Brown was not a particularly good businessman, and what skills he had declined as his thinking became more metaphysical. He bought and sold several tanneries, engaged in land speculation, raised sheep, and established a brokerage for wool producers, but his financial situation deteriorated. His thoughts turned more and more to people he considered oppressed; had he lived in a later era, he might have become a socialist.
Often seeking the company of blacks, he even lived in a freedman's community in North Elba, New York, for two years. He became a conductor in the Underground Railroad and organized a self-protection league for freemen of color and fugitive slaves.
By the time he was 50 years old, Brown was convinced God had selected him as the champion to lead slaves into freedom, and if that required the use of force, well, that was God's will, too. After the Kansas-Nebraska Act of 1854 gave citizens of those two territories the right to choose for themselves whether the territories would permit or prohibit slavery, Brown, like many abolitionists, moved to Kansas, taking five of his sons with him. Fervent members of the abolition movement were determined that when the territory was ready to enter the Union as a state, it would do so as a free state. On the other side, many defenders of slavery were also pouring into Kansas, in order to secure it for the pro-slavery faction.
On May 21, 1856, Missouri "border ruffians" attacked the anti-slavery town of Lawrence, pillaging and burning. Two days later, Charles Sumner, a U.S. Senator from Massachusetts, was severely beaten with a cane on the Senate floor by Senator Preston Brooks of South Carolina because of verbal attacks the virulently anti-slavery Sumner had made on another South Carolinian.
Rumors spread that the border ruffians intended to attack the anti-slavery settlers on Pottawatomie Creek, Kansas; Brown and his family were among the abolitionists in this sharply divided area. On the night of May 24, Brown, with four of his sons and two other men, rode to the homes of three pro-slavery settlers near Dutch Henry's crossing on Pottawatomie Creek; Brown intended to "Sweep the Pottawatomie of all pro-slavery men living on it." They dragged James Doyle and two of his sons, William and Drury, from their farmhouse. When the trio tried to escape, James Doyle was shot down and his sons hacked to death with short sabers. Doyle's wife, daughter and 14-year-old son John were spared. At the home of Allen Wilkinson, the avengers ignored the pleas of his sick wife and two children and took Wilkinson away as a prisoner. He was soon dispatched with one of the swords.
At the third home they visited, Brown's band killed William Sherman with their swords and threw his body into a creek. Other men and a woman found at Sherman's home were not harmed. Through it all, Brown had decided, god-like, who would die and who would be spared, though according to his followers he did not actively participate in the executions. Whenever he was questioned about the events of that night, he was evasive.
The events at Lawrence and Pottawatomie caused the territory to erupt in guerrilla warfare, giving it the name "Bleeding Kansas." Brown's name became known to the nation, a Christian warrior to many who opposed slavery and a demented murderer to many other people.
On the night of October 16, 1859, Brown led 21 followers—five black men and 16 white ones, including two of Brown's sons—on a raid to seize the U.S. Arsenal at Harpers Ferry, Virginia (now West Virginia), where the Shenandoah River joins the North Branch of the Potomac. More than one version exists of what his plans were for the weapons he hoped to make off with. Some say he intended to create a state of free blacks in the mountains of western Virginia and Maryland. Others say he hoped to create an army of former slaves and freemen to march through Dixie, forcing slave owners to free their slaves. Brown himself may not have been entirely clear on what the next step would be, but he had convinced a number of Northern abolitionists to provide financial support for his actions, here and elsewhere.
Brown's raiders captured a number of prisoners, including George Washington's great-grand-nephew, Lewis Washington. Local militia trapped Brown and his men inside the arsenal's firehouse. During the short siege, three citizens of Harpers Ferry, including Mayor Fontaine Beckham. were killed. The first person to die in John Brown's raid, however, had been, ironically, a black railroad baggage handler named Hayward Shepherd, who confronted the raiders on the night they attacked the town. On October 18, a company of U.S. Marines, under the command of Army lieutenant colonel Robert E. Lee, broke into the building. Ten raiders were killed outright and seven others, including a wounded Brown, were captured.
Read more about John Brown's Raid On Harpers Ferry
He was tried and convicted for murder, conspiracy to incite a slave uprising, and treason against the Commonwealth of Virginia. He was hanged at Charles Town, the county seat near Harpers Ferry, on December 2. Among those watching the execution, "with unlimited, undeniable contempt" for Brown, was the future assassin of President Abraham Lincoln, John Wilkes Booth.
Brown had denied any plan "to excite or incite the slaves to rebellion or to make insurrection." He never intended to commit murder or treason or to destroy property, he claimed—though earlier that year he had purchased several hundred pikes and some firearms.
"Now if it is deemed necessary that I should forfeit my life for the furtherance of the ends of justice, and mingle my blood further with the blood of my children and with the blood of millions in this slave country whose rights are disregarded by wicked, cruel, and unjust enactments, I say let it be done," he said.
The "unjust enactments" included the Constitution, the Missouri Compromise of 1820, the Kansas-Nebraska Act, and the Supreme Court's ruling in the Dred Scott decision of 1857.
Initial reports of the raid on Harpers Ferry in Southern newspapers tended to view it as an isolated incident, the work of a mad fanatic and his followers. But when information began to surface that Brown had discussed his plans—to what extent is not known—with Northern abolitionists and had received moral and financial assistance, Southern attitudes turned sour. Many in the abolition movement painted Brown as a martyr, convincing many Southerners that abolitionists wished to commit genocide on white slave owners. Among abolitionists, Brown served as an inspiration to strive ever harder to abolish "the peculiar institution."
North and South drew even farther apart from each other. John Brown and his Harpers Ferry raid are often referred to as the match that lit the fuse on the powder keg of secession and civil war. Even today, debate continues on how Brown should be remembered: as a martyr to freedom, as a well-intended but misguided individual, or as a terrorist who hoped for revolution and, perhaps, murder on a grand scale.