A critical component of military success is the relationship between civilian and military leaders. Most essential is the degree of rapport between the President and senior military officers during times of conflict. Effective working relations between the constitutional Commander-in-Chief and uniformed military leaders have proved an enduring challenge throughout United States history. This paper looks at the bonds between presidents and generals during the American Civil War of 1861-1865. Specifically, the study explores the professional and personal relationship between President Abraham Lincoln and two of his leading army commanders, Major Generals George B. McClellan and John Pope. The paper examines a fundamental question of strategic leader relationships: what leads a President to place trust in a senior military leader in wartime and what factors contribute to the President retaining or losing that confidence in the military commander. The paper also draws insight and conclusions from these Civil War strategic leader relationships that serve as relevant considerations for today's governmental and military strategic leaders.