The Dudley Family & Their Enslaved People

Joseph Dudley, Brill the Enslaved Coachman, and Enslaved Indians

The enslaver Joseph Dudley
Listen to an AI-generated narration of “Joseph Dudley, Brill the Enslaved Coachman, and Enslaved Indians”.
UPDATED: Nov 2, 2022.


Rebecca Tyng Dudley died in 1722, two years after her husband, Governor Joseph Dudley, bequeathed (.pdf pg 402) to her his vaguely-defined and unquantified “servants”; Dudley noted neither the status–indentured, Negro, or Indian–nor number of servants. Fortunately, UW Madison historian Gloria McCahon Whiting notes in a 2020 journal article that Rebecca Dudley’s will specified that Brill, her “negro servant,” would be freed within a year of her death–that is unless her children required his services.

Through the miracle of digital collections, we can see an image of Rebecca’s original will above (see p. 2). In addition to Brill, the man Whiting leads us to, Rebecca further specifies, “I give Jimmy Negro to my eldest son.” Paul was Rebecca’s oldest son; he is the Dudley that conspired with his father to traffic an enslaved boy from a pirate ship. I’m still searching for more details about Jimmy, but as luck would have it, the Massachusetts Historical Society’s Collections contain two credible witnesses to Brill’s life in bondage: Judge Samuel Sewall and Judge Waitstill Winthrop.

The first record I came across is when prolific diarist Samuel Sewall noted at least 2 encounters with Brill in 1713.  On February 16th, “Brill calls just at night, From the Govr enquires of my Son’s Wellfare,” and on February 25th, “Brill Comes to Town, and acquaints that the Govr was taken with a sore Fit of Gravel last night so can’t be at Council today.” (Sewell pp 371, 372). 

Joseph Dudley served as governor from 1705-1715, so we apparently have the same servant Brill in Rebecca Dudley’s 1722 will relaying messages to Samuel Sewall nine years earlier. In later diary entries, Sewall paints the picture of Brill as Governor Dudley’s coachman. On July 5, 1714, Sewall notes a time when the governor’s chariot failed at B. White’s and that “Brill could fetch the coach.”

In October 1719, Sewall records that his granddaughter Hannah Sewall, who is also the granddaughter of Governor Dudley, dies and Brill is the one to transport her body: “I go to Brooklin[e] in my Son’s Calash. I see my daughter and all the Gov’s family are for burying at Boston: Two Sons and a daughter are buried there already. I consented. By my persuasion Brill brings the Corps to Town in Gov Dudley’s Chariot.”

Excerpt from The Diary of Samuel Sewall, April 1719
Excerpt from The Diary of Samuel Sewall, April 1719

Brill seems to be well-known in the town of Roxbury; he not only appears in Samuel Sewall’s diaries but is attested to earlier in 1711 letters from Waitstill Winthrop to his son John (husband to Ann Dudley and son-in-law to Governor Joseph Dudley).  Waitstill, writing from Connecticut, dispatches a series of letters to dissuade John and his family from visiting from Boston. In a July 24th letter, Winthrop warns, “If Brill drives the coach, he must see that the wheels and axeltre be well greased, least it heat and burn off. You must be sure that every thing be sound, and that the coachman be not in drink.” Winthrop confirms that this is our man Brill when Winthrop writes two days later by asking, “I know not how you will all com in the Governor’s coach and if a wheele or axltre brake in the woods, how will the children get to any shelter?”

Excerpt from Collections of the Massachusetts Historical Society. (1892)

The last entry I’ve found mentioning Brill before Rebecca Dudley’s will is Judge Sewall noting that on March 30, 1720, Governor Dudley is on his deathbed and “Brill came to Town in the Morning; Put up a Note at [Rev. Benjamin] Colman’s [house].” Joseph Dudley died three days later.   

I can’t find any narrative of Brill’s life using Google, Google Books, or Google Scholar. It’s safe to say that Joseph and Rebecca Dudley enslaving a Black coachman for 11 years is not a well-discussed fact and it’s exciting to share this with readers of this site. 

Enslaving Indigenous People

Of further interest to the slaveholding Dudleys was keeping native people in bondage. In the ”Roxbury Deaths” section of the Vital Records of Roxbury, Massachusetts to the end of the year 1849, under the heading “INDIANS”, we find listed “Peter…servant to Joseph Dudley, Esq.” dying in 1687, and “a girl of Mr Dudly, neer well of a pox, fell a bleeding and bled to death” dying in 1679. Joseph Dudley, noted participant in the 1675-1678 King Philip’s War, seemed to have kept some of the war’s human bounty for himself.  

Indian deaths as recorded on pg 680 of Vital Records of Roxbury. “Dudly” is a common misspelling and Joseph is the only other adult male Dudley living in Roxbury in 1679. His two surviving brothers lived in Boston (near present-day Faneuil Hall) and Exeter, NH respectively.

To understand further how widespread the practice of enslaving the indigenous people of New England was, look at this informative item from Brown University: Colonial enslavement of Native Americans included those who surrendered, too.

While natives had been forced into slavery and servitude as early as 1636, it was not until King Philip’s War that natives were enslaved in large numbers, Fisher wrote in the study. The 1675 to 1676 war pitted Native American leader King Philip, also known as Metacom, and his allies against the English colonial settlers.

During the war, New England colonies routinely shipped Native Americans as slaves to Barbados, Bermuda, Jamaica, the Azores, Spain and Tangier in North Africa, Fisher said.

– Brown University

Not surprisingly, the enthusiasm for enslaving Native Americans and enslaving people to be chauffeurs was a Dudley family trait. In the Letter-Book of Samuel Sewall, also from the Massachusetts Historical Society’s Collections, we find Sewall writing a 1713 letter to Reverend Treat of Eastham, Massachusetts on behalf of Governor Dudley’s sister who “stands in great need of a Servant; and would fain have an Indian youth of 10 to 12 years of Age, to live in Service till he be 21 years old…They keep a Calash, and want a Lad to drive it, and look after the Horse.”

Excerpt from Letter-Book of Samuel Sewall (Aug 10, 1713)

It’s almost irrelevant if this request for the human trafficking of a child went fulfilled or not; this letter further illustrates how slavery–of both African and Indigenous people–was not only casual and mundane to the Dudley family, they embraced it.


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Copyright Wayne Tucker 2023. This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License