian government with the Nazis. I seek to understand how the surviving Bulgarian Jews who remain in Sofia negotiate nationalist loyalty in light of this betrayal.