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The fellow Founding Fathers James Madison and Patrick Henry did not get along. The two Virginians had very different philosophies on the proper role of government and its relationship with liberty, divisions that came to a head during their famous debate in June 1788 over the ratification of the U.S. Constitution. But perhaps more significantly, the two men were also from different generations and very different family backgrounds. Henry, the son of a Scottish immigrant, came of political age during the colonial era. He made a name for himself in Virginia politics with a fiery speech to the House of Burgesses in 1765, where he sharply denounced the Stamp Act and the British monarchy. Taking the floor to address men many decades his senior, the twenty-nine-year-old Henry, “in a voice of thunder, and with the look of a god,” declared that “Caesar had his Brutus—Charles the First, his Cromwell—and George the Third…may profit by their example.” As cries of “treason!” erupted from the assembled burgesses, Henry, displaying the penchant for pithy declarations that later produced his signature one-liner, “give me liberty, or give me death!” calmly responded, “If this be treason, make the most of it.”
In the audience that day was a twenty-two-year-old law student named Thomas Jefferson, and it would not be the last time that the two men’s paths would cross. The feud that developed between these titans of the founding era, Jefferson and Madison on one side, Patrick Henry on the other, culminated in a gerrymander that would threaten not only the careers and political reputations of those involved but the very existence of the United States itself. In 1788, with the ink on the Constitution not yet dry, Henry used his political clout in the Virginia general assembly to gerrymander Madison’s home district. His goal was to deny his nemesis a seat in the First Congress, the very legislative body that gave us the Bill of Rights. If he had succeeded, the fragile compromise that shepherded the fledgling union through its turbulent early years might have been shattered. This chapter is the story of how gerrymandering almost blew up the American system of government on the launchpad.
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Madison’s upbringing could not have been more different from that of the man who later became his bitter enemy. While Henry’s father was a first-generation immigrant and minor planter, Madison’s family had settled in Virginia in the early seventeenth century and owned one of the largest tobacco plantations in the colony. Fifteen years Henry’s junior, Madison cut his political teeth during the revolutionary era as a member of the Virginia House of Delegates, and later as a representative in the Second Continental Congress. Henry had also been a member of that body, although their tenures did not overlap. Henry served alongside Jefferson in 1775, leaving less than a year before the Congress adopted his Declaration of Independence, while Madison served later, observing firsthand the dysfunction of the newly established American republic under the Articles of Confederation.
Though Jefferson had been impressed, as everyone would come to be, with Henry’s powerful oratory, he nevertheless viewed him as all style and no substance. “His imagination was copious, poetical, sublime,” he later wrote in his memoirs, “but vague also. He said the strongest things in the finest language, but without logic, without arrangement, desultorily.” In a letter to George Rogers Clark in 1782, Jefferson pulled even fewer punches: “Who he is you will probably have heard, or may know him by this description as being all tongue without either head or heart. In the variety of his crooked schemes however, his interests may probably veer about so as to put it in your power to be useful to him; in which case he certainly will be your friend again if you want him.”
Henry and Madison shared a passion for constitutional law, with each man, in his own way, playing a pivotal role in the establishment of constitutional governance in the United States. For Henry, this would play out at the state level in his beloved Virginia, while Madison had far loftier goals in mind. Henry, working closely with his friend George Mason, was an influential member of the Fifth Virginia Convention, which not only declared the colony to be a free and independent state but also authored the first Constitution of Virginia and drafted the Virginia Declaration of Rights. Henry’s reward for his role in the push for independence, which he had supported far earlier than many of his contemporaries, was to be chosen as the very first governor of the newly established Commonwealth of Virginia. His successor in that office, much to his chagrin, was none other than Thomas Jefferson. It was here that Jefferson’s alliance and lifelong friendship with Madison, who was serving as a member of the governor’s Council of State, was forged. The battle lines between the three men had now been drawn.
Portrait of James Madison by John Vanderlyn, circa 1816.
The first shots were fired in 1783. Jefferson, along with Madison, had grown dissatisfied with the state constitution that Henry’s Fifth Virginia Convention had produced. The two men now spearheaded a movement to revise its text. Virginia’s 1776 constitution, as was typical at the time, limited suffrage to wealthy male landowners. This had the effect of concentrating political power among the southeastern aristocracy. Jefferson and Madison, despite being wealthy male landowners themselves, desired to extend the franchise, albeit only to a somewhat larger group of male taxpayers in good standing. But Henry was jealously protective of his commonwealth’s founding document. He proved more powerful and managed to outmaneuver his opponents to devastating effect, blocking their attempts at revision. Jefferson summed up his frustration in a letter to Madison: “While Mr. Henry lives, another bad constitution would be formed, and saddled forever on us. What we have to do I think is devoutly to pray for his death.”
Portrait of Patrick Henry by Thomas Sully, circa 1851.
As Henry began focusing his attention inward, consolidating the stranglehold over Virginia politics that would prove crucial to his later gerrymander, Madison was looking outward. Not content with mere independence from Great Britain, which had left the newly established nation decentralized and fragmented, Madison instead turned his efforts, as well as his not inconsiderable talents, toward the cause of greater union. He had also found himself further embroiled in the growing rivalry between Jefferson and Henry, whose most recent disagreement concerned the relationship between government and faith. Henry, although suspicious of state-sponsored religion, nevertheless desired to impose a religious tax in Virginia, the revenues of which individuals could direct toward the support of their church of choice. Jefferson, as he would later famously state in an 1802 letter to the Danbury Baptist Association, preferred “a wall of separation between church and state.”
The dispute came to a head in 1785. Henry attempted to take advantage of Jefferson’s absence while serving as minister to France to force his proposed tax through the state legislature. This time, however, his attempt ended up backfiring. As Jefferson pulled the political strings by letter from Paris, Madison managed to persuade the Virginia General Assembly to reject Henry’s church-financing tax. Jefferson’s church-state separation bill, which he had first proposed without success during his time as governor, was instead approved in its place. The degree of bad blood between the longtime political foes grew deeper still as the date of the Philadelphia convention approached in 1787.
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The first attempt at establishing constitutional governance for the newly independent states had not gone well. The Articles of Confederation, drafted between July 1776 and November 1777, and ratified by all thirteen states by March 1781, were based chiefly on the guiding principle of preserving state sovereignty and independence. As such, they created an extremely weak central government that proved itself staggeringly ineffective at dealing with the problems of a large and diverse nation. The Continental Congress had been given no independent authority to lay and collect taxes, forcing the fledgling national government to rely on the generosity of the states, loans from foreign governments, and the sale of western real estate to raise the revenues necessary to function. The new government also had no independent executive branch, instead conferring upon the leader of the legislature the title of president and creating a “committee of the states” to exercise national authority whenever they were not in session.
This arrangement suited Patrick Henry. His long-standing acrimony for the divine right to absolute power that had been lavished upon the British monarchy had fanned the flames of his revolutionary fervor. Indeed, Henry’s suspicion of the centralization of executive authority in the office of the president, which he saw as not only a step backward toward despotism but also a betrayal of those who fought and died in the Revolutionary War, would go on to form the cornerstone of his case in opposition to the ratification of the Constitution.
But for others, including Jefferson and Madison, the failure of the federal government to respond effectively to Shays’s Rebellion in 1787, which had to be put down by the Massachusetts state militia after Congress was unable to finance an armed response, was the final straw in this failed first experiment in governing the United States. As a delegate to the Annapolis Convention in 1786, Madison joined with Alexander Hamilton in calling for a constitutional convention to consider amendments to the Articles of Confederation. Having failed to make his case in that forum, he sought election to the Continental Congress the following year, and this time was successful in persuading his fellow legislators to authorize the Philadelphia convention.
The question of who would represent the Commonwealth of Virginia as delegates to the convention, whose original mandate was limited only to the consideration of amendments to the existing constitution, was a thorny one. Madison, who had led the call for reform, was an obvious choice. And he was joined by a retired Revolutionary War general by the name of George Washington. Washington, despite supporting Madison’s case for a stronger union, had initially declined the assignment, citing concerns over the legality of the proceedings. But after an intervention by Madison and Virginia’s governor, Edmund Randolph, who would also serve as a delegate, Washington reluctantly agreed, although he made it clear that he was attending under duress.
Notably absent from the delegate list were the names of Thomas Jefferson and Patrick Henry. Jefferson was still in Paris, where he was joined in 1787, five years after the untimely death of his wife, Martha, by a fourteen-year-old slave from Monticello named Sally Hemings, who worked as a domestic servant and maid in the Jefferson household. Rumors of Jefferson’s ongoing sexual relationship with Hemings, which resulted in his fathering at least six of her children, first surfaced during his presidency in 1802.
The journalist James T. Callender, a former Jefferson ally who had become disaffected with his administration after failing to secure an appointment as postmaster, wrote in the Richmond Recorder, “It is well known that the man, whom it delighteth the people to honor, keeps, and for many years past has kept, as his concubine, one of his own slaves.” The story was picked up by numerous other papers, particularly those affiliated with his Federalist opponents. Jefferson never responded publicly to the rumors, although some interpret an 1805 letter to Secretary of the Navy Robert Smith as alluding to at least a tacit denial of the allegations. DNA evidence released in 1998 would prove definitively the link between the male-line Jefferson and Hemings descendants, and most historians now accept their relationship as established fact.
While Jefferson was not physically present in Philadelphia that summer, he continued to influence events from afar through another of his signature letter-writing campaigns. Henry, however, while offered a spot as delegate by Governor Randolph, declined the appointment. In another pithy declaration that may or may not be apocryphal, he opined that he “smelt a rat in Philadelphia, tending towards monarchy.” As Madison was carving out the leadership role at the convention that would see him forever immortalized as the “Father of the Constitution,” Henry watched anxiously, convinced that the delegates would use their mandate to debate proposed amendments to the Articles of Confederation as a pretext for ditching them entirely, to be replaced with a system that gave greater power to the central government. His fears did not prove to be unfounded.
But it was not until after the convention ended, during the debates over the ratification of the document that Madison had played a key role, perhaps more so than any other delegate, in drafting, that the long-running feud between him and Henry reached its apex, culminating in the infamous gerrymander of 1788. Henry, always the skeptic of concentrated federal power and defender of state sovereignty and individual rights, opposed the Constitution from the very beginning. “I have to lament that I cannot bring my mind to accord with the proposed constitution,” he wrote to George Washington shortly after the convention. “The concern I feel on this account is really greater than I am able to express.” Both Henry and his ally George Mason, with whom he had collaborated on the drafting of the Constitution of Virginia, emerged as key Anti-Federalist voices as the ratification debates heated up.
Madison meanwhile, along with two other leading Federalists, John Jay and Alexander Hamilton, took their case to the American people. They launched in the form of the Federalist Papers a passionate defense of the document they had produced at Philadelphia. It was a product of compromise to be certain, and bearing with it all of the imperfections, concessions, and trade-offs that had been necessary to forge agreement. But it was also a product of urgency. “We have seen the necessity of the Union,” wrote Madison in Federalist 14, “as the only substitute for those military establishments which have subverted the liberties of the Old World, and as the proper antidote for the diseases of faction, which have proved fatal to other popular governments, and of which alarming symptoms have been betrayed by our own.”
By the end of May 1788, South Carolina became the eighth state to ratify the Constitution, one short of the nine that were required for it to go into effect. All eyes turned to Virginia, which was scheduled to hold its ratification convention in Richmond that June. It was the last stand for Patrick Henry’s rapidly crumbling Anti-Federalist cause.
“Even more than the Lincoln-Douglas debate over slavery, or the Darrow-Bryan debate over evolution,” wrote the influential historian Joseph Ellis in his book American Creation, “the Henry-Madison debate in June of 1788 can lay plausible claim to being the most consequential debate in American history.” For almost four weeks the 168 delegates to the Virginia Ratifying Convention gathered in the sweltering heat of the Richmond Theatre to decide upon the future of the nation. There was no doubt who the stars of the show were going to be. According to contemporaneous transcripts, Henry spoke for almost a quarter of the entire proceeding. He was described by one delegate as “rising on the wings of the tempest, to seize upon the artillery of heaven, and direct its fiercest thunders against the heads of his adversaries.” Madison, ill throughout most of the convention, by contrast spoke so softly that the stenographer often had difficulty making out what he was saying. “He held his hat in one hand,” writes Ellis, “which contained notes he consulted like a professor delivering an academic lecture. But as a result his arguments arrived without flourish or affectation, in a sense the more impressive because of their austerity.”
What Madison lacked in oratorical brio, he made up for in keen, calculated political strategizing. Realizing that the vast majority of those in attendance had already made up their minds, he set to work persuading the undecided delegates behind the scenes. His number one target was Edmund Randolph, the seventh governor of Virginia. Randolph had been one of only three delegates to the earlier Constitutional Convention in Philadelphia, along with Elbridge Gerry and George Mason, who had voted against that initial ratification. Figuring Henry and his allies to be a lost cause, Madison gambled that if Randolph could be brought into the fold, the remaining undecided delegates would swiftly follow.
Over the course of a long series of correspondence, he finally wore Randolph down. He persuaded the governor to abandon his sticking point of conditioning ratification upon the passage of amendments to protect individual liberty, and instead vote to approve the Constitution as written. Madison’s commitment to introducing a bill of rights during the First Congress after ratification, amendments to the Constitution that would protect citizens’ individual liberties against the power of the federal government, ultimately proved decisive in his appeal. Randolph and the other wavering attendees were on board.
In a last desperate gambit, Henry seized upon Randolph’s now abandoned position, attempting to muddy the waters in what Madison derided as “a tactical ploy designed to confuse the undecided delegates.” In his final address to the convention, in which he proposed no fewer than forty separate amendments as binding conditions upon ratification, Henry extended his appeal to the heavens. “I see beings of a higher order, anxious concerning our decision,” he warned the assembled delegates as a thunderstorm appropriately began to rage outside the auditorium. “When I see beyond the horizon that binds human eyes, and look at the final consummation of all human things,…I am led to believe that much of the account on one side or the other will depend on what we now decide.” But it was all ultimately in vain. The next day, June 25, 1788, the convention voted 89–79 in favor of ratification. “Mr. Henry had without doubt the greatest power to persuade,” wrote John Marshall, the influential Federalist who would later become chief justice of the United States, but “Mr. Madison had the greatest power to convince.”
As it turned out, the support of the nation’s largest and most powerful state, although a major PR victory for the Federalist cause, proved largely irrelevant to the fate of the founding document under consideration that summer in Richmond. Four days earlier, New Hampshire had become the ninth state to complete the ratification process, ensuring once and for all that the Constitution of the United States would go fully into effect the following year. Nevertheless, for Patrick Henry, the defeat still stung. For those keeping score at home, the Henry-Madison rivalry was becoming a rather lopsided one. Despite successfully defending the Virginia Constitution against Jefferson’s designs on amendment to expand voting rights, Henry had lost the battle over church and state; failed to defend the Articles of Confederation—of which by 1787 he might have been the only remaining supporter—against what he believed was the hijacking of the Philadelphia convention by a faction bent on sowing the seeds of its destruction; and had now lost a similar constitutional holding action to Madison at the convention in Richmond.
But Henry was not quite ready to give up just yet. While he had failed to prevent the Constitution from being ratified, he still commanded a great deal of authority in his native Virginia. In particular, the general assembly, which under the quasi-parliamentary system in place at the time also had the power to select the governor, was still dominated by his Anti-Federalist allies. George Washington was acutely aware of the influence that Henry still retained over the commonwealth’s politics. In a letter to Madison from Mount Vernon, he wrote, “The Edicts of Mr. H[enry] are enregistered with less opposition by the Majority of that body, than those of the Grand Monarch are in the Parliaments of France. He has only to say Let this be Law—and it is Law.” And, when the members convened later in 1787 to determine who would represent the state in the newly created U.S. Senate, as well as how their U.S. representatives and federal electors would be chosen, Henry sensed an opportunity to even the score with his old political adversary.
First, he unveiled his plan for a second constitutional convention, persuading the assembly to pass a resolution calling for other states to support him in that effort. The U.S. Constitution, he argued, was a good starting point for creating a government that followed through on the revolution’s promise of liberty and state sovereignty, but it was still in need of a drastic overhaul. The forty amendments that he had proposed at the Richmond convention were no longer sufficient for fixing the broken document; what was required was a return to the drawing board, a fresh start to follow through on what had been promised at Lexington and Concord.
Under Article V of the Constitution, a new convention may be called upon the petition of two-thirds of the states. With New York heeding Henry’s call and passing its own resolution endorsing a second convention, there appeared to be some initial momentum behind his proposal. But preventing Madison from quashing that momentum by following through on his promise to introduce a bill of rights before the First Congress was crucial to the plan. While Henry certainly desired to protect civil liberties, he was more concerned with blunting the power of the federal government vis-à-vis the states. Persuading enough state legislatures to support an Article V convention would only be possible if he could bring the civil libertarians into the fold, and Madison’s proposal threatened to short-circuit that appeal.
At the request of George Washington, Madison threw his hat into the ring as a candidate to be one of Virginia’s two U.S. senators, although his correspondence reveals that the House of Representatives was his preferred appointment. But Henry would stop at nothing to prevent him from making it to Congress. Taking to the floor of the assembly during the debate over the Senate nominations, ostensibly to express his support for the two Anti-Federalist candidates, Richard Henry Lee and William Grayson, Henry went on to impugn Madison in a vicious personal attack. As one delegate recalled it in a letter to Madison, “Mr. Henry on the floor exclaimed against your political character & pronounced you unworthy of the confidence of the people in the station of Senator, that your election would terminate in producing rivulets of blood throughout the land.”
And thus it was law: the final vote was Lee 98, Grayson 86, and Madison 77—an ignominious defeat for one of the state’s most famous politicians. So far, at least, everything was going according to plan for Patrick Henry. Reflecting on the loss, Madison, unaccustomed to the sting of defeat at the hands of his rival, wrote to Jefferson that he had been “defeated by Mr. Henry who is omnipotent in the present legislature and who added to the expedients common on such occasions, a public philippic against my federal principles.” Having failed to secure election to the Senate, Madison turned to the only other avenue available to him if he were to realize his promise of a bill of rights: the upcoming elections to the U.S. House of Representatives. Before a year had passed, for the only time in U.S. history, two future presidents would face off for a single seat in Congress.
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The long-running enmity between Henry and the Jefferson-Madison alliance had by this point gone beyond a case of mere political disagreement: it was also personal. Jefferson, for his part, held Henry in extremely low professional regard, believing him to be arrogant, lazy, “insatiable in money,” and unqualified for most of the positions that he had occupied during his career. On Henry’s refusal to accept the position of secretary of state in George Washington’s cabinet, Jefferson remarked that “his self-esteem had never suffered him to act as second to any man on earth.” Madison took particular umbrage at what he saw as Henry’s duplicitous rhetoric during the Virginia Ratifying Convention, characterizing his remarks as “ill-founded” and “distorting the natural construction of language.” Henry’s motives are a little harder to read, given his preference for oratory over the written word. In fact, the entire archive of his papers from the Revolutionary War until his death in 1799 amounts to a meager 104 pages and sheds little light on the source of his very public vendetta. In any case, it was Henry’s actions that spoke louder than any words.
After leaving the governor’s mansion in 1786, Henry had returned to his seat in the Virginia House of Delegates, a position that gave him significant influence over the workings of the General Assembly. His plan to use gerrymandering to deny Madison a seat in the First Congress had four components. First, he would draw a district that packed in as many Anti-Federalist majority counties as possible along with Madison’s home county of Orange. Second, he would pass a law requiring all congressional candidates to be a resident of the district in which they were running. Third, he would persuade the legislature to appoint Madison as a delegate to the lame-duck Confederation Congress, forcing him to travel back and forth to New York when he should have been campaigning. And fourth, he would recruit the biggest political name he could find to run against Madison in the newly gerrymandered district. It was a testament to Madison’s ability, reputation, and overall star power that despite all four stages of Henry’s plan apparently coming off without a hitch, Madison still managed to win the election in a near landslide.
After dispensing with the selection of the state’s two U.S. senators in October 1788, the general assembly turned its attention the next month to the question of the House. Having decided to divide the state into ten districts, the delegates assigned the responsibility of drawing up a new electoral map for the 1789 elections to a subcommittee consisting of seven Federalists and eight Anti-Federalists.
According to a letter by George Mason, a bipartisan compromise emerged to divide the state “into ten districts, as nearly equal as Circumstances will admit; the Rule of Computation being the Number of Militia in each County.” And while the initial bill reported out of the committee was described in contemporaneous accounts as being somewhat beneficial to the Federalists, it was amended at least three times before final passage, twice in the House and once in the Senate. According to Madison’s sources in Richmond, as proceedings unfolded, “men of both factions…reported that Henry and his followers were amending the bill to help the electoral prospects of the Anti-Federalists.” One of the strongest pieces of evidence for the existence of a plan to gerrymander the districts comes from the papers of George Washington. He wrote to Benjamin Lincoln on November 14, “It is now much dreaded…that the State (which is to be divided into districts for the appointment of Representatives to Congress) will be so arranged as to place a large proportion of those who are called Antifederalists in that Station.”
Madison himself also appeared to be aware of the plan. Henry Lee wrote to him on November 19 stating, “Mr. H[enry] is absolute, & every measure succeeds, which menaces the existence of the govt.—the districts will be laid off, to conform to the antifederal interest.” Lest there be any confusion as to what exactly Lee was referring to, he clarifies later in the same correspondence: “I profess myself pleased with your exclusion from the senate & I wish it may so happen in the lower house—then you will be left qualified to take part in the administration, which is the place proper for you.” Even George Mason, perhaps Henry’s closest ally in the state, makes an oblique reference to the scheme in his correspondence, quoting an unnamed Anti-Federalist member of the assembly who states, after discussing the details of the House districting bill, that “the Feds have swallowed [it] like Wormwood.”
While no records survive of the details of the original districting plan drafted by the committee, or of the amendments offered by Henry and his allies, the final electoral map enacted into law by the general assembly on November 20 certainly bore the imprimatur of partisan manipulation. Or at the very least, of a personal crusade against one man. What drew particular ire from the observers at Mount Vernon was District 5. At first look, it bears little resemblance to either the famous salamander in Massachusetts or the contorted straits, rivulets, and appendages of the districts that form the poster children for the excesses of modern gerrymandering.
It was both compact and not significantly malapportioned, at least to the extent possible at the time, because the assembly endeavored to roughly equalize the number of militiamen between districts, figuring this to be a rough proxy for the number of eligible voters who resided there. But beneath the surface of District 5 lurks a far more sinister intent. In the district’s center sits Orange County, home to James Madison’s sprawling Montpelier plantation. Joining Orange in the district are seven additional Virginia counties: Amherst, Albemarle, Culpeper, and Louisa, as well as the quirkily named Fluvanna, Goochland, and Spotsylvania.
Map of Virginia’s Fifth Congressional District, 1788.
Spotsylvania County also happened to be home to James Monroe, with whom Madison maintained a friendship despite their finding themselves on opposite sides of most of the contentious political issues of the day. Monroe had been a fellow delegate to the Richmond convention, where, much to Madison’s annoyance, he had joined Patrick Henry in voting against ratification. The inclusion of Spotsylvania in Madison’s district was not an accident. The remaining counties in the district were chosen for one very specific reason: five of the seven had sent a slate of delegates to the Virginia Ratifying Convention that voted unanimously against the Constitution. As an analysis by the political scientist Thomas Rogers Hunter points out, “Of the sixteen delegates from what would become the Fifth District, eleven had opposed the new Constitution.” That the political leanings of an entire county could be inferred from the identities of the men who represented it seems an almost comically weak basis by today’s standards for crafting a gerrymander. But Henry did not enjoy the benefits of big data that allowed the creators of REDMAP to be so successful. Working with the limited tools at their disposal, the Anti-Federalists in the Virginia General Assembly drew Madison’s home county into a district that contained as many of the surrounding areas as possible that, based on their best guess, he might find electorally challenging.
Evidence for the intent behind Henry’s gerrymander can be found in the correspondence between Madison and his allies at the time. The first word of a possible plot being afoot comes from Edmund Randolph, who wrote to Madison on November 9, “The faction is, I am told, endeavoring to arrange the districts for representatives, so as to place Orange, to be counterpoised.” That same day, George Lee Turberville makes mention in his correspondence of an attempt “to obtain by finesse—what they could not accomplish—by fair & argumentative discussion.” Three days later, he elaborates further: “The prevalence of local prejudices are not uncommon in our house—but for a majority to bend its utmost efforts against an individual is rather uncommon—The object of the majority of today has been to prevent your Election in the house of Representatives as demonstratively as if they had affirmed it…by forming a district (as they supposed) of Counties most tainted with antifederalism in which Orange is included.”
On November 23, Edward Pendleton, after discussing Madison’s exclusion from the Senate on a party-line vote, goes on to note that the Anti-Federalists “are so modeling the Districts for choice of Representatives to the other House, as to have those Elections turn on the same basis.” Madison himself had not been present in Richmond for any of these events. He was now in exile in New York, appointed by the general assembly, at Henry’s insistence, to serve in a lame-duck legislature that would cease to exist when the U.S. Congress met for the first time in March 1789. With the elections for the House of Representatives scheduled for February 2, it’s hard not to see this move as a calculated attempt to remove Madison from Virginia, not only to prevent him from interfering with Henry’s legislative skulduggery, but also to keep him off the campaign trail in the run-up to the vote. Turberville surmised as much, writing to Madison, “I do verily believe that Mr. Henry Voted for you to [the Confederation] Congress this time with no other view but to keep you from [our] country until some more favored man, some minion of his or his party shall have the opportunity to supplant your Interest.”
For Henry’s plan to succeed, however, Madison had to seek election to Congress in the Fifth District, rather than somewhere else in the state where he might face an electorate more sympathetic to his Federalist principles. There was certainly no shortage of options. Of the ten districts that were ultimately drawn, six returned Federalist candidates to Congress who ran unopposed in the 1789 election. To prevent this possibility, Henry used his political clout in the general assembly to pass another law, one that required all candidates for federal office to have resided in the district in which they were running for at least twelve months prior to the election. “I am inclined to think that the Antis inserted this with a view to you,” reported one Federalist in a letter to Madison shortly after the bill passed, “and that the feds have assented to it from feeling their inferiority.”
Those familiar with constitutional law will immediately recognize that this restriction almost certainly violated the Constitution. In a 1995 case called U.S. Term Limits v. Thornton, the U.S. Supreme Court ruled that states may not impose any additional qualifications on prospective members of Congress beyond those which are found in the qualifications clause of Article I. To do so, wrote Justice John Paul Stevens for the majority, would “violate a[n]…idea central to this basic principle: that the right to choose representatives belongs not to the States, but to the people.” While this case, decided some 207 years after the fact, obviously did not bind as precedent the members of the Virginia General Assembly, those present at the time raised similar constitutional objections to the bill.
Edward Carrington, a close friend of George Washington’s who had served under the general during the Revolutionary War, was one of those who lobbied Madison to defy Henry’s residency restriction and seek office in another district. “This will be against the Act concerning the Elections,” he wrote to Madison on December 2, “but these gentlemen and many others are of the opinion that such a restriction was not within the power of the Legislature, and that it will avail nothing in Congress, where the qualifications of Members are to be judged.” But Madison would not be cowed. Unsavory as he found the notion of campaigning in his home county, the thought of being painted as a carpetbagger running scared from Henry was even worse. And he was now beginning to face pressure from his Federalist allies to throw himself into the fray.
Madison found himself in no-man’s-land, physically as well as mentally. He had left New York during a break in the Confederation Congress, traveling to Philadelphia to mull over the decision. “I came to this City with a view either to return to New York or proceed to Virginia as circumstances might require,” he lamented in a December 2 letter to George Washington. “I am pressed much on several quarters to try the effect of presence on the district into which I fall, for electing a Representative,” he continued, “and am apprehensive that an omission of that expedient, may eventually expose me to blame. At the same time, I have an extreme distaste to steps having an electioneering appearance, although they should lead to an appointment in which I am disposed to serve the public.” Torn between returning to New York to fulfill his duties to the Confederation Congress and the prospect of a potentially humiliating campaign in Virginia that might easily end in his defeat, Madison chose Virginia, lame-duck Congress be damned. Henry, however, had one last surprise waiting for him there.
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James Monroe was an obvious choice when evaluating candidates to recruit to run against James Madison in the Fifth District. As a resident of Spotsylvania, adjacent to Madison’s home county of Orange, he could be drawn into the district without any great difficulty. His preexisting friendship with Madison also made him immune to accusations of being a Henry crony. Monroe was the son of a modestly successful planter and sometime carpenter, and his family had immigrated to the United States in the mid-seventeenth century from Scotland, where they had been members of the ancient and respected Clan Munro. He grew up with politics in his blood. When his father passed away in 1774, his maternal uncle, a member of the Virginia House of Burgesses and later a fellow delegate of Patrick Henry’s at the Fifth Virginia Convention, took him to Williamsburg and enrolled him at the College of William and Mary.
Monroe was also a war hero, having dropped out a year and a half into his studies to enlist in the Third Virginia Regiment of the Continental army. Cited for bravery personally by George Washington, after he suffered a severed artery and almost died during the crossing of the Delaware River, he rose swiftly to the rank of colonel, although financial difficulties would prevent him from being able to raise his own regiment.
Portrait of James Monroe by James Herring, circa 1834.
Eventually returning to Williamsburg to study law, he became a protégé of the then governor, Thomas Jefferson, served as a member of the Virginia House of Delegates and the Confederation Congress, and, as already mentioned, became one of the seventy-nine delegates to vote against the Constitution at the Virginia Ratifying Convention. Even before Monroe had been drafted into his scheme, Henry had already been laying the groundwork for the campaign against Madison. His strategy, which dovetailed neatly with his broader goal of forcing a second constitutional convention to undermine the Union, was to paint Madison as an ideologue, a fanatical supporter of the Constitution as written whose myopia made him oblivious to the many flaws in the document that Henry and the Anti-Federalists believed might be addressed by a second convention. Upon returning to Virginia, Madison was shocked to discover that “it has been very industriously inculcated that I am dogmatically attached to the Constitution in every clause, syllable & letter, and therefore not a single amendment will be promoted by my vote, either from conviction or a spirit of accommodation. This is the report most likely to affect the election, and most difficult to be combated with success, within the limited period.”
But combat it he did. While his pride might have made him queasy about the prospect of grubbing for votes on the streets of Orange, Madison proved himself a natural on the campaign trail. There’s little doubt that he was aware of Henry’s designs on a second constitutional convention, because those arguments had been aired extensively during their 1788 debates in Richmond. He must also have known that if he were able to follow through on the promise he had made privately to Randolph and others to introduce a bill of rights before the First Congress, this would surely take the wind out of Henry’s sails once and for all. From this perspective then, Madison’s strategy for defeating Monroe was a stroke of genius. Having denied the necessity of a bill of rights during the Philadelphia convention, and only grudgingly promising it to Randolph during their backroom dealings in Richmond, Madison now embraced it publicly. Channeling the spirit of his mentor Jefferson, he embarked on a prolific letter-writing campaign, including several that were published in local newspapers. He weaponized Henry’s own arguments against him, making the case for amending the Constitution to protect individual liberties.
“The offer of my services to the district, rests on the following ground,” Madison wrote to a resident of Spotsylvania County a week before Election Day. “That although I always conceived the constitution might be improved…I held it my duty, whilst the constitution remained unratified, and it was necessary to unite the various opinions, interests and prejudices of the different states, in some one plan, to oppose every previous amendment.” So far, this was all in keeping with his prior public statements. “The change of circumstances produced by the secure establishment of the plan proposed,” he continued, “leaves me free to espouse such amendments as will, in the most satisfactory manner, guard essential rights, and will render certain vexatious abuses of power impossible.” And, in what appeared to be a not-so-subtle dig at Henry himself, he concluded, “With regard to the mode of obtaining amendments, I have not withheld my opinion that they ought to be recommended by the first Congress, rather than be pursued by way of a General Convention.”
A more cynical opponent might have used this opportunity to go on the offensive, painting Madison as a disingenuous opportunist who changed his positions whenever it was politically advantageous to do so. After all, how could he be trusted to vote for the Bill of Rights when he had already voted against it? But James Monroe was not such an opponent. Both men ran extremely positive campaigns, often traveling together and making joint appearances around the district. Their friendship and mutual respect would allow them to attack each other’s principles and policy positions but never their characters.
The biographer William Cabell Rives describes one particular debate that Madison remembered for the rest of his life. On a frigid January morning in Culpeper County, the two men faced off on the portico of a Lutheran meetinghouse. Keenly aware that his election would depend on the ability to court the votes of religious minorities in the district, which contained not only Lutherans but also a significant Baptist population, Madison took the opportunity to espouse his views on religious freedom. He also made sure to remind his constituents of the church tax Henry had proposed years earlier, and his own role in defeating it in the legislature. “Such was the extremity of the cold,” writes Rives, “that Mr. Madison’s ear was slightly frost-bitten while speaking. Some traces of the injury always remained; and he would playfully point to them as the honorable scars he had borne from the battle-field.”
As Election Day approached, all the momentum seemed to be with Madison. Even the weather would not be able to stand in his way. As temperatures dropped to ten degrees below zero, and almost a foot of snow blanketed the ground, the voters of Virginia’s Fifth Congressional District made their way to the polls. When the returns were in, Madison was victorious, and the election was not even a particularly close one. He won 1,308 votes to Monroe’s 972, good for a 57–43 percent majority. While the candidates split the eight counties in the district four to four, the key to Madison’s victory was to bolster the lopsided margin in his home county of Orange, where he captured 96 percent of the vote, with surprisingly strong performances in the surrounding Anti-Federalist areas. This included 38 percent of the vote in Monroe’s home county of Spotsylvania, and losses by a single vote in Goochland and 21 votes in Fluvanna, both considered Anti-Federalist strongholds. Finally, in Culpeper, the county that had been considered pivotal to the outcome and in which the candidates had campaigned extensively, Madison ran riot, winning 71 percent of the vote. Henry’s plan had failed.
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There’s one small problem with this tale of Patrick Henry’s underhanded scheme to thwart his archrival’s effort to rally the country in support of the fledgling Constitution that he so despised: it might never have happened. Historians are divided as to whether Henry, though clearly not acting in Madison’s best interests, actually intended to manipulate the district boundaries in an effort to keep him out of Congress. And even if the gerrymander was intentional, there is also significant disagreement as to whether it was part of some master plan to undermine the Constitution and precipitate a second convention, or merely the petty settling of a political score.
Skeptics of the gerrymander point out that the only contemporaneous sources for the allegation come in the form of accusations from persons at Mount Vernon, including George Washington, insinuations by Madison himself, a few statements made by Anti-Federalist allies of Henry before the fact, and partisan newspaper coverage afterward. None of Henry’s own writings, sparse as they are, make any reference to a plan to use gerrymandering against Madison, nor do the statements of any of the legislators who were directly involved in drawing up the districting plan. Of course, none of this means that it didn’t happen, and Madison himself clearly believed that he had been the victim of something untoward.
Critics of the Henrymander narrative also argue that the nature of the districting plan itself cautions against its depiction as an intentional gerrymander. Elmer Griffith, in his famous 1907 dissertation on the history of the gerrymander, maintains that “the charge that the state was gerrymandered is unwarranted, and as concerns Madison’s district in shape and population it was normal.” And, in the most comprehensive recent analysis of the events, the political scientist Thomas Rogers Hunter reaches a similar conclusion. He contends that “Virginia’s entire 1788 districting scheme shows no marks of partisan purpose, for it was both politically fair and one of the most geographically logical plans in all of American history.” He credits the origins of the Henrymander narrative to the aforementioned Madison biographer William Cabell Rives. An associate of both Madison and Jefferson, Rives had written in the 1850s that “in laying off the State into districts for the election of representatives, ingenious and artificial combinations were resorted to for the purpose of insuring [Madison’s] defeat.”
But as both Griffith and Hunter correctly point out, Henry’s plan did nothing of the sort. Madison’s district was geographically compact, followed existing geographic and municipal boundaries, and was roughly equal in population to those in other parts of the state. Rives’s source appears to be the writings of an anonymous columnist in The Virginia Independent Chronicle, who published twenty-three letters between January and July 1789 under the pseudonym Decius. “I call it an attempt to deprive the people of their choice of a Representative,” Decius wrote in a February 23 column, “because the very idea of its being necessary to form a district in any particular way, to affect the election of any one, is sufficient evidence that the decision intended is contrary to the inclinations of the natural majority to be affected; and an attempt to form it so, is only in other words, to deny them the right of choosing for themselves.” But pushed to defend his accusations by an Anti-Federalist reader, Decius appeared to backtrack on his earlier accusations. He subsequently clarifies that he was merely objecting to the “eccentric angles” of an earlier proposed version of the district that also included parts of Cumberland County, rather than its eventual form.
It’s certainly true that Cumberland, which gave 81 percent of its votes to the Anti-Federalist candidate in the 1789 election, could easily have been substituted for Culpeper. This, along with the inclusion of adjacent Buckingham County, would have produced a district much more likely to bring about Madison’s defeat. But none of this information was known to Henry and his allies in 1788. The most straightforward explanation of the available evidence is that Henry, constrained by a dearth of data and a desire to avoid losing his eroding majority in the general assembly—which Carrington describes as being “reduced to about ten at the completion of his projects”—cobbled together the best attempt he could muster under the circumstances to make things as difficult as he possibly could for Madison. The fact that the gerrymander was unsuccessful does not, in and of itself, mean that it wasn’t a gerrymander. It certainly seems plausible that Henry originally envisioned a district that would have been more hostile to Madison, but was forced to compromise somewhat as the bill was amended before final passage. Barring the discovery of firsthand accounts of the legislative proceedings, we may ultimately never know for sure.
What cannot be disputed is that the circumstantial evidence does support the notion of a deliberate scheme on Henry’s part. Why pass a law requiring candidates to reside in the districts in which they were running if not to force Madison to contest an election on hostile turf? Why draw Madison’s and Monroe’s home counties into the same district if not to force the two men to compete against each other? Why appoint Madison to the Continental Congress when he clearly had no desire for the job? It’s hard to put these pieces of the puzzle together and not, as Henry himself had done only a year earlier, smell a rat in Richmond, tending toward chicanery. The Republicans in Wisconsin would have behooved themselves to take a page from Patrick Henry’s book, and not leave such a detailed paper trail laying out the particulars of their conspiracy.
The postscript to this story is, of course, well known. Henry’s plan to force a second constitutional convention, part of his broader effort to undermine the newly established American system of government, went down in flames. When the First Congress met at Federal Hall in New York on March 4, 1789, Madison had done his homework. He arrived armed with a slate of proposed amendments that would safeguard individual liberty. These, he hoped, as outlined in a letter to Jefferson, would “give to the Government its due popularity and stability.” Faced with the prospect of the undoing of the fragile compromise of 1787, and the possible dissolution of the federal government, the representatives of the First Congress got to work. After many months of debate, revision, and compromise, what emerged were ten proposed constitutional amendments that today form the cornerstone of American liberty: the Bill of Rights. Freedom of speech, freedom of religion, the right to bear arms, the right to assembly, and all the other protections that we take for granted were only made possible because Patrick Henry’s plan failed.
In his twilight years, Henry became somewhat more sanguine when reflecting on his earlier jeremiad against the Constitution. Gone were the soaring rhetorical declarations of his rabble-rousing days as a revolutionary, replaced with grudging acceptance of his defeat, if not outright contrition. “Although the form of government into which my countrymen determined to place themselves had my enmity,” he wrote to Monroe in 1791, “yet as we are one and all embarked, it is natural to care for the crazy machine, at least so long as we are out of sight of a port to refit.” So complete was his about-face that Washington even offered him the position of secretary of state in 1795, but Henry declined, citing failing health and the financial burden of providing for his children, of which he had seventeen by two different wives. Or perhaps it was the prospect of succeeding two of the men who had played a pivotal role in thwarting his life’s ambitions, Thomas Jefferson and Edmund Randolph, America’s first and second secretaries of state.
Returning to the practice of law, Henry died of stomach cancer in 1799 at his home in Red Hill, Virginia. Even death could not spare him one final parting shot from his old adversary. “A man who, through a long & active life, had been the idol of his country, beyond any one that ever lived,” Jefferson wrote in 1812, “descended to the grave with less than its indifference, and verified the saying of the philosopher, that no man must be called happy till he is dead.” Madison, by contrast, went on to succeed his mentor as the fourth president of the United States and to become one of its most famous and lauded citizens. So go the breaks.
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One thing that stands out about these early forerunners of the modern gerrymander is that they appear somewhat underwhelming when placed under the microscope of hindsight.
George Burrington marshaled every ounce of authority he possessed as the king’s representative in North Carolina to lash out against his detractors in the legislature, but the districts he created to secure a majority of his creatures in the lower house were more akin to the rotten boroughs of yore than anything that might be found in a modern legislature.
Henry certainly appears, based on the preponderance of historical evidence, to have at least attempted to use the redistricting process to settle a political score with his old foe James Madison, but he lacked the tools, and the political capital, to follow through with it effectively.
And poor Elbridge Gerry, who neither authored nor particularly supported the redistricting plan that created his infamy, suffered the ignominy of having his own name repeatedly mispronounced in the portmanteau that was his most lasting contribution to the world. If there’s one lesson to be drawn from this whistle-stop tour of colonial- and founding-era redistricting, it’s that the milquetoast gerrymanders of yesteryear, while certainly not lacking for intent, bear little or no resemblance in terms of their effects to the REDMAP-inspired atrocities that blight the landscape of contemporary America. Moving into the mid- to late nineteenth century, however, the gerrymander would become more sophisticated, efficient, and in some cases devastatingly effective.