This dissertation examines the key attempts at reaching compromise between the secessionists of the Southern States and the Republican administration of Abraham Lincoln during the Secession Crisis of 1860-61. The question of why compromise failed to prevent the Civil War is analysed first in the context of the Secession Crisis itself. Then, the nature of an American compromise and Constitutional liberty is defined with the work of philosopher George Santayana, and an overview of the three main phases of historiography, traditionalist, revisionist, and post-revisionist, is provided. After that, the two main strands of reasoning behind the long-term failure of compromise, the idea that the North and South developed irreconcilable sectional differences that could not be compromised over, and the pervasion of dualistic moral abstractions preventing reasoned discussion of political issues, are elucidated on. Ultimately, it is argued that the failure to reach an enduring compromise stemmed from fundamental ambiguity in the Constitution, particularly in regards to slavery.