The realization that heroism – representing either a trait or a value system – is potentially pernicious is important for both scientific and societal reasons. In this article, we adopt a psychobiographical perspective to analyze the character and life of one of Israel’s greatest heroes, Yonathan (“Yoni”) Netanyahu. Yoni was an illustrious military leader, as well as an outstanding intellectual and adored persona. He served as the commander of the special operation forces spearheading the famous Entebbe Operation during which Israeli commando forces rescued hostages taken captive in Uganda. Yoni was the only military causality in this operation, which was ultimately named after him. Subsequent to his death, his numerous personal letters were made public, allowing further glimpses into his heroic self-representations but also to the emotional distress he suffered. Applying our theory of heroic self-representations (HERS; Shahar, 2013), we analyze Yoni's letters. Our analyses confirm Yoni's tendency to construe himself as a savior and conqueror, and to identify with cultural heroes. The emotional distress Yoni suffered is characterized by depressed and anxious affect, masked by superb functioning. Qualitative analyses of the letters suggest two mechanisms of the effect of heroic self-representations on distress in Yoni's case: compulsive purposefulness and emotional seclusion.