Personal details about individuals held in slavery are precious. All historical records are incomplete, and this is even more true for those records documenting generations of people who were held in slavery. The glimpses we glean from letters, legal and financial documents, newspaper advertisements, and record books provide a stark vision of a world in which individuals were bought and sold in legal transactions to accommodate labor needs and debts. In these glimpses we also see—and we know deeply—that there are heartbreaking stories of spouses, and parents and children suffering separation from one another, or living under the constant threat of separation. The historical records shared below create the framework of sparse biographies of individuals held in slavery at Highland. You are invited to explore this collection and follow as we compile, organize, and add other entries.

It is difficult to choose language to describe enslavement. In the work on this page, we avoid referring to an individual as a slave, following the preference not to define a person by this legal status, preferring enslaved mother, son, or blacksmith, for example. The legally enforced status of slavery controlled so much of a person’s life, and we seek to recognize the humanity of each individual within that system. We use the terms bought, sold, and owned, employing them with the acknowledgment that even though these are everyday words, they are jarring when applied to humans as property. We should pause and reflect on all that is contained in these concepts.

Do you have information to add or share? Please contact us at info@highland.org.

Betsy Sanders

Born: about 1794
Died: after 1860
Family relationship: wife of Toby; mother to Augustus, Garrett, Jim, Sally, Judy, Kitty, Thomas, Peachy, Ceasar, Rosetta, and unknown
Role: unknown

Betsy was sold with her husband Toby and seven children in 1828 from Highland to Joseph White, owner of Casa Bianca plantation in Monticello, Florida. As many as six more children were born to Toby and Betsy at Casa Bianca. After emancipation, their descendants took the last name Sanders.

Billy

Born: unknown
Died: after 1822
Family relationship: unknown
Role: carpenter

Billy first appears at Highland on an 1810 blanket distribution list. In an 1822 letter between Monroe and an overseer, Billy is described as a carpenter who can construct complex agricultural equipment. It is not known what happened to Billy after the sale of Highland.

Charles

Born: before 1790
Died: after 1828
Family relationship: Son of Dick and Hannah; brother to Dick, Wilson, Spotswood, Jesse, Nelson, a sister (name unknown) and two younger brothers (names unknown)
Role: unknown

Charles was enslaved by Charlottesville resident Peter Marks, who purchased property from James Monroe in 1790 and mortgaged 33 individuals as part of the agreement. Marks died in 1795 before paying his debt to Monroe. Charles was then purchased for James Monroe by his uncle, Judge Joseph Jones, while Monroe was abroad serving as Minister to France. He was sold locally in Virginia between late 1827 and early 1828. This local sale meant that Charles was not part of the group sale from Highland to the Florida territory in 1828.

Daniel

Born: unknown
Died: unknown
Family relationship: unknown
Role: unknown

Daniel was physically assaulted while rented out by Monroe to Albemarle County planters Joseph Brand and Thomas Jefferson Jr. (nephew of Thomas Jefferson through his brother Randolph Jefferson), causing James Monroe to sue for property damage.

Dudley McGuire

Born: before 1809
Died: after 1844
Family relationship: husband of Eve; father of William, Hannah, Patsy, Jane, Ellen and Richard
Role: unknown

Dudley was enslaved by Monroe’s uncle, Judge Joseph Jones, in Loudoun County, Virginia until his death in 1805, and then by Jones’ son until 1809 when he was transferred from Jones’ estate to James Monroe through an intermediary, Charles Love. He was sold with his wife Eve and their two children in 1828 from Highland to Joseph White, owner of Casa Bianca plantation in Monticello, Florida. Dudley and Eve appear to have had four more children in Florida. Dudley was enslaved for at least sixteen years at Casa Bianca (1828-1844), but does not appear on any subsequent inventories after the year 1844.

Eve McGuire

Born: about 1800
Died:  after 1870
Family relationship: Wife of Dudley; mother of William, Hannah, Patsy, Jane, Ellen and Richard
Role: unknown

Eve was sold with her husband Dudley and two children in 1828 from Highland to Joseph White, owner of Casa Bianca  plantation in Monticello, Florida. Eve and Dudley appear to have had four more children at Casa Bianca plantation. After emancipation, Eve was listed as living with her youngest son Richard in Jefferson County, Florida in the 1870 census, both listed under the last name “McGuire.”

Garrett Sanders

Born: based on the 1870 census, about 1810
Died: after 1870
Family relationship: Son of Toby and Betsy; brother of Augustus, Jim, Sally, Judy, Kitty, Thomas, Peachy, Ceasar, Rosetta, and unknown.
Role: unknown at Highland; later a blacksmith at Casa Bianca plantation in Florida

Garrett was born into slavery at Highland and sold as a teenager with his family in 1828 to Joseph White, owner of Casa Bianca plantation in Monticello, Florida. Garrett was later documented as a blacksmith at Casa Bianca. After emancipation he took the last name Sanders. Garrett purchased property in Taylor County, Florida and registered to vote in 1867.

George

Born: about 1796
Died: unknown
Family relationship: Husband of Phebe
Role: laborer

George and his wife Phebe ran away from Highland the night of Monday July 3, 1826. It is likely that George or Phebe had previously spent some time at Monroe’s Oak Hill property in Loudoun County, Virginia since the ad presumes “they are supposed to be making for the county of Loudon [sic].” The couple’s fate is unknown.

George Williams

Born: about 1786
Died: after 1836
Family relationship: Husband of Ann Williams; father of two children (names unknown)
Role: “plantation hand,” assisted with carpentry

It is likely George Williams helped construct the surviving guesthouse at Highland, alongside enslaved carpenter Peter Malorry. While Monroe owned more than one George, George Williams is the only documented George of an appropriate age to build the guesthouse in 1818. He is also the only George documented within four years of its construction. It’s apparent from inventories and correspondence that George Williams was primarily at Oak Hill in Loudoun County, Virginia, but was temporarily moved to Highland during late summer 1818 for the purpose of building new structures for Monroe.

Hannah

Born: unknown, she was an adult by 1790
Died: after 1803
Family relationship: Wife of Dick; mother to Dick, Wilson, Jesse, Spotswood, Charles, a daughter (name unknown), three younger sons (names unknown, although “Nelson” is later listed as being a brother to Jesse and Charles in an 1825 deed)
Role: Cook

Hannah was enslaved as part of the estate of Charlottesville resident Peter Marks, who purchased property from James Monroe in 1790 and mortgaged 33 individuals as part of the agreement. Marks died in 1795 before paying his debt to Monroe. Hannah and some of her children were then purchased for James Monroe by his uncle, Judge Joseph Jones, while Monroe was abroad serving as Minister to France. Jones had attempted to purchase Hannah’s whole family, but her husband Dick had an arrangement to work out his freedom with another buyer; her sons Dick and Wilson were also purchased by others ahead of Jones.

James (or Jim) Sanders

Born: about 1825
Died: after 1870
Family relationship: Son of Toby and Betsy; brother of Augustus, Garrett, Sally, Judy, Kitty, Thomas, Peachy, Ceasar, Rosetta, and unknown; husband of Lucy; father of Katy, Garrett, Ann, and Elijah
Role: Child

James was born into slavery at Highland and then sold around the age of three with his family in 1828 to Joseph White, owner of Casa Bianca plantation in Monticello, Florida. After emancipation he took the last name Sanders.

Jesse

Born: before 1790
Died: after 1825
Family relationship: Son of Dick and Hannah; brother to Dick, Wilson, Spotswood, Charles, Nelson, a sister (name unknown) and two younger brothers (names unknown)
Role: Laborer; worked with cattle

Jesse was enslaved by Charlottesville resident Peter Marks, who purchased property from James Monroe in 1790 and mortgaged 33 individuals as part of the agreement. Marks died in 1795 before paying his debt to Monroe. Jesse appears to already be enslaved at Highland before Marks’ estate sale took place in January 1796, as referenced by Monroe’s uncle noting “…it is indispensably necessary to add to Solomon his wife and Jesse at Hogs some others if to be got” (Joseph Jones to James Monroe, 16 January 1796). It is not known what happened to Jesse after Highland was sold.

Joe

Born: unknown
Died: after 1825
Family relationship: Husband of Eve; father to four children (names unknown)
Role: unknown

Joe was included with his wife and four children in an 1825 mortgage between James Monroe and the Farmer’s Bank of Alexandria. He appears to have been enslaved at Highland for at least sixteen years before the mortgage (1809-1825). It is not known what happened to Joe and his family after the sale of Highland.

Mary Hemings

Born: before 1793
Died: after 1803
Family relationship: Daughter of Thenia Hemings; sister of Lucy, Betsy, Susan, Sally and sibling born in 1795 (name and gender unknown)
Role: unknown

Mary Hemings was sold as a child to James Monroe in 1794, along with her mother Thenia (1767-1796) and four sisters. Initially, Mary and her family lived at Monroe’s property in Charlottesville which would eventually become the University of Virginia. After the death of Thenia Hemings in 1796, Mary and her sisters appear to have remained enslaved to the Monroes, likely residing either at the Charlottesville property or Highland. In 1801, Governor Monroe sold Mary to Samuel Coleman, resident of Henrico County and Assistant Clerk of the Council of State of Virginia. Two years later in 1803, Coleman manumitted Mary Hemings. Mary’s fate following manumission is unknown.

Nancy Green

Born: about 1761
Died: after 1836
Family relationship: Wife of Solomon Green
Role: unknown

Nancy Green and her husband Solomon were held in bondage by James Monroe – and after Monroe’s death in 1831, by his heirs – for over 40 years. It is not known when Monroe purchased Nancy or her husband Solomon, but they are mentioned as already being enslaved at Highland prior to 1796. It is assumed Nancy and Solomon are among the individuals Monroe spoke of when he wrote after the sale of Highland that he planned “the removal of some old servants, too old to be sold, to this place [Oak Hill] to be taken care of by us.” (James Monroe to Thos. Swann, 19 May 1828). Nancy’s and Solomon’s names are listed together on an 1836 inventory at Oak Hill (property Monroe owned in Loudoun County, Virginia) after Monroe’s death.

Nelson

Born: around 1790
Died: after 1828
Family relationship: Son of Hannah and Dick; brother of Dick, Wilson, Spotswood, Jesse, Charles, a sister (name unknown) and two other brothers (names unknown)
Role: Blacksmith

Nelson was born enslaved to Charlottesville resident Peter Marks, who purchased property from James Monroe in 1790 and mortgaged 33 individuals as part of the agreement. Nelson’s mother Hannah was purchased as a cook for the Monroes in 1796, along with Nelson and her two other young sons. The older sons, Spotswood and Charles, were also purchased by Monroe, either at this time, or later. Jesse, a sixth son, was already at Highland with overseer Hogg, in plantation operation before the Monroes took up residence. Nelson was described as a blacksmith in an 1825 mortgage. He was sold locally between late 1827 and early 1828. This local sale meant that Nelson was not part of the group sale from Highland to the Florida territory in 1828.

Peter

Born: unknown
Died: after 1796
Family relationship: unknown
Role: Gardener

Peter is one of the earliest documented individuals held in bondage by the Monroes. Peter first appears in documents during the Monroes’ early marriage in Fredericksburg, Virginia, a few years before they established residency in Albemarle County in 1789. Peter traveled independently and is referenced at Monroe’s Charlottesville property that would later become the University of Virginia, as well as at Highland.

Peter Malorry

Born: about 1764
Died: after 1836
Family relationship: Husband of Charity
Role: Carpenter

Peter Malorry was an enslaved carpenter purchased by James Monroe in late 1817 from Judge Francis Taliaferro Brooke, who was living at St. Julien in Spotsylvania County, Virginia. Documentary evidence shows that Peter Malorry built the standing guesthouse at Highland with another enslaved man named George. It’s apparent from inventories and correspondence that Peter Malorry was primarily at Oak Hill in Loudoun County, Virginia, but was temporarily moved to Highland during late summer 1818 for the purpose of building new structures for Monroe.

Peter Marks

Born: around 1795
Died: 1860
Family relationship: Husband of Eugenia Hemings Marks; father of James, Mary Ann, Eugene, Elizabeth, Edward
Role: manservant; coachmen

Peter Marks is the only enslaved individual known to be freed by James Monroe. According to a Monroe family friend, Peter was in “the family of Mr. Monroe from his … [yout]h” and described as an “excellent dining room ser[van]t; and a good coachman.” (Letter of Recommendation by Tench Ringgold, 27 August 1831). Peter’s parentage is unknown, but two women enslaved by the Monroes are known to have born a child in 1795, the approximate year of his birth: Thenia Hemings as well as the cook Hannah.

Phebe

Born: about 1798
Died: unknown
Family relationship: wife of George
Role: unknown

Phebe and her husband George ran away from Highland the night of Monday July 3, 1826. It is likely that Phebe or George had previously spent some time at Monroe’s Oak Hill property in Loudoun County, Virginia since the ad presumes “they are supposed to be making for the county of Loudon [sic].” The couple’s fate is unknown.

Roger

Born: unknown
Died: unknown
Family relationship: Husband of unknown enslaved woman sold South at Carter Braxton’s estate sale on January 30, 1810
Role: Manservant

Roger was purchased by James Monroe from the estate of Carter Braxton on January 30, 1810. Monroe wrote that he’d purchased Roger “for my own accommodation,” so Roger was likely an enslaved manservant (James Monroe to Fulwar Skipwith, 9 October 1810). Roger’s wife had been “sold to some one to the South at the same time” at the sale Monroe attended, and Roger had communicated to Monroe that he was “desirous of going that way in hope they might finally meet again” (James Monroe to Fulwar Skipwith, 9 October 1810). It is unknown if Roger was able to find his wife after being sold by Monroe to Fulwar Skipwith in New Orleans.

Solomon Green

Born: about 1771
Died: after 1836
Family relationship: Husband of Nancy Green
Role: Laborer

Solomon Green and his wife Nancy were held in bondage by James Monroe – and after Monroe’s death in 1831, by his heirs – for over 40 years. It is not known when Monroe purchased Solomon or his wife Nancy, but they are mentioned as already being enslaved at Highland prior to 1796. It is assumed Solomon and Nancy are among whom Monroe spoke of when he wrote after the sale of Highland that he planned “the removal of some old servants, too old to be sold, to this place [Oak Hill] to be taken care of by us.” (James Monroe to Thos. Swann, 19 May 1828)  Solomon and Nancy’s names are listed together on an 1836 inventory at Oak Hill (property Monroe owned in Loudoun County, Virginia) after Monroe’s death.

Spotswood

Born: before 1790
Died: unknown
Family relationship: Son of Dick and Hannah; brother to Dick, Wilson, Jesse, Charles, Nelson, a sister (name unknown) and two younger brothers (names unknown)
Role: unknown

Spotswood was born enslaved to Charlottesville resident Peter Marks, who purchased property from James Monroe in 1790 and mortgaged 33 individuals as part of the agreement. Marks died in 1795 before paying his debt to Monroe. Spotswood was purchased for James Monroe by his uncle, Judge Joseph Jones, while Monroe was abroad serving as Minister to France.

Sukey

Born: unknown
Died: after 1801
Family relationship: unknown
Role: Spinner

Sukey was an enslaved spinner whose agency enabled her to change her living situation. While James Monroe was abroad serving as Minister to France (1794-1797), his younger brother Joseph was managing his property that would later become the University of Virginia. Sometime after Monroe’s departure, Sukey and Joseph had a “quarrel.” Monroe’s uncle, Judge Joseph Jones, mediated between Sukey and Joseph, first moving her to the residence of “Jones in Town,” then contemplated selling her or moving her to Highland (Joseph Jones to James Monroe, 16 January 1796). Later references in Monroe’s account book show purchases on Sukey’s behalf, indicating the plan to have her “live at Hogs to work for him & people and spin” must have been carried out (Joseph Jones to James Monroe, 16 January 1796).

Toby Sanders

Born: about 1789
Died: after 1860
Family relationship: husband of Betsy; father to Augustus, Garrett, Jim, Sally, Judy, Kitty, Thomas, Peachy, Ceasar, Rosetta, and unknown
Role: unknown

Toby was enslaved by Monroe’s uncle, Judge Joseph Jones, in Loudoun County, Virginia until his death in 1805, an then by Jones’ son until 1809 when he was transferred from Jones’ estate to James Monroe through an intermediary, Armistead T. Mason. He was sold with his wife Betsy and seven children in 1828 from Highland to Joseph White, owner of Casa Bianca plantation in Monticello, Florida. As many as six more children were born to Toby and Betsy at Casa Bianca. After emancipation, their descendants took the last name Sanders.

William McGuire

Born: about 1825
Died: unknown
Family relationship: Son of Dudley and Eve; brother of Hannah, Patsy, Jane, Ellen, and Richard; husband of Bella; father of Bill, Rhoda, Moses, Minty, Rebecca and Georgeann.
Role: child

William was born into slavery at Highland and sold as a three year old with his family in 1828 to Joseph White, owner of Casa Bianca plantation in Monticello, Florida. Later documentation shows he took the last name McGuire and helped found Casa Bianca Missionary Baptist Church in Monticello, Florida.