By Eleanor Martinez-Proctor
Research Fellow, Historic New England
This post is a follow-up to research done on David Chesnut in 2022. See post, “Researching Black Histories from the Eustis Estate: Notes on Process.”
In 1903, David Chesnut Jr. was several years into his position at the Eustis Estate in Milton, working as a coachman alongside his brother Samuel, a groom. Their parents David Sr. and Elizabeth had come north from enslavement in the Carolinas and settled in Massachusetts. The young couple soon made their home in Milton where David Sr found employment as a “hostler,” or horse handler at the Eustis Estate. When the elder David passed away suddenly in 1898, his sons continued working for the Eustis family and the younger David oversaw their transition from carriages to automobiles, becoming the family’s first chauffeur.
At home, David Jr took on the role of principal provider for his remaining family. He would eventually move to Dedham and spend the remainder of his career as a chauffeur for the Endicott family at their large estate there. He was able to purchase land nearby on which he built and purchased several properties, investing in the local Black community not only as a landlord but as a community leader, veteran, air raid warden, lamplighter, military band director and patriarch of the Chesnut family. An accomplished trumpeter, his lifelong passion for music blossomed in successive generations as he raised musical sons who become performers deeply engaged in Boston’s “golden” jazz era, performing and teaching alongside legendary musicians such as Duke Ellington and Quincy Jones.
When David’s granddaughter Maria Chesnut Corman collaborated with Historic New England in 2023 on the exhibition, “Music and Motion: The Chesnut Family Legacy,” she generously shared a variety of treasured family objects and artifacts, including several books from David’s home in Dedham where she and her family lived with him for several years in the 1960’s. She noted that three books had particular significance to David and were always shelved together in the family’s living room. Those three books were the family Bible, a copy of Mary Boykin Chesnut’s “Diary from Dixie” and Booker T. Washington’s most famous work, “Up From Slavery,” which was inscribed in the front as a gift to David Jr. from W.E.C. Eustis’s sister Emily Jeffries. The importance of the Bible in the family’s religious life was clear; the other two books had specific and interesting connections to the family’s history.
Booker T. Washington was at the center of American consciousness in 1903 when the young David Jr. was working in Milton. Two years earlier, Washington had published “Up From Slavery,” the groundbreaking autobiography in which he detailed his journey being enslaved as a child, navigating race relations in the aftermath of the Civil War and the Reconstruction Era and eventually working to establish the Tuskeegee Institute. That July he came to Boston to speak at the African Methodist Episcopal Zion Church on Columbus Avenue. The reception was mixed, however, as one of his most vocal critics was in attendance: Harvard-educated William Monroe Trotter had founded Boston’s only Black newspaper, The Guardian, the same year “Up From Slavery” was published. The Guardian positioned itself at the forefront of Black radical progressivism; its motto was, “For Every Right, With All Thy Might.” Both Trotter and his close friend W.E.B. Dubois had deep ideological differences from Washington and The Guardian regularly criticized his views on segregation, his silence on lynching and the ways he positioned his message with white audiences.
During Washington’s remarks at the A.M.E. Zion church, Trotter and his associates (or “Trotterites,”) were reported to have interrupted the speaker with boos and hissing, leading to chaos in which the over 2,000 attendees were eventually dispersed by police in what quickly became known as “The Boston Riot.” Trotter and an associate were arrested and later convicted of disturbing the peace, although days later The Guardian’s headline shouted, “BOOKER WASHINGTON SPEAKS UNDER A CORDON OF POLICE – Tuskeegean Spends Two Hours Trying to Make Himself Heard – His Hirelings Protect Him from the Consequences of Facing His Own Previous Statements – Attempt to Deny Free Speech Foiled.”[1] By contrast, the Boston Sunday Journal noted that the disturbance was “in no way expressive of the feeling entertained toward Mr. Washington among the colored people of Boston and the vicinity. The disturbance was deliberately planned. It was participated in by only a few of those present.”[2]
Although David Chesnut Jr. could have been in the audience at the A.M.E. Church that day, his family remembers him as a quiet man who wasn’t known to attend large gatherings and pointedly steered clear of controversy. Either way, Booker T. Washington’s early life in Hales Ford, Virginia and the path he followed would likely have been of interest to David as it was to many Black Americans at the time. Although Washington’s ideologies clashed with figures like Trotter and DuBois, his ideas about productivity and economic independence resonated with Black Americans like David who looked to build lives and careers at the turn of the century. It is particularly interesting (and mysterious) that David was gifted an inscribed copy of this volume by Emily Jeffries, W.E.C. Eustis’ widowed sister who lived on the adjoining property to the Eustis Estate. It’s possible that the Chesnut family assisted with the horse and carriage needs of the Jeffries house which was in close proximity to them and, in effect, part of a family compound of sorts. Could this have been a commemorative gift, an acknowledgement that David had an interest in Washington’s work or an effort to introduce him to it? Whatever Emily’s reasoning, David kept the book in his possession for the remainder of his life and took particular care of it. Hardworking and practical, the choices David made reflect some of Washington’s philosophies and he is described by his family as having had a successful and fulfilling life. The fact that this book was kept alongside two other books of such significance quietly suggests that Washington’s work may have had a continuing influence on David.
“A Diary from Dixie” was an account of the years between 1861 and 1865 written by Mary Boykin Chesnut, the high-society wife of James Chesnut, Jr. Chesnut was a lawyer, senator, and general in the Confederate army who served as an aide to President Jefferson Davis. The Chesnuts were also large-scale enslavers who inherited a sizeable plantation called “Mulberry” in Camden, South Carolina and owned as many as one thousand enslaved persons who were emancipated at the end of the Civil War. “A Diary from Dixie” provides detailed descriptions of Charleston’s elite slaveholding class as the Confederacy fell and is seen as an important contribution to the historical record of that time. In addition, Mary’s personal observations about people and life on a large Southern plantation contain what may be the only references to specific figures at Mulberry, as enslavement records from this period can be notoriously hard to trace and were often not preserved. Mary’s book was first published in 1905, almost forty years after her death, and enjoyed wide popularity which may explain how it found its way to David Chesnut’s bookshelf. He could have been particularly interested in the work because of several apparent connections to his own history, the first of which is that his own father was born in 1853 in Camden, South Carolina, the location of Mulberry. The plantation was built around 1820 and the Black community there would have been enslaved by the prominent Chesnut family at the time David Sr’s birth. In addition, David Chesnut Sr spelled his last name without a “T” in the middle, the same way as James and Mary Chesnut which further suggests a connection to the family. Finally, David Chesnut Sr’s father is seen on several records as “James Chesnut.” It’s difficult to say whether this James Chesnut was an enslaved person named after their enslaver (which was a common practice) or if it refers to the fact that white slaveowners often included sexual assault in their abuse of power, fathering children with women whom they had enslaved. In both cases, the use of this name strongly suggests a deep connection to James and Mary Boykin Chesnut and provides an important clue to the family’s history.
[1] The Guardian, Aug.1, 1903
[2] Boston Sunday Journal, Aug.2, 1903.
