This study analyzes the medical records found in the Annals of the Joseon Dynasty (朝鮮王朝實錄) and the Diary of the Royal Secretariat (承政院日記) to examine the chronic illnesses of King Jeongjo (正祖, 1752-1800), the 22nd monarch of the Joseon Dynasty. The analysis focuses on how his recurring diseases were shaped by a complex interplay of constitutional factors, psychological stress, and political circumstances. The most frequently documented conditions were gyeokgi (膈氣, chest qi stagnation) and fever syndromes (熱症), which are attributed to digestive weakness and emotional strain. Gyeokgi (膈氣) manifested through symptoms such as indigestion, abdominal pain, and chest tightness, while fever syndromes(熱症) included sensations of internal heat, insomnia, and emotional agitation. These were closely tied to Jeongjo's sensitive and impatient temperament, the trauma of his father Crown Prince Sado's unjust death, and the burdens of political leadership. Additionally, Jeongjo regularly suffered from seasonal disorders such as seojeung (暑症, heat illness), gastrointestinal distress (霍亂), and colds-symptoms likely linked to his chronic digestive frailty and lowered immunity. In his final years, the development and aggravation of boils ultimately led to sepsis, presumed to be the direct cause of death. This study illustrates how Jeongjo's health was influenced by a convergence of hereditary constitution, mental and emotional strain, and the weight of kingship, offering a deeper understanding of disease and medicine in the late Joseon royal court.