Whereas the micro- and macro-oriented leadership literatures have often studied leader competencies necessary for effective performance, the role of leader character in relation to competencies and performance has been to a large extent neglected. Our work seeks to shift the scholarly dialogue by introducing the concept of character-competence entanglement, which reflects the binding between character and competence over time. The highest degree of entanglement represents the deep and more persistent interconnection and mutually-reinforcing effect between highly-developed leader character and highly-developed leader competence, whereas in cases of low entanglement, character can be activated temporarily in a particular context to help strengthen the relationship between competence and performance. Our core proposition is that high character-competence entanglement will lead to extraordinary performance over time. In addition, we emphasize that relying on naturally-occurring learning opportunities and the processes of “learning-by-living” both outside and inside the organization will positively impact the development of character-competence entanglement