Book Review: A Madman’s Will: John Randolph, 400 Slaves, and the Mirage of Freedom

A Madman’s Will: John Randolph, 400 Slaves, and the Mirage of Freedom. By Gregory May. New York: Liveright Publishing Corporation, 2023. Hardcover, 416 pp. $30.00.

Reviewed by James “Trae” Welborn

Historian Gregory May aptly describes the focus of this excellent work as “a book about the lives of many individual people–famous and unknown, free and enslaved, self-righteous and much wronged–who experienced the difficult contradictions in antebellum American life in ways quite different than we usually imagine. At the center of the book is a sharply contested will that freed more slaves than almost any other will in American history.” (xxiii) With this focus clearly established, however, May poignantly asserts that the book explores far more than the legal battle over this particular will and the manumission it sought to enact.

Through this complex and contentious process May plumbs the complex depths of race and slavery in the antebellum United States, revealing the deep-seated racism that pervaded racial ideology and social convention among white Americans that complicate the often neatly conceived lines between “free North” and “slave South” during the era and counter prevailing tendencies to analyze the history of slavery “in terms of Black self-assertion and white guilt.” “While that formulation is revealing,” May astutely argues that “it has diverted attention from a more troubling historical truth that continues to have devastating consequences. That truth is white incomprehension and indifference. . . . Inertia is not as uplifting a theme as Black agency but it has been a more powerful historical force.” (xxii) The result is an impressively researched and nuanced portrait of both white slaveholding and Black experiences of enslavement, manumission, and a persistently contested and inherently limited freedom under the twin shadows of the slave system and the broader prejudicial assumptions and discriminatory practices of white supremacy that extended well beyond both the geographic borders of the Slave South’s regime and the chronological parameters of the Civil War Era.

In the five chapters that comprise “Part One,” May details the most pertinent aspects of John Randolph’s life and career as related to his last will enacting manumission of nearly 400 of those enslaved on his estate. May begins with the circumstances surrounding Randolph’s 1832 death in Philadelphia, Pennsylvania, and his deathbed declaration that he intended to free his enslaved property in his last will and testament, a declaration that ushered in a decade of contentious legal battles surrounding the execution of Randolph’s last wishes by exposing the convoluted nature of his intentions toward his enslaved property as recorded in multiple iterations of his last will and testament over the course of his life. Persistent rumors surrounding Randolph’s intent to manumit his enslaved property combined with consistent speculation regarding his sanity and a complex web of familial and legal relations (namely lifelong friend and primary legal counsel Judge William Leigh as well as extensive kinship ties to the Tucker family, beginning with his stepfather St. George Tucker) to envelop Randolph and his estate in controversy throughout his life and in death.

John Randolph’s vacillating perspectives on slavery and manumission in life further complicated the contest over his last will and testament upon his death and fundamentally shaped associated assertions of his “sanity” or “madness” by interested parties, both of which only exacerbated tensions between various family members and legal entities tasked with trying or hearing the multiple cases that this contested will eventually produced. These complex dynamics are the focus of May’s analysis in the five chapters of “Part Two.” Here May deftly maneuvers between analysis of the complicated legal precedents and structures governing the slave system and the equally complicated family dynamics among the Randolph and Tucker heirs, all of which became a very public spectacle that was national in scope. Randolph’s notoriety in life shaped the posthumous contest over his will, and that legal contest assumed projected meaning from every quarter amidst the intensifying sectional crisis over slavery. From the most ardent proslavery southerners to the most “radical” northern abolitionists to the middle majority of whites on both sides of the sectional divide who shared much the same racial prejudice alongside nominally similar reservations about slavery, even as they expressed these views in increasingly divergent and antagonistic sectional terms, May’s analysis expertly situates the decade-long legal battle over the will into this broader sectional context.

Throughout May seizes every opportunity to center the perspectives and experiences of the enslaved “defendants” at the heart of the case, despite their explicit exclusion as formal defendants under the law and an overt neglect of their input by all white counselors and litigants, even those defending their claim to freedom.

This focus on the formerly enslaved following the legal confirmation of their manumission continues into “Part Three,” where May asserts that pronounced racial prejudice and often violent acts of discrimination by whites in Ohio, where restrictive Virginia statues led them to resettle, eventually eroded the nature of their freedom in ways that revealed the deep-seated place of white supremacy in U.S. society and culture during the period and presaged its perpetuity in the civil rights struggles of African Americans during Reconstruction, in resistance to the Jim Crow regime that followed, and in continued struggles for social justice of the more recent past and present.

May’s epilogue assertively concludes that previous analyses of Randoph’s act of manumission have typically missed the point, in whole or in part: “the character of slaveholders who did or did not free their slaves is not the issue anyway….History is a process propelled by many wills. Praise and condemnation shed little light on the jumble of human motives, and they explain almost nothing about the workings of the historical process. We must think beyond that to understand why those who chose to free their slaves made so little difference.” (278) Returning to a theme laid out in the preface, May reiterates that “before every person had a legal right to freedom, the gift of freedom was not liberating. Because manumission was just an exercise of the giver’s rights, it changed almost nothing. It did not challenge the law or the social order. It gave the recipient no more than the law and social mores were prepared to concede…. A man who released the workforce his family needed was more likely to be called mad than righteous.” (278) As May emphasizes from the outset, his analysis of Randolph’s will and the experiences of the formerly enslaved whom the law begrudgingly granted a very proscribed freedom constitute “not a parable about justice, but an enormously powerful encounter with the enduring pain and provocative ambiguity of our past. What it means for us today depends, as James Baldwin put it, on ‘what we make of the questions with which the story leaves us.’” (xxiii)

As an imminently accessible narrative history of an important and widely familiar, if often misunderstood, historical figure and moment, May’s work will appeal to both scholars and more general readers alike. For scholars, May situates his thorough archival research into the expansive legal documents and family papers of the Randolph and Tucker families into the broader historiography on race and slavery in the United States during the Civil War Era, most notably building upon recent scholarship by Samantha Seely (Race, Removal, and the Right to Remain), Kendra Taira Field, Growing Up with the Country), Jeff Forret (Williams’ Gang), W. Caleb McDaniel (Sweet Taste of Liberty), and Joshua D. Rothman (The Ledger and the Chain). In so doing May effectively merges legal and cultural historical methodologies to reveal the complex dynamics of contests over race and slavery in operation during the antebellum sectional crisis, but conveys these crucial insights and interpretive conclusions in an enviably accessible narrative prose sure to engage more general readers interested in the intersection of race and slavery in American history and the continued implications of these intersections in the present.

Dr. James “Trae” Welborn is Assistant Professor of History at Georgia College & State University in Milledgeville, Georgia. Born in Charleston, South Carolina, reared in Fernandina Beach, Florida, and educated at Clemson University and the University of Georgia, Dr. Welborn specializes in American cultural history, with an emphasis on the emotional dimensions of evolving conceptions of virtue, vice, and the role of violence in shaping these cultural values during the American Civil War Era. The University of Virginia Press published his book, Dueling Cultures, Damnable Legacies: Southern Violence and White Supremacy in the Civil War Era, in 2023.