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This article discusses a rare successful prosecution of a head of state by a modern international criminal court. The case involved former Liberian president Charles Taylor. Taylor, who was charged and tried by the United Nations-backed Special Court for Sierra Leone (“SCSL”), was convicted in April 2013 for planning and aiding and abetting war crimes, crimes against humanity, and other serious international humanitarian law violations. He was sentenced to 50 years imprisonment. The SCSL Appeals Chamber upheld the historic conviction and sentence in September 2013. Taylor is currently serving his sentence in Great Britain. This article, from an insider who worked as an interim court-appointed defense attorney during the opening of the trial in The Hague in June 2007, is the first to comprehensively evaluate this significant international case since it concluded. I expose the numerous controversies that dogged the trial of Liberia’s former president — from the questions that arose about how best to sequence peace for Liberia and justice for Sierra Leone following the prosecution’s initial unveiling of his judicially sealed indictment through to concerns about whether he should be tried in the heart of Europe, as opposed to Africa, to the completion of appeals. I conclude that the trial of former President Taylor is significant for the SCSL because he was the most powerful suspect to be indicted by the court. Although it may be too early to draw definitive conclusions, a key lesson that we can derive for international criminal justice is that the indictment of a sitting president for international crimes may sometimes help loosen his grip on power, thereby enabling his subsequent prosecution.