This research investigates the general causes of mistranslation of Syrian political discourse and in particular the causes that lead to pragmatic failure in translation. It starts by highlighting the key concepts in major theories of translation, including the review of the importance of pragmatics for translation. Next, it moves to highlight the necessity of exploring the importance of pragmatic translation equivalence in bridging the gap between the source text (ST) and the target text (TT). It also clarifies pragmatic failure in translation, which could be classified as pragma-linguistic failure, or socio-pragmatic failure or both, and then reviews the translation differences between Arabic ST and TT(s). The source of the research data was four interviews by the Syrian President Bashar al-Assad. The four interviews together with their official and unofficial translations were presented in a questionnaire format to the research participants in a comparable manner, so that the contrastive research could be conducted. Each three sentences, the Arabic ST and the TTs, were put in a table designed to perform the contrastive analysis and collect the data necessary for answering the research questions. The questionnaire data was collected and analysed and the results of analysis reveal that the observed mistranslations in the unofficial TT (70.14%) were more than those observed in the official TT (29.85%). Out of these percentages 79.84% of the unofficial mistranslations caused pragmatic failure. The causes for these mistranslations were grammatical (7.75%), semantic (20.93%), culture-related (22.48%) and the other deviations under the previous three types together (28.68%). 20.15% of the official mistranslations caused pragmatic failure. The causes for these mistranslations were grammatical (0%), semantic (11.24%), culture-related (0%) and the other deviations under the previous three types together (8.91%). Further research in the light of findings in this research has been suggested.