Meet Monk Estill

Folklore makes ‘Uncle’ Monk Estill (d 1835) a compelling character. The whole Boonesborough milieu conveys a certain romanticism; it’s a tribute to Kentucky storytellers that Monk’s achievements have survived in the historic record. I have a debt of gratitude to record keepers. I salute individuals and organizations who’ve digitized records and nurtured searchable databases: their efforts inspired me to go into the Library of Congress, the National Archives and King Library at the University of Kentucky, to see whether I could do justice to Monk’s character, by piecing together and sifting apart the man’s story.

I discovered that Monk, slave-named Estill, saved my 4x, great-grandfather’s life in 1782. The informing intention of this blog was to reach out and hopefully build relationships with his living descendants. Given my work, to eliminate racial profiling and contribute to leadership development among those who’ve historically been on the downside of power – and the discovery of Monk’s profound contribution to my very being – I think myself fortunate in that I can elevate Monk’s story to public awareness.

Monk became the first slave freed in what is now known as Kentucky. I am highly motivated to discover the freedom papers issued by the heirs of militia captain James Estill (1750-1782), Monk’s slave master. Monk’s character is revealed by two, predominant assertions as to why he was freed. I take it his manumission was for valor. In one of the closing battles of the American Revolution (then called the Battle of Small – or Little – Mountain, now styled Estill’s Defeat), where British-supplied Wyandot warriors attacked Estill’s Station near Boonesborough and were then counter-attacked by a band of self-organized militia, my ancestor, private James Berry (c1752-1822) lay terribly wounded, having taken a musket ball to the thigh. The stout Monk carried Berry – on his back – at least 25 miles to safety. Berry subsequently began a family, which led to my occurrence.

Perhaps an indication of the dominant culture’s proclivity to diminish the character qualities of people of culture, less august historians circulate another rationale for Estill heirs to grant Monk his freedom: the black man’s chicanery.

Monk's ownership had changed, prior to the battle: he'd become booty, held of Native warriors. Caught beyond the stockade at Estill’s Station while male inhabitants pursued a Wyandot band, Monk does convince his captors not to attack the women and children left inside. He undoubtedly saved their lives as well.

It’s this branching interpretation of historical events which led to the scratchpad I call Hard Honesty. On so many matters, contemporary culture operates on assumptions drawn from a narrative that’s been falsified, massaged, or left incomplete. I often stumble upon false narratives that affirm the most damaging cultural conveyances upon race, and I assume you’ll want to know about it.

It’s what Monk did with his freedom that astounds me. Suddenly invested in his isolated, beleaguered wilderness community in a new way, he contributed to the group’s well-being. Monk unveiled his ability to produce gunpowder, a tremendously scare resource as revolutionaries back in civilization kept hold of their supplies to wage war with colonial power.

As I’ve grown closer to it, I understand Monk’s story to be not so much about what white folks did for him. His choices illuminate what an oppressed person can do for others.

Understanding the institution of slavery perhaps more intimately than the general population, I’m often astounded by the moral leadership that arises in civil rights workers who wend their way through ongoing legacy of racial injustice. I’ve found a theme. By extending our humanity to those who’ve been oppressed, the dominant culture is likely to reap unexpected rewards. Seeking the civil rights of others is actually an expression of self-interest.

An examination of Monk Estill’s life is an opportunity to reflect on valor. An understanding of how aspiring men at Boonesborough collaboratively pursued liberty puts a dent in America’s precepts about ‘self-reliance.’ These forays into the historical record are designed to interfere with your assumptions about history. I’ll honor Monk’s memory by sharing how race has colored our thinking … to the detriment of oppressors as well as the oppressed.

Anyone with information regarding the extraordinary Monk Estill is requested to leave a message at (503) 395-0001.

Roger David Hardesty
Portland, Oregon


  1. I found your blog while searching for a picture of Monk. My ancestor was John Harper, who led the men to bury the bodies after Estill's defeat. Thank you for the interesting post, I'd like to include a link to it from my blog.

  2. My name is Christian Ballew and I am a descendant of Monk Estill. I live in Cincinnati Ohio feel free to reach out to me


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