Thomas Jefferson’s one-time image as a serious opponent of slavery has been heavily criticized by academics for nearly fifty years. Indeed, Jefferson’s reputation as a principal and principled progenitor of the American political tradition suffered badly in the closing decades of the Twentieth Century as historians, cultural commentators, and legal scholars focused on his racism, personal commitments to slavery, and intimate relationship with Sally Hemings, the enslaved Monticello domestic who was almost certainly the mother of one or more of his children. But while progressive thinkers soured on Jefferson at the close of the Twentieth Century, many libertarians, small government enthusiasts, neo-federalists, and champions of civic virtue remained committed to ideals and rhetoric they associated with Jefferson more than with any other founding father. When the Tea Party movement exploded onto the national political scene in the 2010 election, critics of the modern American state were quick to laud Jefferson as the favored spokesman of an allegedly simpler and purer alternative to the corrupted and degenerate federal government of the present. The original conception of America the Tea Party claimed to favor was, its members maintained, quintessentially Jeffersonian. Clearly, the Jefferson image retains power in contemporary political debates. But which image of the complex third President and drafter of the Declaration of Independence is most accurate, and which is most legitimately harnessed by citizens fighting to define the American creed in our times? Was Jefferson essentially a hypocritical racist who favored small government to protect slaveholder interests, or was he at heart a champion a universal liberty who envisioned a special role for the United States in human destiny? In this Article, I analyze the intricate relation between slavery, freedom, and the birth of the American creed by reassessing the earliest period of Jefferson’s public career when he practiced law in Virginia’s colonial capital Williamsburg, served as a member of the colonial assembly, the House of Burgesses, authored the Summary view of the Rights of British North America in 1774, and served as the principal draftsman of the Declaration of Independence in 1776. After exploring Jefferson’s legal education and the law of slavery in late colonial Virginia, the Article surveys Jefferson’s seven-year career as a property lawyer. It analyzes in detail Jefferson’s argument in Howell v. Netherland, a freedom suit appealed to the General Court of Virginia in 1770, and then considers his rhetoric respecting African slavery and alleged plans for political enslavement of British North America in his classic early constitutional state papers the Summary View and the Declaration of Independence. The natural rights arguments Jefferson employed in Howell v. Netherland, the Summary View, and the Declaration of Independence reflected a philosophy essentially inimical to human slavery. At the same time, the nuanced understanding of estates in land that Jefferson developed as a student and practitioner caused him to think in terms of conflicting and multivalent interests in property instead of Romanesque conceptions of dominium or absolute and unconditional ownership. This historically conditioned understanding of property equipped Jefferson to question the propriety and defensibility of objectification of human beings. Later in life, when he took a leading role in forming the policies of the new American nation, Jefferson de-prioritized claims for African American liberty. But in the early 1770s, Jefferson, provincial slaveholder and common lawyer that he was, embraced progressive anti-slavery tenets as yet little different from those animating the nascent anti-slavery vanguard in England and the North. Rather than the antinomian libertarian radical revered by extreme elements in the Tea Party movement or the Calhounite defender of the Slave Power reviled by some outspoken contemporary progressives, Jefferson of the Revolutionary period emerges as a sincere opponent of slavery. Tragically, as the revolutionary crisis unfolded, Jefferson learned by degrees the political utility of embracing an ever more cautious and conditional mode of discourse respecting anti-slavery goals, and an ever more gradual approach to solving the problems of political and moral legitimacy of an avowedly democratic and republican polity that remained (like Jefferson himself) heavily dependent economically and culturally on the enslavement of fellow human beings. As early as 1776, the pragmatic Jefferson was well on the way to understanding the severe limits circumscribing plausible anti-slavery for a Southern politician hoping to forge an American union committed to republican principles in what was still a decidedly monarchical and imperial world.