Arguably our most obscure president, and generally judged mediocre at best, Millard Fillmore came to the presidency in July 1850 when his predecessor, Zachary Taylor, unexpectedly died. Despite his relative anonymity, Fillmore was thrust into the nation’s greatest historical argument the great debate concerning the future of slavery in the republic. With considerable political aplomb, he helped guide the passage of the measures collectively known as the Compromise of 1850, including the sensitive and controversial Fugitive Slave Act. Rather than resolve the agitation, these measures gave way to a decade of rancorous conflict which brought about the Civil War. This interpretative study seeks to understand why this president remained anchored to a past that was no longer effective in his own time.