Repression increases dictators and authoritarian regimes' prospects of survival. The existing literature, however, limited by available data, rarely explains the role a dictator plays in the repression to ensure his interests. This article employs the Taiwan Transitional Justice Database to address this question. The military courts, on which the Kuomintang government highly relied during the authoritarian rule, had two functions in repressing the dissidents: 1. to sentence the accused on the basis of the severity of the threat against the regime; 2. to submit the more threatening cases upwards for the president's review before closing the trial. In the latter scenario, it has been suggested that the low-ranking judges would tweak their judgments by ＂second guessing＂ their superiors' preference. This article tests the ＂second-guessing＂ hypothesis, examining how the intervention of Chiang Kai-shek, the dictator and the president of the Republic of China on Taiwan, influenced the judges' behaviors and the trial process. We find that the military court was evidently pandering to the Generalissimo, as our findings show that the Chief of the General Staff was more likely to reject the lower court judges' judgments and review the cases multiple times, and the lower court judges more likely to be more cautious in handing out sentences to accommodate the top ruler's preference, if Chiang Kai-shek vetoed the judgments of the lower court or required their retrials more often in the previous year.