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Frederick Douglass was many things: a gifted writer, a brilliant orator, a shrewd political strategist. But he was most certainly not a pacifist. He welcomed the Civil War as the best means to end slavery and helped two of his sons enlist in the Union army. Douglass was also a longtime confidant and admirer of John Brown, and well after the lethal Harpers Ferry Raid in October 1859, Douglass continued to pay tribute to the man that he (along with other devotees) called Captain Brown. None of this is in dispute. Yet what’s largely forgotten — and considerably more controversial — is Douglass’s murky role in the Harpers Ferry assault. A key member of Brown’s army allegedly told authorities that Douglass had broken his promise to join the insurrection. And well into the twentieth century, several of Brown’s immediate descendants, along with a friend from Boston who visited him as he faced execution, echoed this claim. The prevailing historical interpretation is that Douglass rejected Brown’s plan as a suicide mission. That view, however, is based almost entirely on Douglass’s own accounts of the uprising.

In late October 1859, two weeks after the assault on Harpers Ferry sparked a nationwide frenzy (and a manhunt for him), Douglass wrote a widely reprinted letter to the Rochester Democrat denying his involvement. Two decades later, in his third autobiography, Life and Times of Frederick Douglass, the author fully spelled out his case — and provided the basis for most subsequent accounts of his connection (or lack thereof) to the Harpers Ferry raid. The pivotal moment came in late August 1859, when Douglass met Brown in a quarry near Chambersburg, Pennsylvania (sixty miles north of Harpers Ferry, then in Virginia). According to Douglass, his radical friend called for “the taking of Harpers Ferry, of which Captain Brown had merely hinted before.” Douglass says he balked at the change of plans, because he viewed the arsenal town as a “steel-trap.” He claims to have instead favored an earlier blueprint that called for establishing a network of small encampments in the Alleghenies and encouraging slaves from the surrounding areas to flee. But there’s reason to question Douglass’s account. En route to the weekend summit in Chambersburg, Douglass had spent a night in Brooklyn at the home of two of the city’s leading black abolitionists, Reverend James Gloucester and his wife Elizabeth, a very successful businesswoman. Of Brown’s black correspondents, historian Benjamin Quarles later wrote, “none spoke in more militant tones than James Gloucester.” After Douglass’s stay, Elizabeth Gloucester gave him a short letter to deliver to Brown. Her note highlighted the famous abolitionist’s excitement about Brown’s work. “The visit of our mutual friend Douglass,” she said, “has somewhat revived my rather drooping spirits in the cause, but seeing such ambition & enterprise in him I am again encouraged.” She enclosed ten dollars in the letter, which Douglass passed along to Brown a few days later. Whether the Gloucesters would have shown such enthusiasm for the plan Douglass claimed to support is not clear. In a March 1858 letter, penned after Brown’s recent week-long stay at his home in Downtown Brooklyn, Rev. Gloucester told his houseguest that “in the language of that noble patriot of his country (Patrick Henry) [we shall] now use the means that God and nature ha[ve] placed within our power.” He then pledged twenty-five dollars in support of Brown’s developing plans, which Douglass subsequently delivered. When Elizabeth died in 1883, James told the Brooklyn Daily Eagle that en route to Harpers Ferry, Brown had remarked to her, “I wish you were a man, for I’d like to have you invade the South with my little band.” Douglass mentions his stay in Brooklyn in his own account, citing it as a key reason why he wouldn’t have been able to defeat the criminal charges he faced in Virginia. “They could prove I brought money” to Brown, he writes — making made him an accomplice to an act of treason.

In the aftermath of the Harpers Ferry uprising, John E. Cook, Brown’s advance man for the raid, ratted out Douglass, reportedly telling authorities that Douglass did not carry out his end of the mission. According to the Richmond Daily Dispatch, Cook informed his captors that Douglass was supposed to arrive with a “large band” of fellow raiders at a schoolhouse near Harpers Ferry, which Cook had seized on the Monday morning after the Sunday night assault. “I conveyed the arms there for him and waited until nearly night, but the coward did not come,” Cook was quoted as saying. That detail didn’t make it into Cook’s lengthy confession, read before the court. But Cook did state that Douglass was fully aware of the planned raid. The teacher whose school was seized also told the court that Cook had spoken of Douglass’s involvement in plotting the attack, which was supposed to have grown exponentially larger that Monday. (He didn’t specifically state that Douglass was slated to show up, however.) As Brown awaited the gallows, two of his longtime white abolitionist allies from Boston, Judge Thomas and Nellie Russell, paid him a visit. A half-century later, Nellie told the New York Evening Post that the condemned figurehead had bemoaned the “great opportunity lost” at Harpers Ferry, and claimed, “That we owe to the famous Mr. Frederick Douglass.” And historian Louis A. DeCaro Jr reports that Brown’s family was similarly sour about Douglass’s actions. Beginning with his children Anne Brown Adams and John Brown Jr, and continuing for several subsequent generations, the martyred abolitionist’s family felt betrayed by Douglass.