On his gravestone, Jefferson included the Declaration of Independence, the Statute of Virginia for Religious Freedom, and the founding of the University of Virginia as the three achievements he wished to be remembered by. For its rhetorical flair and its symbolic value, the Declaration of Independence is the one thing that Jefferson is above all remembered for. Despite the time-honored value of this document, the revolution was already in motion when Jefferson wrote it, and events would have proceeded in kind whether with it or with a similar document of its kind. Ultimately, Jefferson made other contributions that were more significant to the lifeblood of the United States. The Statute of Virginia for Religious Freedom did a tremendous amount to pave the way for a firm separation of church and state. The Louisiana Purchase extended the power of the executive tremendously, and forever transformed the nature of the emerging nation, placing it squarely on a trajectory of expansion and empire. Beyond the things which he chose to do, Jefferson left a legacy in the things he chose not to do. By holding out from a European alliance or a declaration of war, Jefferson set his country on an economic downturn that, in spite of itself, eventually strengthened the domestic fabric of agriculture and industry. And by continuing to countenance the institution of chattel slavery, Jefferson passed the burden of regional conflict on to the next generation, where it would eventually smolder and burn in a Civil War that would mold the shape of the nation forever after.

Two examples spring immediately to mind: economy and slavery. As President, Jefferson aspired to eliminate the national debt entirely by tightening purse strings across the board, cutting the scope of the federal government and the size of the military. However, in playing host to society at Monticello and at the President's House, Jefferson spent extravagantly, leaving no stone unturned and no nickel unspent. Such ostentatious living propelled Jefferson into a severe spiral of debt that he never recovered from. As a result, while his country benefited from his conservative fiscal policies, his heirs were the poorer for his liberal spending habits, finding themselves stripped of the estate that by rights was meant to be theirs. With regard to slavery, Jefferson maintained a moral opposition to the peculiar institution throughout his life. He authored and supported various gradual emancipation plans, and proposed unsuccessfully to limit the spread of slavery into new territories within the United States. However, Jefferson maintained a significant population of slaves on his estates throughout his adulthood, and passed down a group of slaves to his eldest daughter upon her marriage. And although Jefferson did emancipate certain slaves in his old age, he also rented and sold many others to cover his constant debts.

Jefferson aspired to introduce a measure of equality into Virginia by reforming three major planks of the society: education, politics, and religion. His support of free public schooling was unprecedented. Even though Jefferson believed the importance of merit, he believed in equal educational access to all students regardless of background. With regard to politics, Jefferson broadened the representation of white male suffrage by abolishing primogeniture and entail and by easing naturalization requirements, thus increasing the number of land-owning citizens. As to religion, by accomplishing the disestablishment of the Anglican Church, Jefferson precipitated a measure of religious freedom previously unknown, thus allowing each to worship in his own way. For the above reasons, Jefferson significantly leveled the playing field for white males, although equal opportunities for blacks, natives, and women would be deferred for centuries, even down to this very day.