On May 5, 1856, as described above, another pro-slavery judge, Judge Lecompte, convened a grand jury to issue warrants for treason against known free state men. A posse, consisting largely of Missourians, was recruited to execute the warrants and to intimidate the free state stronghold in Lawrence. Word spread that pro-slavery forces were massing for their second attack on Lawrence. The Pottawatomie Rifles assembled and began marching to the aid of their free state compatriots. Before the group could reach Lawrence, it was ransacked on May 21, 1856. When word reached the free state militia on May 22, the group halted in indecision and after a day or so most dispersed back to their homes.
All except Old John Brown and a band of followers. Upon hearing of the sack of Lawrence, Brown decided that some response was required. According to his son Jason, Brown said: “Now something must be done. We have got to defend our families and our neighbors as best we can. Something is going to be done now. We must show by actual work that there are two sides to this thing and that they cannot go on with impunity.” Exactly what it was that Brown intended should be done has been the subject of some dispute. Did he set out bent on killings? Or was his initial intention to capture a set of pro-slavery men with the intent of intimidating them or perhaps subjecting them to some sort of ad hoc “trial”? Brown’s apologists have made the latter claim. Whether it is supportable by the evidence may be an issue in the trial.
John Brown, Jr., who did not participate in the Pottawatomie Creek killings, seems to have been in little doubt. Of his father’s intentions before setting out, he said later said, “It was now and here resolved that they, their aiders and abettors, who sought to kill our suffering people, should themselves be killed, and in such manner as should be likely to cause a restraining fear.”
On May 23, 1856, John Brown, Sr. formed his group of avengers from among the men of the Pottawatomie Rifles. They included his sons Owen, Frederick, Salmon, and Oliver as well as Henry Thompson, James Townsley, and Theodore Weiner. Brown asked Townsley to take the group to Pottawatomie in his wagon, with Weiner riding alongside on his pony. Brown also invited James Hanway to come along, but Hanway refused. The group sharpened their swords, with a boy named Baine Fuller turning the grindstone for them. Fuller’s father requested that Brown keep his son out of any trouble that was brewing. Brown said that he would, and true to his word did not invite Fuller on the raid and made sure that the boy had a solid alibi for the night of May 24, 1856.
At or before the time that Brown was leading his small group away from the main body of Pottawatomie Rifles, they encountered a man named Gardner who, according to Salmon Brown, told them “the news of the assault upon Senator Sumner by Bully Brooks – carrying the message hidden in his boot. At that blow, the men went crazy – crazy. It seemed to be the finishing, decisive touch.”
When the men arrived at Dutch Henry’s Crossing, Brown asked Townsley to identify all of the pro-slavery men who lived along the Pottawatomie Creek. It was Brown’s intention to “sweep the creek” of all pro-slavery men living on it. Salmon Brown said they waited for darkness because John Brown feared they would not be able to “take the doomed men in daylight.” At 10:00 PM on May 24, the men set out for the Pottawatomie Creek.
Five men were murdered that night. Although all five were pro-slavery, none of them were slave owners themselves. The pro-slavery press described them all as “plain, honest, peaceable farming settlers.” The first killings were of John Doyle and his two sons, William and Drury, who lived at the mouth of Mosquito Creek where it empties into Pottawatomie Creek. Brown’s group spared Mrs. Doyle, their daughter, and their son John. A variety of reasons for selecting the Doyles have been suggested. First, William and Drury had been given the task of serving Judge Cato’s warrants. Second, it was said in the local community that “the old man and his two sons called on a man who kept store near Shermans – and told him to pack up his goods, move off his claim in 5 days or they would kill him.” The implication of this statement, though not spelled out by the writer (himself a free state man), is that the Doyles were among the pro-slavery men who were attempting to drive free staters out of the territory. Another source suggests that the elder Doyle “had his sons … keep free-state men from the polls by force.”
Next, the company moved down Mosquito Creek to the home of Allen Wilkinson. Wilkinson was the postmaster for Pottawatomie and also a member of pro-slavery territorial legislature. One source claims that Wilkinson acted as, in effect, the prosecuting attorney for Judge Cato’s court in considering the issuance of warrants for free state men (however, this claim seems doubtful). Descriptions of Wilkinson’s general character vary depending on which account one reads. A pro-slavery writer of the period describe him as a “quiet, inoffensive man.” A free state writer described him as a “very violent and imprudent man making threat of killing and burning,” whose wife “frequently urged him to be more quiet – but could not do it.” One of the men called inside to the Wilkinsons for directions, and asked them to step outside. Mrs. Wilkinson was deathly ill with measles, and begged John Brown to not take her husband because she needed him to care for her. Nonetheless, the Brown party took Mr. Wilkinson, marched him down the road, killed him, and threw his body into the brush on the side of the road. Townsley claimed that one of the younger Brown sons killed Wilkinson. Salmon Brown says Thompson and Weiner killed him. The company crossed Pottawatomie Creek and went to the house of “Dutch Henry” Sherman, a German settler.
At around 2:00 AM, Brown and his group discovered that Dutch Henry was gone, so they went to his neighbor’s, James Harris. They claimed that they were “the Northern Army” and when Harris opened the door, he saw three men standing there. Harris recognized John Sr. and his son Owen. The men entered the house and made prisoners of Harris and his guests, “Dutch” William Sherman (Dutch Henry Sherman’s brother), John Whiteman, and Jerome Glanville. The Brown company ransacked the house, stealing what provisions they could, and interrogated the men about their political affiliations. Harris, Whiteman, and Glanville gave the apparent “appropriate” response. Their lives were spared. But Dutch William Sherman was found the next morning with his skull split open in two places, a large hole cut in his breast and his left hand severed from his body. Perhaps he gave an inappropriate response. More probably, he was known to the Brown group before. According to a local free state settler writing shortly after the killings, “Sherman it is said has repeatedly threatened to shoot and exterminate free state men, and at the news of the fate of Lawrence raised a red flag; which was said he meant to intimate that war was commenced and he was in for it.” More particularly, Weiner identified both Shermans, and Dutch Bill in particular, as among the proslavery men who had come to his store and ordered him to leave the territory.
Townsley blamed Brown’s two youngest sons for killing Sherman, while others, including Salmon Brown, claimed Thompson and Weiner killed Sherman.
John Brown’s mission to “strike terror into the hearts of the Pro-Slavery party” and to kill those who “sought to kill our suffering people [the Free Staters]. . . should themselves be killed, and in such manner as should be likely to cause a restraining fear” was accomplished. According to Townsley, Brown insisted that Townsley take the company to more homes of pro-slavery settlers that night, but Townsley refused; he refused to engage in killing like that anymore.