Paul Dudley: Pirates, Grift, and a Baptism


The Dudley Family & Their Enslaved People

Paul Dudley: Pirates, Grift, and a Baptism

Listen to a computer-generated narration of “Paul Dudley: Pirates, Epic Grift, and a Baptism”.
UPDATED: Nov 2, 2022. Eagle-eyed scholar Aabid Allibhai wrote to me to point out that I had not read Rebecca Dudley’s 1722 will close enough. I read that the bequest of Jimmy Negro was assigned to “my oldest son, William.” In fact, “oldest son” and “William” are two different people. Justice Paul Dudley was Rebecca Tyng Dudley’s oldest son, and “William” is the start of a new clause. Previously, I had written that Jimmy was bequeathed to William Dudley. I no longer believe that to be true and have adjusted my work accordingly.

was the son of Gov. Joseph, brother of William, and Chief Justice of the Massachusetts colonial government. Digging into archival records we find two stunning examples of Judge Paul Dudley enslaving Black people 40 years apart.

c. 1900 cigar box

The Dudleys, Pirates, and Clandestine Slave Trade

Looking in a “Calendar of State Papers” from a London archive published in 1916, we find a receipt showing in 1705 a “Negro boy taken from the pirate John Quelch* and sold to Paul Dudley for 20 [pounds], the highest bid at William Skinner’s Tavern Boston Oct 6.” This record is enclosed in Dudley’s response to John Colman’s complaint to the Council of Trade and Plantations in London. Colman was part owner of the vessel Charles, a privateering ship granted license by Governor Joseph Dudley. The crew of the Charles mutinied and attacked ships from Portugal, a British ally, and, upon return, the pirates were tried and executed. 

Excerpt from Calendar of State Papers Colonial, America and West Indies (1705)

What happened to the rest of the ship’s booty I am not sure of, but John Colman is quite upset that the “negro boy” he viewed as his property was funneled by Governor Joseph Dudley to his son Paul and sold to him for the very cheap price of 20 [pounds]. 

Colman writes to London requesting “[a] bond for the 50 [pounds] Governor Dudley squeezed out of us was given to his son, for the Governor. The sale of the negro boy was clandestine, for there had not been due notice there of, etc, etc.”  Dudley is dismissive, characterizing Colman’s complaint as a “foolish and groundless aspersion,” further responding “[t]he sale was public and there was another negro sold at the same time at the same price…The Judge never asked 5 p.c. for the condemnations of that prize…as Receiver [Colman was commissioned as Receiver General of Massachusetts] he has, for the most part, himself bought the prizes that have been imported to this place…”

John Colman appeals for additional compensation from Paul Dudley. From Calendar of State Papers

We don’t know if this “negro boy”–whose age is unknown–was originally enslaved by the British sailors or if he arrived in Boston “as plunder from piratical raids,” as Wesley Fiorentino puts it in the highly-recommended article about Quelch linked above. But we do know that Paul Dudley purchased an enslaved African from this ship and it’s likely his father the governor facilitated this, perhaps in a clandestine, extra-legal manner. 

But the dubiousness doesn’t stop there. The Massachusetts Attorney General at that time argued for an immediate admiralty trial, the first of its kind outside of England. The Attorney General, as it turns out, was also the prosecutor who won a conviction at the trial. His name? One Paul Dudley.

If that weren’t eyebrow-raising enough, legal scholar Stephen M. Sheppard notes:

Joseph Dudley appointed Paul to a three-man commission for seizing pirates and their treasure, along with future allies Nathaniel Byfield and Samuel Sewall. The commission took to its task with bravado, in some cases directing the attack force that rounded up the pirate bands. As attorney general, Dudley acted also as prosecutor and attracted quite a reputation from these trials, the most notorious of which was of Captain John Quelch, a strayed privateer. On the other hand, there was also the complaint that the trials (with the inevitable hangings to follow) were nothing more than judicial murder.

Stephen M. Sheppard, Paul Dudley: Heritage, Observation, and Conscience (2000. p. 8) St. Mary’s University School of Law

Pure shadiness. What could possibly go wrong when the official deciding who to prosecute for piracy is also on the commission in charge of seizing and divvying the ill-gotten “prizes” and, by the way, he is the governor’s son? This could be another hilarious iteration of entrenched Boston political corruption if there weren’t commodified humans on the auction block.

How many enslaved Africans did the Dudleys traffic through this pirate commission for their own—and other Dudley family members—gain? How many of them were children? And what could we learn about these enslaved people from the records? These are burning questions.

Guinea’s Baptism

Forty years later we have another record of a Black person enslaved by Paul Dudley. In the History of the First Church in Roxbury, Massachusetts, 1630-1904 under the heading “Church members admitted in brick school house“ – the brick school house was where the Roxbury congregation worshiped after the third meeting house burned—we find an entry “May 1745, Guinea, negro servant, maid to Judge Dudley.” Guinea’s baptism is recorded on the previous page and she is one of several examples of enslaved Africans being baptized church members in colonial Massachusetts. One of the first enslaved Africans to gain church membership was Dorcas the Blackmore, who joined the Dorchester church of her enslaver, Israel Stoughton. It’s worth noting that membership did not mean that an enslaved person was released from slavery.

List of new church members at Roxbury, including Guinea, an enslaved maid of Paul Dudley

(*As was noted in the entry on Joseph Dudley, Paul inherited Jimmy Negro from his mother Rebecca in 1722.)



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Nicholas Dudley, (different) Joseph Dudley, & Simon Bradstreet


The Dudley Family & Their Enslaved People

Nicholas Dudley, (different) Joseph Dudley, & Simon Bradstreet

Jospeh Dudley (Son of William)

This Joseph was a Boston lawyer and the son of William Dudley and nephew of Judge Paul Dudley, who was his guardian. In Joseph’s 1767 will he leaves “my negro-man named Cato” to his wife Abigail. (History of the Dudley Family .pdf pg 633)

Abstract of (other) Joseph Dudley’s 1767 will as printed in Dean Dudley’s History

Nicholas Dudley & Simon Bradstreet

Two other Dudley family members, Nicholas Dudley and Simon Bradstreet, may seem extrinsic to a discussion of the Dudleys’ relationship to Roxbury, but Simon Bradstreet was a colonial governor and the records of these two enslavers reveal names of enslaved people, a gift.

Nicholas was the great-grandson of Thomas Dudley through the Reverend Samuel Dudley (born in England before the migration and settled in Exeter, New Hampshire) and Stephen Dudley.

Dean Dudley recounts in History that in 1753 Nicholas “gave a receipt to his son-in-law Josiah Robinson…for five pounds in full for a female ‘Negro Slave named Kate’ then aged about eight.” Dean then casually recounts, with no further exposition that, after Nicholas died in 1766, “[t]he slaves mentioned in his will and other papers were soon set free, as slavery was abolished in New Hampshire in 1781” (History .pdf pg 302). Here, Dean Dudley’s 19th-century indifference to the cruelty faced by Black people sits stark naked on the page. 

Excerpt from Dean Dudley’s History of the Dudley Family, 1884

Simon Bradstreet was Thomas Dudley’s assistant in service to the Earl of Lincoln and married Thomas’s daughter, the famous poet Anne (Dudley) Bradstreet, before the Bradstreets and Dudleys settled in Massachusetts. Anne preceded Simon in death by 25 years, therefore it’s difficult to know what her relationship to enslaved people was.  According to Gloria McCahon Whiting’s article, Simon, who died in 1697, filed a 1689 will that bequeaths an enslaved African woman Hannah and her daughter Billah to his new wife. The Bradstreet family continued to enslave African Americans in Essex County, evidenced by one Chance Bradstreet, who was born enslaved and died a free man in 1810.

The poet Anne Bradstreet. Not to be confused with her husband’s second wife, Ann Bradstreet.

(Updated 08/22/2021)


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About & Contact

About & Contact

The Eleven Names Project is an independent digital research project first published by Wayne Tucker on August 22, 2021. I am a South Shore native and having spent time in Boston and in Metro West, I’ve returned to the South Shore.

The mission of the Eleven Names Project is to create and increase the digital footprints of Black, indigenous, and multiracial people in Massachusetts during the time of slavery (c. 1638 – 1783). In addition to my website, my work has been featured in The Bay State Banner, is cited multiple times by Harvard & the Legacy of Slavery, and I created a slavery research guide for the Hanover Historical Society.

Support grassroots authentic history. Consider a contribution to the Eleven Names Project.

Twitter: @elevennames

Patriot Ledger subscribers, read the story here. (Paywall)



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Bibliography, Additional Media, & Resources


Roxbury (Eliot) Burying Ground, 1954


Brown University (2017). Colonial enslavement of Native Americans included those who surrendered, too.

De Costa, J.,  and Hall, Charles.  “A plan of the town and harbour of Boston.”  Map.  1775.  Norman B. Leventhal Map & Education Center

Dudley, Dean (1886). The History of the Dudley Family. Wakefield, Mass .pdf Library of Congress

Dudley, Joseph (1675).  Letter from Joseph Dudley to John Leverett. Native Northeast Portal

Fiorentino, Wesley (2021). Pirates in Boston: The Trial and Execution of John Quelch. The Beehive (Massachusetts Historical Society).

Hardesty, Jared. (2017). Creating an Unfree Hinterland: Merchant Capital, Bound Labor, and Market Production in Eighteenth-century Massachusetts. Early American Studies, 15(1), 37-63.

Headlam, C. (1916). Calendar of State Papers Colonial, America and West Indies, Volume 23-1706-1708.

Hanscom, E. Deering. (1917). The heart of the Puritan: selections from letters and journals. New York: The Macmillan company.

Lincoln, Rose (2011). Hidden Spaces: The tiny cemetery. The Harvard Gazette

Massachusetts Historical Society (1892). Collections. Boston: Massachusetts Historical Society.

McNally, Deborah (2011). Dorcas The Blackmore (ca. 1620-?).

Miller, Yawu (2017). Re-writing Boston’s history of slavery: Efforts underway to change historic names. The Bay State Banner

Nodjimbadem, Katie (2017). Newly Uncovered Documents Address the Mystery of One Slave’s Life. SMITHSONIANMAG.COM

Poetry Foundation. Anne Bradstreet 1612-1672

Sheppard, Stephen M. (2000). Paul Dudley: Heritage, Observation, and Conscience. St. Mary’s University School of Law

Suffolk County, MA: Probate File Papers. Online database. New England Historic Genealogical Society, 2017-2019. (From records supplied by the Massachusetts Supreme Judicial Court Archives. Digitized images provided by *subscription/library access required

Thwing, W. Eliot. (1908). History of the First Church in Roxbury, Massachusetts, 1630-1904. Boston: W. A. Butterfield.

Vital Records of Roxbury, Massachusetts, to the End of the Year 1849. (1925). United States: Essex institute.

Whiting, G. (2020). Race, Slavery, and the Problem of Numbers in Early New England: A View from Probate Court. The William and Mary Quarterly, 77 (3), 405-440.

Additional Media and Resources

NB: I repeat some items from the bibliography for the sake of organization.

Re-writing Boston’s history of slavery: Efforts underway to change historic names (2017) by Yawu Miller for The Bay State Banner. This is a concise overview of the controversy surrounding the renaming of old Dudley Square written before the name changed to Nubian Square.

Introductory talks about New England slavery

Jared Hardesty gives an authentic overview of the realities of slavery in New England
Wilberforce Institute, University of Hull (UK): This webinar introduces some of the major scholars who are contributing to this dynamic field – Jared Hardesty, Gloria McCahon Whiting and Margaret Newell – along with commentary from two very distinguished historians of New England and Canada – Mark Peterson and Charmaine Nelson. The speakers will reveal how important the question of slavery was in Massachusetts, despite the small number of the enslaved, and outline a range of historical opinion on slavery and emancipation in this fascinating British colony and American state.

Roxbury, Past and Present

About Roxbury Roxbury Historical Society

Two independent short films on contemporary Roxbury (2003, 2015) by Tessil Collins with ensuing discussion

Drake, F. S. (Francis Samuel). (1878). The town of Roxbury: its memorable persons and places, its history and antiquities, with numerous illustrations of its old landmarks and noted personages. Roxbury.

Glimpses of Early Roxbury: General Society of the Daughters of the Revolution. Massachusetts. Mary Warren Chapter, Roxbury (1905).Boston

Thwing, W. Eliot. (1908). History of the First Church in Roxbury, Massachusetts, 1630-1904. Boston: W. A. Butterfield.

Vital Records of Roxbury, Massachusetts, to the End of the Year 1849. (1925). United States: Essex institute.

Nubian Square mural by ProBlak, GoFive, Soems, and P. 14Teen Wright. 2019. Photo: September 2021.

Further Background on Boston Colonial Slavery

The Shirley-Eustis Place: Working Report On Slavery At The Shirley-Eustis House (2021) by Aabid Allibhai, JD. PhD Candidate, African & African American Studies Harvard University (Jump to .pdf pg 63)

Lifelong residents of Shirley Street (the overwhelming majority of Shirley Street residents) and the Dudley Street Neighborhood Initiative (DSNI) know the structure at 42-44 Shirley Street to be a former slave quarters in addition to a barn. They learned this from the folks at the Shirley-Eustis House in the 1980s. In fact, this information is part of the tours given by DSNI. This would make 42-44 Shirley Street one of only two still-standing slave quarters in the northern United States (the other being the slave quarters at the Royall House and Slave Quarters in Medford, MA). Shirley had white indentured servants and presumably live-in secretaries while governor of Massachusetts, perhaps forcing his slaves to live at 42-44 Shirley Street due to lack of living space in the main house. Eliakim Hutchinson, one of the richest men in Boston, owned many slaves, perhaps forcing some of them to live at 42-44 Shirley Street for the same reason.

– Aabid Allibhai

The Royall House and Slave Quarters of Medford, Massachusetts

In the eighteenth century, the Royall House and Slave Quarters was home to the largest slaveholding family in Massachusetts and the enslaved Africans who made their lavish way of life possible. Today, the Royall House and Slave Quarters is a museum whose architecture, household items, archaeological artifacts, and programs bear witness to intertwined stories of wealth and bondage, set against the backdrop of America’s quest for independence.

Boston Middle Passage Project – In October 2020, the Middle Passage and Port Marker Boston Partnership installed a permanent marker on Long Wharf. It acknowledges Boston as a port of entry for enslaved Africans.

Nodjimbadem, Katie (2017). Newly Uncovered Documents Address the Mystery of One Slave’s Life. SMITHSONIANMAG.COM

Paul Dudley’s “parting stone” in front of 3 Centre St in John Eliot Square. Part of a network of mile marker stones erected of Paul Dudley’s lifetime, this stone marks the divergence of the roads to Dedham and Rhode Island on the left, and to Cambridge on the right. September 2021.

Books with Complimentary Podcasts

New England Bound: Slavery and Colonization in Early America (2016) by Wendy Warren

While earlier histories of slavery largely confine themselves to the South, Warren’s “panoptical exploration” (Christian Science Monitor) links the growth of the northern colonies to the slave trade and examines the complicity of New England’s leading families, demonstrating how the region’s economy derived its vitality from the slave trading ships coursing through its ports.

Brethren by Nature: New England Indians, Colonists, and the Origins of American Slavery (2015) by Margaret Ellen Newell

In Brethren by Nature, Margaret Ellen Newell reveals a little-known aspect of American history: English colonists in New England enslaved thousands of Indians. Massachusetts became the first English colony to legalize slavery in 1641, and the colonists’ desire for slaves shaped the major New England Indian wars…

The Digital Archive of John Wompas. Jenny Hale Pulsipher, scholar and author of Swindler Sachem: The American Indian Who Sold His Birthright, Dropped out of Harvard, and Conned the King of England (Yale University Press, 2018) describes the archive below. Pulsipher’s notes on captives of King Philips War is where I first saw a “Mr Dudly” as enslaving an Indian girl; this was my first hint that any Dudleys had enslaved people.

I gathered a great deal of information on such subjects as Indian slavery, Native land sales, the Atlantic maritime trade, and Native education in Massachusetts. This information contributed to the book by providing historical context for Wompas’s life, but most nitty-gritty details were tangential to the book’s purpose so do not appear in it. Because those details could help other scholars working on more narrowly focused books or articles, I have placed them here where they can be accessible to anyone who has the URL.

Unfreedom: Slavery and Dependence in Eighteenth-Century Boston and Black Lives, Native Lands, White Worlds: A History of Slavery in New England by Jared Ross Hardesty. (See embeded WGBH video above.)

[Hardesty] shares the individual stories of enslaved people, bringing their experiences to life. He also explores the importance of slavery to the colonization of the region and to agriculture and industry, New England’s deep connections to Caribbean plantation societies, and the significance of emancipation movements in the era of the American Revolution.


HUB History Podcast: He Takes Faces at the Lowest Rates (episode 229) (2021) Host: Jake @HUBHistory

In 1773, an ad appeared in the Boston Gazette for a Black artist who was described as possessing an “extraordinary genius” for painting portraits.  From this brief mention, we will explore the life of a gifted visual artist who was enslaved in Boston, his friendship with Phillis Wheatley, the enslaved poet, and the mental gymnastics that were required on the part of white enslavers to justify owning people like property.  Through the life of a second gifted painter, we’ll find out how the coming of the American Revolution changed life for some enslaved African Americans in Boston.  And through the unanswered questions about the lives of both these men, we’ll examine the limits of what historical sources can tell us about any given enslaved individual.  

– HUB History

Hub History Podcast: Mutiny on the Rising SuMutiny on the Rising Sun, with Dr. Jared Ross Hardesty (episode 234) (2021) Host: Jake @HUBHistory

This week, Jake interviews Dr. Jared Ross Hardesty, author of the new book Mutiny on the Rising Sun: a tragic tale of smuggling, slavery, and chocolate, which uncovers the dark web of interconnections between Old North Church, chocolate, and chattel slavery.  Dr. Hardesty will explain why a reputable sea captain would become a smuggler, trafficking in illegal chocolate and enslaved Africans; the risks an 18th century Bostonian would take to provide himself with a competence, or enough money to allow his family to live independently; and what it meant in that era to be of but not from Boston.  At the heart of the story is a brutal murder and mutiny on the high seas, illustrating the fundamental brutality of life in the 18th century, but the role of the church (specifically Old North Church) in the social and economic lives of Bostonians is also central to understanding the life and death of Captain Newark Jackson.

– HUB History

Dynamic Digital Research Tools

Atlascope Boston, Norman B. Leventhal Map & Education Center at the Boston Public Library

HathiTrust Digital Library

Founded in 2008, HathiTrust is a not-for-profit collaborative of academic and research libraries preserving 17+ million digitized items. HathiTrust offers reading access to the fullest extent allowable by U.S. copyright law, computational access to the entire corpus for scholarly research, and other emerging services based on the combined collection. HathiTrust members steward the collection — the largest set of digitized books managed by academic and research libraries — under the aims of scholarly, not corporate, interests.
HathiTrust tutorial for researching their digital library, a source for many documents cited in this work.

Supplementary tweets from the Eleven Names Twitter account.

Three-tweet thread on potential lead on the post-Dudleian life of Brill.


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