Some of the men who joined the growing army in the Neutral Ground had experience at this game before. Seven years before, the first filibuster against New Spain started improbably when an American congressman asked the Spanish government to evict three Americans from his land in Spanish West Florida. The three men, brothers Reuben, Nathan, and Samuel Kemper, would become notorious in the borderlands and play crucial roles in two major attempts to seize Spanish territory. Late in 1812, Samuel Kemper assumed command of the Republican Army of the North on the death of Augustus Magee, leading it to victories at La Bahía and Rosillo.
The Kempers were descendants of German immigrants imported by Virginia’s Royal Governor Alexander Spotswood to work a coal mine on his property. Following the end of their indentured service, the immigrants settled in the northwestern reaches of the state, founding the town of Germanna in Fauquir County. The county soon developed a unique identity as a place of refuge for poor squatters and others who had a disregard for law enforcement, violation of liquor laws, and other transgressions, and was known as a “free state” for its spirit of opposition to the coast. Two second-generation brothers, Peter and James Kemper, fought in the American Revolution and were both ordained as Baptist ministers. After the war, the nearby frontier provinces called to James Kemper, who moved first to Kentucky, then to Ohio, where he became one of the founders of the city of Cincinnati. Peter soon followed, leaving two older sons in Virginia and bringing along the three sons, Reuben, Nathan and Samuel. Peter Kemper was well acquainted with another Baptist minister in the growing Ohio Territory, John Smith, who would soon be elected as one of the first U.S. senators from Ohio. Smith engaged in land speculation in Mississippi on the U.S. side of the border, and across the border in Spanish West Florida. Because Spanish law at the time frowned on absentee landowners, Smith engaged the eldest Kemper brother, Reuben, to occupy and manage his holdings. Nathan and Samuel (the youngest of the three) followed shortly thereafter.
Reuben Kemper worked hard in pursuit of his fortune, but a series of failures left him destitute. Furthermore, he believed his residence on Smith’s land entitled him to it, and soon he was fighting with his patron, who sued him and ordered the brothers removed from his lands. The spat soon grew into a feud between rival factions of Anglo Americans living in Spanish territory, with the Kempers siding with the pro-American settlers, while their opponents were generally loyal to Spain. Nonetheless, as William C. Davis remarks, “Nothing suggests that the Kempers had a fixed determination to foment rebellion or to call on their countrymen to rise against Spain…They were just angry and vengeful.” But their anger soon evolved and the divided loyalties began to give a political character to the feud.
In 1804, while Reuben was away in New Orleans, local officials moved on his house, hoping to seize it. Nathan, Samuel, and four other well-armed men barricaded themselves inside and Samuel threatened to fight. The officials backed down, but the feud ratcheted up. The Kempers and their loyalists began a tragic-comic rebellion that petered out with a failed attempt to seize Spanish leaders and declare a republic in West Florida. Withdrawing to the American side of the border, the Kempers plotted their next move, occasionally raiding into Spanish territory. This led to a violent response in 1805, when a lynch mob of Spanish citizens (of Anglo-American, not Spanish ancestry) crossed the border and seized the three brothers. At the time, Samuel was running a tavern in Pinkneyville, Mississippi. In one of a dozen court affidavits later recorded of the incident, a witness, James Latta, said the vigilantes came late at night to Kemper’s tavern painted black, poorly disguising themselves as runaway slaves. Once they were let inside, they then burst into his private room. Samuel Kemper’s own testimony provides further detail. At around midnight, Kemper heard a knocking on his door and challenged the other party:
The door of the bed room was then forced and a blow made at the bed with a double-barreled gun. [Kemper] was then seized, and dragged out of bed…and from thence after a struggle, into the street. He was then thrown on the ground, and a rope was tied around his neck, by which he was dragged about one hundred and fifty yards. He was then suffered to stand upright, and attempted, by crying out, to give an alarm, upon which he received a stroke of a pistol on the head, by which he was stunned.
At one time, up to five men were pummeling Samuel with clubs. Nathan, likewise, was pulled from his bed as his wife shrieked piteously before she was clubbed unconscious. Reuben received perhaps the worst beating, which many of the witnesses feared would be fatal. The Kempers were then tied and put aboard boats to cross into Spanish territory. They were only saved when an alerted U.S. Army patrol intervened and captured the Spaniards. Tried, they were eventually released on account of time served, and though the Kempers promised no further violence, Reuben assaulted the men as they left the courthouse. The filibuster was effectively over, but the bitterness remained.
The Kemper brothers’ motives once they turned the feud into a filibuster have long divided historians. Davis argues that Reuben Kemper’s rebellion was inevitable and that the feud only provided the spark. There was even speculation at the time that Reuben, far from seeking to win the province exclusively for America, was seeking British aid for an expedition to capture Spanish territory. Gene Allen Smith summarizes much of the literature thusly: “On the local level inhabitants seized power at Spain’s expense because they wanted an efficient, responsible local government to protect their rights, and because they hoped to acquire land and wealth.” Isaac Joslin Cox said the Kemper raid was “no mere act of bravado, but evidently a serious attempt to overthrow the existing government. However, McMichael is not so eager to elevate the Kempers’ motives, calling their actions “nothing more than random thuggery in response to an unfortunate lawsuit.” 
Nonetheless, for a brief time, the Kempers, men of little wealth or status, became famous throughout the country. Word of the assault in particular spread in the South and further encouraged American plotting against Spanish West Florida, not in the least because of the fact that some slaves had participated alongside their masters in the assault on the Kempers, which enraged many slave owners constantly in fear of a slave revolt. The attention drew scorn from some, praise from others and visits from mysterious suitors. In New Orleans, Samuel was approached by men affiliated with an organization known as the “Mexican Society of New Orleans.” He introduced them to Reuben and his older brother soon took an oath “to use all lawful means to aid and assist in effecting the emancipation of Mexico and Peru.” The men were brought into a conspiracy to raise arms and men for another attempt at rebellion in West Florida which would, they were told, then be extended to Texas. Reuben Kemper, however, was skeptical of the venture and began to fear that the plot was a continuation of the Burr conspiracy. He was opposed to any venture that involved separatism or would not be legally condoned by the U.S. government. He was also hostile to Burr all the more so because his former landlord and enemy, Smith, was close to the former vice president. One of the final straws came with the arrival of another emissary, a U.S. Army quartermaster and subordinate of Wilkinson named Josiah Taylor, with whom Reuben had a tense relationship. This is almost certainly the same Josiah Taylor who was later imprisoned in the Alamo and joined the Gutiérrez-Magee as a filibuster. The brothers cut ties with the group, which they did not think was serious. Nonetheless, when another, more successful filibuster attempt into West Florida was begun in 1810, Reuben and Nathan joined it. Samuel, for his part, moved on to run a tavern in Alexandria, Louisiana. But the brief encounter in New Orleans with the “Mexican Society” was not inconsequential, for among the men he met through the group was Gutiérrez, then on his trip northward to Washington to plead the case for the revolution in Mexico. When Gutiérrez returned, it was only natural that Samuel, a known frontier filibuster, hater of Spanish authority, and natural leader of men, would be one of his targeted converts.
The plots of the “Mexican Society” were enough to reach the ears of Spanish minister Luis de Onís y González-Vara, who wrote in 1812 that America (since he believed the government to be involved) had “a famous lawyer of New Orleans to contact the insurgents in Mexico and to offer them every kind of aid in money, arms and officers to make war on the troops of the king.” While a thorough analysis of the organization is beyond the scope of this study, the known organizers were elite interests generally more likely to pay for muskets to arm frontiersmen than actually take part in an expedition themselves. An exception was a leader of an offshoot, the “Mobile Society,” a controversial lawyer (charged in 1807 for barratry) named Joseph Pulaski Kennedy. It was Kennedy who had told Judge Toulmin that an attack on Spain was not a violation of the Neutrality Act because Spain was not recognized by the U.S. Kennedy led the second West Florida filibuster in 1810, and later joined the Gutiérrez-Magee Expedition.
Kennedy’s motives are murky because he clearly deceived others about his intentions. In one letter to a Spanish resident of Mobile who he hoped to convert to the cause, Kennedy appears to be a Burrite, promoting Western separatism, rather than American conquest of West Florida, as an aim: “As for the King of Spain, he is out of the question. Do you wish to become a free subject of the Emperor of France or of his brother Joseph, you have only to say so and it is done. The bearer of this will explain everything to you. If you are desirous of embarking in the cause of liberty and your noble country, make your arrangements with my friend.” But, in a letter to the Spanish commandant of Mobile, whom the Americans thought could be persuaded to join, rather than fight them, Kennedy took an entirely different tone:
As a member of the Mobille (sic) Society I can with certainty inform you that the citizens of these counties never will make an attack on that country without the concurrence of the general Government…. This Society has an origin in the oppression which we have suffered from the Spanish Government in detaining a country which the Supreme law of the State has declared to be ours. We respect the subjects of the King that was of Spain, and as to yourself, I have no difficulty in saying that you have my good wishes for your happiness.
The West Florida Controversy had different origins and purposes than the Gutiérrez-Magee Expedition, but the former clearly shows that remnants of the Burr conspiracy were still active in Louisiana and Mississippi into the 1810s, providing a ready ideology, source of funds and adherents that made for ground when Gutierrez traveled through the area in 1811 and planted the seeds of the expedition of the following year. Those seeds would grow, attracting veteran filibusters like Kemper, a lower-class border brawler, and Kennedy, a lawyer with elite pretentions. Though they came to the fight from different perspectives, Kemper and Kennedy were both very influential on the frontier and likely drew additional converts to join the cause in Texas when they joined. The army they were joining had grown large enough and was nearly ready to attack.
 Willis M. Kemper, Genealogy of the Kemper Family in the United States: Descendants of John Kemper of Virginia; with a Short Historical Sketch of His Family and of the German Reformed Colony at Germanna and Germantown, Va. (Germanna, Va.: G.K. Hazlett & Company, 1899), 10.
 James Kemper’s home still exists, and is preserved on the grounds of “Heritage Village” at the Cincinnati Zoo. http://www.heritagevillagecincinnati.org/kemper_house.aspx (Accessed March 12, 2016)
 Kemper, 50.
 West Florida at this time included parts of Eastern Louisiana, Southern Mississippi and Southern Alabama, while East Florida roughly consists of the borders of the present state. Smith was heavily involved in speculation and was even implicated in the Burr conspiracy.
 Andrew McMichael, Atlantic Loyalties: Americans in Spanish West Florida, 1785-1810 (Athens: University of Georgia Press, 2008), 83.
 William C. Davis, Rogue Republic: How Would-Be Patriots Waged the Shortest Revolution in American History (Boston: Houghton Mifflin Harcourt, 2011), 12.
 Ibid., 23.
 U.S. Department of State. State Papers and Publick Documents of the United States from the Accession of George Washington to the Presidency, Exhibiting a Complete View of Our Foreign Relations at That Time (Boston: T.B. Wait and Sons, 1817), 105-108.
 Davis, xiii, and Francis Cogliano, Failed Filibusters: The Kemper Rebellion, the Burr Conspiracy and Early American Expansion, 6. http://www.shca.ed.ac.uk/staff/supporting_files/fcogliano/failed-filibusters.pdf (Accessed March 12, 2016).
Gene Allen Smith, “Rogue Republic (Review),” The Alabama Review 65 no. 2 (April, 2012): 137.
 Isaac Joslin Cox, The West Florida Controversy, 1798-1813: A Study in American Diplomacy (Gloucester, Mass: Peter Smith, 1967), 155; McMichael, 88.
 Davis, 87.
 Davis, 89. While some sources suggest that Reuben Kemper also participated in the expedition, this is not the case, as Davis demonstrates.
 Warren, 22. The lawyer was probably James Workman, a judge. See Davis, 88.
 J.P. Kennedy to Z. Orso, 7 June 1810 and J.P. Kennedy to D. Perez, 19 July, 1810, In J. Franklin Jameson, ed. The American Historical Review Vol. II (New York: MacMillan Company, 1897), 700-701.