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A Madman's Will: John Randolph, Four Hundred Slaves, and the Mirage of Freedom

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The untold saga of John Randolph’s 383 slaves, freed in his much-contested will of 1821, finally comes to light. Few legal cases in American history are as riveting as the controversy surrounding the will of Virginia Senator John Randolph (1773–1833), which―almost inexplicably―freed all 383 of his slaves in one of the largest and most publicized manumissions in American history. So famous is the case that Ta-Nehisi Coates has used it to condemn Randolph’s cousin, Thomas Jefferson, for failing to free his own slaves. With this groundbreaking investigation, historian Gregory May now reveals a more surprising story, showing how madness and scandal shaped John Randolph’s wildly shifting attitudes toward his slaves―and how endemic prejudice in the North ultimately deprived the freedmen of the land Randolph had promised them. Sweeping from the legal spectacle of the contested will through the freedmen’s dramatic flight and horrific reception in Ohio, A Madman’s Will is an extraordinary saga about the alluring promise of freedom and its tragic limitations. 20 black-and-white illustrations throughout

416 pages, Hardcover

First published April 11, 2023

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Gregory May

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5 stars
43 (22%)
4 stars
68 (35%)
3 stars
67 (35%)
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12 (6%)
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Displaying 1 - 30 of 32 reviews
Profile Image for Brendan (History Nerds United).
802 reviews703 followers
February 24, 2023
John Randolph was a madman alright. He owned 383 slaves. He defended the institution of slavery. Well, mostly. He manumitted all 383 slaves when he died. Or did he? When you have multiple wills, with multiple codicils, and a penchant for changing your mind on a whim while making people angry, it can be hard to tell.

Gregory May looks into the life, but also the death of John Randolph in A Madman's Will. The book feels like a historical offshoot of a true crime tome. I learned a little bit about John Randolph but a lot about manumission, how wills could be ridiculously easy to contest, and how people's belief in slavery was a much bigger sliding scale than I realized. Some people were the regular horrible racists we know and hope lose in the end. Some were against slavery but had slaves. Some just flip flopped to a maddening degree.

In the end, Randolph's will mattered because the lives of 383 people depended upon it. However, the book shows that freedom doesn't mean acceptance.

(This book was provided as an advance copy by Netgalley and W.W. Norton & Company.)
Profile Image for Dawn Michelle.
3,084 reviews
July 24, 2023
I wanted to love this book. I wanted to learn more about this time frame [I only knew snatches of this bit of history]. I waited a long time to read/listen to this and when the audiobook finally became available to me [and as soon as I could squeeze it in], I was all in. Unfortunately, it was not all I hoped it to be.

This book is a real slog at times. There is little about John Randolph and a whole lot about wills and manumission and other things that I didn't understand [and plenty that I did; its not hard to see racism when it is right in front of you and there is a TON of that in history and this book covers a good chunk of it]. There is greed and selfishness and plain meanness. And a lot of the same information over and over [which is where it really slogs].

There were really good parts though - I had no idea that Ohio was as *AHEM* quite as against "free slaves" as they turned out to be and learning about that part of history was very enlightening. And learning that being free doesn't actually mean acceptance was again very eye opening [imagine being set free; 13 years pass before it truly happens, and you are then told to get out of the very state you have lived your whole life and then you must W A L K 500 miles {plus travel by boat} to a city that doesn't want you and makes no bones about it] to me and again, I spent much of this book either being totally pissed off or crying my eyes out.

I wish the book as a whole would have been more cohesive and better planned out - there was a lot in there that a common layperson is just not going to understand and that could have been written in a different way so those of us not steeped in historical law could understand, or IMO, left out. Even with the parts that were really good, it was still rather a disappointment for me overall.

I waited a long time for this audiobook and was so glad when my request was granted for a copy and I am glad that I was able to listen to this book rather than try and read read it.
Unfortunately, I think that the narration added to some of my confusion and not loving this book. The narrator has a great voice and really great enunciation and pronunciation, but he reads SO FLIPPING FAST that I ended up losing a lot of the book because of that. If you can listen to really quick narration, then this guy is for you [it is the ONLY negative I have for him and would listen to him again if not for that one issue].

Thank you to NetGalley, Gregory May, Johnny Heller - Narrator, W. W. Norton & Company, and Dreamscape Media for providing the eARC and audiobook ARC in exchange for an honest review.
Profile Image for Janalyn, the blind reviewer.
4,616 reviews140 followers
July 11, 2023
In 1821 John Randolph a Virginia senator and a man of great wealth put and his will that all his slaves would be freed and given $10,000 to relocate. It would take 13 years and 30 of the slaves wouldn’t make it to see freedom but six unborn babies and countless other infants and toddlers would only know freedom thanks to the will and people hell-bent on doing the right thing. His cousins the Tuckers, protested the will because in it Senator Randolph said dude to the thievery of their father and the things taken from him and his brothers when they were minors would pay justice to those acts if anyone should contest the will then they would be excluded from it if and when they lost the case. He had many other provisions and addendum‘s but they are too great to go into in this review just know if you love historical nonfiction this one is a doozy and a great read. There’s even a chapter about a man whose name was Gaul about how he had the gall to say generations to come with Skoff at the fact they wanted to free the slaves not in those words exactly I am paraphrasing but essentially that we today would look back and think ha ha how ridiculous they wanted to free people from bondage. Well I guess the joke is on him because I think it’s utterly ridiculous that he fought to keep them there. This is a great book and it’s just sad this was a part of our history to begin with. I thoroughly enjoyed this book and highly recommend it. I listen to the audiobook in Jonathan Heller narrated it and he now rates a lot of nonfiction books and always does a stellar job. I would I want to thank dreamscape media and Net Galley for my free arc copy please forgive any mistakes as I am blind and dictate my review.
Profile Image for gnarlyhiker.
371 reviews16 followers
June 2, 2023
while informative and in conclusion a worthwhile read, it was a big chore to read

good luck
Profile Image for Molly.
97 reviews
November 4, 2023
Dude, fuck white people and fuck America. Reparations for all Black Americans.
1,201 reviews3 followers
September 20, 2023
"A Madman's Will" deals with an interesting subject matter, but the book was quite a slog to get through.
Profile Image for Katrisa.
447 reviews14 followers
August 2, 2023
3.5 stars.
This book has a lot of information. Parts were a bit dry. The strength of this book was in the way that it showed how convoluted the issues of slavery/abolition were. There was much more going on than just being for or against slavery. Issues of racism muddied many of the abolitionist ideas when it came down to how to treat freed men and women. It was heartbreaking to see what happened once Randolph's will was enforced and his enslaved people finally set free.
291 reviews
August 8, 2023
John Randolph 'freeing' his slaves has been a toss-off note in any number of antebellum histories, usually portraying Randolph as a progressive, free thinker going against the mores of the times. May provides a scholarly but accessible deep dive into the reality of the situation, where Randolph's will was contested, languished in probate for years, and left the future of his to-be-freed slaves in limbo.
254 reviews
August 19, 2023
Interesting book. It gives yet another viewpoint of slavery in the United States, its contemporary consequences, and long-term effects that I had not considered. A worthwhile read.
Profile Image for ReadingForFun.
129 reviews1 follower
July 4, 2023
Interesting and informative — but incredibly granular.
Profile Image for Socraticgadfly.
1,412 reviews455 followers
July 12, 2024
Fascinating book, or more like 4-5 mini-books crammed together.

It's
1. A mini-bio of John Randolph, mainly Randolph's personal life, not his political life.
2. Related to that, a look at the number of different wills and codicils he had.
3. Related to both, his take on slavery and on states rights and how they were, to some degree, like Randolph the politico, a "tertium quid."
4. An overview of manumission in Virginia, especially with changes in state law there after the Nat Turner revolt. After the 1831 slave revolt, manumitting masters had to provide for their slaves’ short-term upkeep and they had to leave Virginia after a year.
5. The history of actually probating such a will, with such messiness, the issue of manumission, and Randolph's hatred for his Tucker half-siblings, some of which may have been irrational in a non-insanity sense, but none of which appears to be truly insane.
6. The difficulty of settling a few hundred slaves at one time in Ohio, and racism in the North at this time, especially with Ohio and other states of the "old Northwest" actually getting worse about this in the late 1830s and beyond.

OK, a bit more.

A true to life potboiler! I had heard of Randolph’s sister-in-law Nancy and the scandal over the abortion, miscarriage or whatever.

I did not realize that after his brother’s death, she became the housekeeper for, then wife of, Gouverneur Morris! And, yes, that would have pissed Randolph off.

Nor had I ever heard of this relationship with this Maria Ward. Nor the rumors that his affectionate regard for two of his older male house slaves was reportedly cover for relationships with them. This relates to Randolph's likely sterility, which was surely childhood related, unlike Washington and his young adulthood smallpox. (We don't know for sure what caused the likely sterility and other male developmental issues with Randolph.)

A big part of the book vis-a-vis the Tuckers is Randolph’s debt, the general debt of the Virginia planter class, and the issue of “entailed” slaves. (Think George Washington only owning abut half the slaves at Mount Vernon, because Martha brought the rest from her previous marriage and by law, George couldn’t touch them. Martha kept them enslaved, and unlike George, freed none at her death.)

Randolph eventually got himself out of debt, but slaves related to his mother’s remarriage, to St. George Tucker, along with the issue that slaves could be mortgaged (no, really, and discussed in detail by Edward Baptist) complicated his effort on this and added to his animus to his Tucker half-siblings. (Randolph had seen a lot of scions of the "First Families of Virginia" get into debt, wanted out of that trap, and lived frugally, eventually in an upscale log cabin, to do that. He saw specific instances of getting into debt from overspending, like distant kinsman Thomas Jefferson, and failure to adjust plantation ag practices. Randolph himself grew at least some wheat and corn, not just tobacco.)

So, when he died, some of them had incentive to contest his will and even try to have him found insane.

Playing a cameo role in that part, but for Randolph’s slave-freeing will? Francis Scott Key. The assistant bishop of the Episcopal Church of Virginia has a bigger role.

This book is somewhere between 4 and 5 stars. It is a bit convoluted. But, it doesn't deserve its low-star ratings.

It's convoluted because of Randolph's convoluted mind, the convolutions of Virginia and Ohio law and other things. And, per what I said about his sister-in-law's abortion, miscarriage or whatever? Re the full story behind that, John Randolph wasn't the biggest nutter in his own family.

Side note: We're also "there." No idea why this got a 1-star rating without review. Gotta love the 2-star reviewer who says she has "family in Virginia," but had never heard of Randolph, yet grabbed the book, and yet didn't like it.

Otherwise, the 4-star reviews are actually better than the 5-stars other than mine.

A good buck for real history buffs. If you're not one, then just don't pick it up in the first place.
607 reviews12 followers
October 4, 2023
3.5 rounded up. I wanted to read this book because I was interested in what happened to slaves after they were freed, especially the ones that were manumitted prior to the Civil War and to their descendants. Unfortunately that was the least part of the book. More of it was about Randolph and his death and the various wills and parts of wills he left scattered around and the processes of contesting them, which family members were contesting which will and why. There's lots of legalities. The writing is good enough to pull you through it, though lots of reviewers found it dry.

There is some (but not enough) about what was happening to these enslaved people for the thirteen years this process was playing out. They weren't still slaves because no one owned them, but they weren't exactly free either. But once they are actually freed, he seems to go by it pretty quickly. The book is not as long as you might think since at least a third of it is notes.

Incidentally in case you think John Randolph was some kind of humanitarian hero for freeing 400 slaves, the book makes it clear the reality was a lot more complicated. He did after all own 400 slaves and didn't free them in his life. He apparently suffered some pangs of conscience over slavery and slave owning. But he spent much of his life rationalizing and defending why it was OK and justifiable for him and the South generally to own slaves. Some of the versions of his will said nothing about freeing slaves.
955 reviews2 followers
July 29, 2023
*I received an audio review copy via NetGalley in exchange for an honest review.*

This is a fairly short book, with the audiobook clocking in at 8h 38m, but wow does it pack a lot of information into that amount of time. I think the strength of this book is in providing a real life example of how the antebellum United States wasn’t simply slavery vs abolition, and I think learning more about this period helps explain some of the issues of Reconstruction and even into modern times.

That being said I sometimes had a hard time following the narrative. Whether that was due to the writing style or the fact that I was solely listening to the story and not hybrid reading, I can’t be certain. That being said, I think Johnny Heller did an excellent job with the narration. However, I did feel like there were times the author started to focus on things that maybe weren’t as central to the story as others. It is also very clear that the author has trained as a lawyer because there were some parts related to Randolph’s will and the contestation of the will that for sure went over my head.
Profile Image for Carol Kearns.
190 reviews3 followers
September 8, 2023
A deep dive into all the legal convolutions of famous American John Randolph’s “last” will and testament. I listened to the book on Audible—the narrator is excellent and added to my understanding of the story. He is not a “slow reader” and kept the narrative moving at a good pace. I found the story of the Roanoke slaves to be very interesting (especially chapter 9); the infighting in John Randolph’s extended family didn’t hold as much interest for me. The book gave me new insights into the many severe disadvantages that freed slaves faced—poverty, lack of opportunity, prejudice based solely on their race, and horrible mistreatment in both the South and the North. I would recommend this if you want to learn more about slavery in the early 1800’s in Virginia. If you are interested in Ohio’s history with manumission during this time period you will also find it enlightening.
Profile Image for B..
2,577 reviews13 followers
April 30, 2023
I won a copy of this one in a goodreads giveaway. This one was a really slow read. See, it seemed a lot like this book wasn't quite sure what it wanted to focus on. Sometimes that focus was history. Sometimes that focus was on attempting to apply psychological analysis to historical figures based on historical documents. If it had just stuck with one or the other, my attention wouldn't have waned and waxed as hard as it did. While both branches of exploration are interesting, the back and forth both made it seem as though the book was absolutely dragging, and it made it very hard to stay engaged.
Author 1 book2 followers
December 8, 2025
The author presents some good historical detail. But unfortunately, he fills in what he doesn’t know with insufferable self-righteous supposition and political correctness. He is particularly remiss in not having read Time on the Cross, given his subject matter. He can’t bring himself to mention that ethnic chauvinism characterized all of history and all peoples before roughly WWII. Having invented the word "racist" ~1903, humanity's present particular virtue is relatively new. The author is a lawyer rather than a historian, but that is no excuse for the Presentism with which this book is rife.
315 reviews
July 3, 2024
I love history and have family in Virginia and never heard of this man or this case.
There was a lot of information and history presented however much of it was lost with the constant repetition and refrain of how much randolph hated his stepfather and half-sibling tucker relatives and how angry they were at him for accusing their father of impropriety AND how money hungry the wastrel tuckers were. This book could have used better editing for timeline and consistency.
Profile Image for Nav.
1,518 reviews1 follower
November 5, 2023
Somewhat more wide-ranging than you might expect (looks at why there were several wills, how they got challenged, the reputation of the dead man, why they were challenged, how judges were chosen, how being freed wasn't the end of the story and more) as it expands on a variety of factors you may not have considered on your own.
247 reviews2 followers
January 2, 2025
Audiobook. Senator John Randolph freed 383 slaves in his will in the largest manumission ever. He freed them with no thought of what came next. Of course the system was set up for them to fail, so freedom meant nothing. I definitely drifted in and out of listening to this one, as it was nonfiction.
This entire review has been hidden because of spoilers.
1,699 reviews20 followers
June 30, 2023
An interesting story that addresses many of the complexities and complications of the slave system in the South. The book wanders a bit into more general topics and loses its focus in places. The intricacies of the legal system are well addressed and developed.
Profile Image for Paul Downs.
487 reviews14 followers
August 24, 2023
Really, really well researched and written. Are you interested in how slave owners thought about it? This story is for you. Unfortunately, like all stories on this subject, there's no happy ending.
26 reviews
January 4, 2025
This book has everything: political fights, legal fights, family fights. Whether you are interested in the history of slavery, early American history, the development of legal precedents, legal reform, or family feuds, this book has it all.
2 reviews4 followers
July 12, 2023
Very interesting story. Narrator of the audio book was great and engaging. As a history buff it was nice to learn more about Ohio and some of its history with slavery and freeing the slaves.
59 reviews1 follower
August 23, 2023
Good. Thought about things I should have thought about before. I suspect that was the point. Worth reading, but not exciting.
Profile Image for Kim.
111 reviews
December 17, 2023
Fascinating how politics is always at the root of everything divisive and evil.
Profile Image for Daniel Coutz.
129 reviews
October 25, 2024
Fascinating story. Some of the chancery chapters were a little tedious but it was worth it to get to the chapters that take place in Ohio.
411 reviews1 follower
October 26, 2023
Excellent. Easy to read, follow, and comprehend. Well written with interesting photos and documentation. Very compelling and relatable story to USA's current events.
Displaying 1 - 30 of 32 reviews

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