Thomas Jefferson was substantially influenced by Classical Greece and Rome, the lessons from which he shared with John Adams in their retirement correspondence. His friendship with Adams, formed as they worked side-by-side to found a nation, endured the pressures of the party factionalism of the 1790s only to collapse during the contentious election of 1800. For over a decade they were not on speaking terms. However, both men corresponded with fellow founder Benjamin Rush who mediated their dispute using the classics as an olive branch. The story of how the classics helped bring them back together is deeply moving, yet it has only been touched upon briefly in the secondary literature. Once resumed, their correspondence was permeated with classical allusions. From then until their deaths on the same day, Jefferson and Adams carried out a colorful, classical correspondence. Jefferson’s retirement correspondence with Adams illustrates the profound and far-reaching influence of the classics over him.