Mary Ellen Pleasant, Black American entrepreneur and anti-slavery activist, was a key supporter of the Underground Railroad and one of Brown’s largest financial backers. Her first husband, James Smith, was a Black “a wealthy former plantation owner and an abolitionist” and passed as white [1], [2].

Pleasant and Smith worked together to help fugitives. After his death, he left instructions and funding for her to continue this work [3].

Eventually she settled in San Francisco with her second husband, John James Pleasant. John and Mary Ellen combined their efforts to continue to help fugitives and to “[help] them find employment.” While in California, Pleasant also opened several restaurants and was a partner in several other money-making ventures [4].

Between 1857-1859, Pleasant used her wealth to support Brown. She met Brown in Chatham, Canada, in 1858 and donated “$30,000 to his cause” [5].

In a 1904 interview with the People’s Press about her relationship with Brown, Pleasant discussed a puzzling letter found on Brown when he was captured at Harpers Ferry, which read, “The axe is laid at the root of the tree and after the first blow is struck there will be plenty more money coming. W.E.P” [6].

Pleasant explained that this note is related to her financial support for Brown:

“I furnished the money and wrote the letter. My initials are M.E.P. for Mary E. Pleasant, but in signing my name I have always made the M so that it looks like a W, and I suppose that little mistake was all that saved me from being captured and hanging alongside of John Brown, and sometimes I wished that I had gone up on the scaffold with him, for I would at least have died in a good cause and in good company” [7].

Pleasant had been very careful to hide her involvement with Brown, discussing it with no one. Besides funding Brown, Pleasant also rallied enslaved people to his cause. After she met with Brown for the last time in Chatham, Pleasant, disguised as a jockey, and a friend “began meeting with the enslaved at various plantations to help ‘incite an uprising of the slaves’” [8].

Her efforts were thwarted when Brown struck the blow earlier than planned, likely due to suspicions about the Kennedy Farm and his and his allies’ actions there: “The affair upon which I had staked my money and built so much hope was a fiasco” [9].

After the Raid was over and authorities began searching for anyone suspected of being involved, Pleasant took further precautions to avoid detection by using the pseudonym Ellen Smith. In doing so, she was able to safely get back to San Francisco [10].

After Brown was executed, Pleasant “received one more letter from Brown,” which she immediately destroyed [11].

Pleasant asserted that:

“Brown was an earnest, sincere man and as brave a man as ever lived…but he lacked judgement and was sometimes foolhardy and cranky. He wrote too much and talked too much” [12].

Pleasant so valued her friendship with Brown that she requested her tombstone be inscribed with the phrase “She was a friend of John Brown” [13].


Created by Jessica Thelen. This page is created thanks to the permission Dr. Kellie Carter Jackson granted me to visually represent her work in this way.


[1] Jackson, Kellie Carter. Force And Freedom: Black Abolitionists and the Politics of Violence. University of Pennsylvania Press, 2020, p. 113. 

[2] Lowe, T. “Mary Ellen Pleasant (1814-1904).” Black Past, 

[3] Lowe “Mary Ellen Pleasant (1814-1904).”

[4]. Jackson 113. 

[5] $30,000 in 1858 is worth $934,931.71 in 2019. See Jackson 113.

[6] Jackson 113.

[7] Jackson 115.

[8] Jackson 115.

[9] Jackson 115.

[10] Jackson 116.

[11] Jackson 117. 

[12] Jackson 117. 

[13] Jackson 117.