In the summer of 1800, as white Virginians organized to elevate Thomas Jefferson into the Executive Mansion, slaves in half a dozen counties prepared to rise for their freedom. In early August, following the funeral of a black child, the slave known only as Gabriel, a Richmond-area blacksmith and the plot’s mastermind, announced to the mourners that he had a plan to fight “for his Country.” At that moment, another slave named Jack Ditcher challenged Gabriel’s leadership by asking the men at the meeting “to give him the voice for General.” The black Virginians decided to resolve the question as did white Americans that fall. They held an election, and “upon the votes being taken, Gabriel had by far the greater number.”

The plot failed, washed away by heavy rains and crushed by Governor James Monroe’s militia. Among those tried was an unnamed slave who compared himself to George Washington, saying that he had “adventured [his] life in endeavouring to obtain the liberty of my countrymen, and [was] a willing sacrifice in their cause.” He and twenty-six other enslaved Virginians, including Gabriel, who was then twenty-four-years-old, paid for their desire to be free with their lives.

Two centuries and far too many elections later, white and black Virginians flocked to the polls to elect Barack Obama the nation’s first African American president. It did not have to take this long. Four years before Gabriel swung from the Richmond gibbet near Fifteenth and Broad Streets, a professor of law at the College of William and Mary devised a plan to gradually eliminate slavery from Virginia, the state with the largest black population in the young republic. St. George Tucker taught law when not serving as judge on the state’s general court, a sinecure that allowed him to speak his mind more freely than those who had to run for public office. Well aware that slavery was collapsing across the North, Tucker corresponded with white politicians, reformers, and ministers in Pennsylvania and Massachusetts, seeking information on how those states had slowly eradicated slavery. Armed with their responses, Tucker drafted A Dissertation on Slavery: With a Proposal for the Gradual Abolition of It, in the State of Virginia.

The pamphlet, published in Philadelphia in 1796, ran to more than one hundred pages. Although it was hardly the sort of proposal that would find much support in the state’s small free black community, it at least established a basis for discussion. Tucker suggested that every black woman born after “the adoption of the plan [should become] free” at the age of twenty-one. Any of her children, regardless of gender, born after that birthday, would be born free. All freed blacks were to “voluntarily [bind] themselves to service for a year before the first day of February annually,” or it would be done for them by the “overseers of the poor.” No freed slaves could vote, hold office, or acquire “any estate in lands or tenements, other than a lease not exceeding twenty-one years.” Neither could they bear arms, marry whites, serve as an attorney, or prepare a will.

What made Tucker’s plan different from previous Virginia proposals for gradual emancipation was its specificity—down to what sort of blanket black women were to be granted at age twenty-one—and the fact that it did not require freedpersons to be colonized outside the nation’s borders. Although Tucker hinted that some former slaves might be inclined to migrate into the Spanish colonies of Florida or Louisiana, forced emigration, Tucker insisted, was both cruel and financially impossible. His assumption was that most blacks would remain in Virginia as a landless and politically powerless agricultural working class. Financial concerns aside, this was a frank recognition that most planters would never permit an end of slavery unless they could retain their black labor force. In his proposal, Tucker emphasized, the “earth cannot want [black] cultivators.” In short, his plan allowed the gentry to abolish slavery while retaining their class prerogatives.

Tucker respectfully presented his plan to the General Assembly, where with little fanfare and even less discussion, A Dissertation was “ordered to lie on the table.” A dejected Tucker forwarded copies to his friend Jefferson, telling him that he hoped the hostile “reception that it met with from some individuals” in the assembly was not indicative of “its merit.” But the legislature’s refusal to implement—or even seriously consider—Tucker’s gradualist scheme was tantamount to a collective, if possibly unconscious, decision to retain slavery. Jefferson’s noncommittal response was characteristic of both the man and his class. He hoped that Tucker knew of his “subscription to [the pamphlet’s] doctrines” but added that any “mode of emancipation” must be a “compromise between the passions, the prejudices, & the real difficulties which will each have their weight in that operation,” as if Tucker’s conservative plan was not all of those things.

History is a series of roads, all leading to the present. Some of them, sadly, were roads not taken. By failing to implement Tucker’s plan, Virginia’s state assembly not merely made Gabriel’s plot inevitable, they effectively voted to perpetuate a system that eventually led to the death of 600,000 young men in the years between 1861 and 1865.

Last month in his inaugural address, President Obama spoke of the “long rugged path towards prosperity and freedom” waged by so many Americans, including young men like Gabriel and Jack Ditcher, who “endured the lash of the whip.” The president also spoke of “the challenges we face,” and he warned that the time has passed for “putting off unpleasant decisions.” Too many Virginians chose the easy road in 1796; as Patrick Henry admitted, slavery was “repugnant to humanity,” but he chose not to free his slaves due to the “general inconveniency of living without them.” More than two centuries should not have passed between execution of Gabriel and the election of the nation’s first black president, but Gabriel’s fate serves as a grim reminder of the high cost of inaction. Our republic faces hard decisions, and this time politicians and voters alike must face up to them. The time has come, as President Obama eloquently put it, to “pick ourselves up, dust ourselves off, and begin again the work of remaking America.”