Purpose: This study aims to examine the diplomatic personality of Caliph 'Umar (d. 23/644) within the framework of the psychohistorical approach, revealing the nature and extent of the relationship between historical actors and the personality traits underlying their actions. Psychohistory, which integrates history and psychology, seeks to understand individuals' inner worlds, character structures, and motivations throughout historical processes. Accordingly, the study analyzes 'Umar's personal development, leadership style, and diplomatic competence from a psychological perspective. It is significant in that it evaluates one of the formative figures of Islamic history not only through historical facts but also through psychodynamic insights into his leadership and decision-making processes. Method: The research employs a qualitative document analysis method. Data on 'Umar's life, decisions, and diplomatic relations were collected from both classical and modern sources and interpreted through relevant psychological theories, particularly psychoanalytic perspectives. The data were analyzed using descriptive and conceptual analysis, and the findings were thematically categorized and compared with existing literature. Findings: The analysis reveals that 'Umar exhibited both charismatic and partially paternalistic leadership qualities. His empathy, sense of justice, communication skills, and strategic thinking were key determinants of his diplomatic success. His experiences in transitioning from tribal life to state governance fostered a pragmatic and stable administrative model, characterized by composure and decisiveness during crises. From a psychoanalytic standpoint, traits such as a strong superego structure, secure attachment patterns, and mature defense mechanisms-particularly sublimation-were reflected in his leadership behavior. Conclusion: The psychohistorical analysis demonstrates that 'Umar's diplomatic competence was shaped by both conscious strategies and unconscious psychological dynamics. The study highlights the applicability of psychohistorical methods in Islamic historiography and contributes to interdisciplinary research combining psychology and history. Furthermore, 'Umar's leadership model offers valuable insights for contemporary political and diplomatic practices emphasizing empathy, justice, and participatory governance. Future studies are encouraged to apply psychohistorical approaches to other historical figures for comparative analyses of leadership typologies.