Dudley and Eve McGuire – William McGuireDavid Straws, Sr.Toby and BetsyGarrett SandersJames SandersPeyton PleasantsHope DouglasIsham NelsonFrank NelsonMary BakerCharles and Ann TysonJim and Calypso HarrisHenry Clay WhiteMaria White Williams – Garland Monroe

Dudley and Eve McGuire (b. 1800) were sold with their two children from James Monroe’s Highland plantation to Florida. Their family continued to increase in Florida, eventually encompassing six children: William, Hannah, Patsy, Jane, Ellen, and Richard. Dudley died sometime before 1848; his name does not appear on any other plantation documents after that date. Eve most likely was an enslaved domestic for Ellen at Casa Bianca, as Eve was shipped from New Orleans to Florida in 1858, suggesting that she travelled with Ellen. This evidence also suggests that Eve may have been the enslaved woman referred to in the account books for President Monroe at the White House during his first term in office. Both an Eve and Betsy are named in Monroe’s White House accounts.

Eve McGuire with her youngest son, Richard. 1870 U.S. Federal Census, Jefferson County, Florida, pop. sch., Monticello Post Office, Township 6, p. 1, dwelling 11, family 11, Richd McGuire household.

After emancipation, Eve lived with her youngest son Richard, dying sometime after 1870. Dudley and Eve’s legacy, though mostly undocumented while enslaved, continued with their descendants, who had the surname McGuire. Their children played a founding and integral role in the 1873 establishment of the Casa Bianca Missionary Baptist Church in Monticello, Florida.

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William McGuire was the eldest son of Dudley and Eve. Born in Albemarle County, Virginia around 1825, he was about three years old when President James Monroe sold him and his family to Florida. At Casa Bianca, he married Bella and they had four known children while enslaved: Bill, Rhody, Moses, Minty. Their daughters Rebecca and Georgeann were born after emancipation. In 1860, William, his wife and four children were sold by Ellen Beatty to Tallahassee lawyer Robert Williams. In a subsequent deed between Williams and Beatty, Williams promised to “insure the lives of said negroes for and during the voyage from Florida to the said William’s Landing on the Mississippi River in Louisiana.” Evidence suggests that William and his family went to Louisiana. According to the 1880 census, his daughter Rebecca was born there in 1865, and his oldest son Bill, also known as William, was in St. James Parish, Louisiana in the 1870 and 1880 census. Another son, Moses, was also in St. James Parish in 1880. To date, the 1870 census listing William McGuire has not been found, but by the early 1870s, they were in Jefferson County, where his daughter Georgeann was born around 1872. The next year, William was one of the trustees who purchased the land for the Casa Bianca Missionary Baptist Church. He purchased his own acre of land for $25 in 1884. William disappeared after the 1885 Florida census, but his wife Bella was still living with her grandchildren in Jefferson County in 1900, owning her home mortgage free.

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David Straws, Sr., born in Kentucky and enslaved at Casa Bianca, was part of his slaveholder Ellen White’s life estate. David married Dudley and Eve’s daughter Hannah. After emancipation, David Straws became the first pastor of the Casa Bianca Missionary Baptist Church.

David Straws Sr.’s signature from a marriage certificate.

David Straws continued to farm Casa Bianca land, making his mark on a labor contract to work six days a week and supply the owner, C.S. Taylor, with one-third of the crops he grew. He was later given an acre of Casa Bianca land by Theodore Becker, a German immigrant who had purchased 10 acres of Casa Bianca in the 1880s.

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Toby (born circa 1789) and Betsy (born circa 1794) were an enslaved couple held in bondage by President James Monroe, living and working at his Highland plantation in Albemarle County, Virginia. In 1828, Monroe sold Toby and Betsy and their seven children (to date, five of their children, Augustus, James, Garrett, Peachy and Kitty, have been identified as born in Virginia) to Joseph M. White of Florida. Toby and Betsy made the forced journey to Jefferson County, Florida, where they labored on the Casa Bianca plantation. As one of the older enslaved women at Casa Bianca, Betsy may have spun and wove the wool from Casa Bianca’s sheep. On the eve of the Civil War, Toby, Betsy, and their son Caesar, were sold to Tallahassee lawyer Robert Williams. This 1860 bill of sale was the last document in which we find Toby and his wife Betsy. Their descendants have the surname Sanders after emancipation.

It is possible that Betsy was the daughter of Thenia Hemings, who was sold along with her children by Thomas Jefferson to James Monroe in 1794. Thenia and her daughters Lucy, Betsy, Susan, and Sally were listed in Jefferson’s Farm Book (p. 25, 19 September 1794). While enslaved by Monroe, Thenia had another child whose gender is unknown. Thenia died soon after, never having completely recovered from childbirth. Betsy Sanders’ birthdate corresponds to Betsy Hemings’ birth. Two of Betsy Sanders’ children are also named James and Sally, names used often by the Hemings family. DNA testing of Betsy Sanders’ descendants can confirm if there is a Hemings family connection.

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Garrett Sanders  was the enslaved blacksmith at Casa Bianca. One of the sons of Toby and Betsy, as a boy he lived at James Monroe’s Highland plantation in Virginia and was sold along with his parents and siblings to Joseph White in 1828, when he was around eighteen years old. While at Casa Bianca, Garrett would have been responsible to making and repairing plantation tools, such as hoes and plows, and other hardware in use at the plantation. Garrett’s enslavers also hired him out to work for other local plantations. After emancipation, Garrett moved to nearby Taylor County with his brother James and sister Peachy and their families. He continued his occupation, appearing as a blacksmith in the 1870 census with $800 of personal property, making him the African-American with the most property in the county. Out of 227 people recorded with personal or real estate property, Garrett ranked #15. In August 1867, while living in Taylor County, he registered to vote in the first Florida election in which a freedman could participate.

Garrett Sanders
Garrett Sanders’ Voter Registration, Taylor County, Florida

In the early 1870s, the Sanders families moved back to Jefferson County where Garrett, identified as a Radical Republican, voted in the 1876 presidential election. He continued to work as a blacksmith and also farmed. His widowed sister Peachy and her children lived with him. Five years later, Garrett lived with his grandniece and grandnephew (His sister Peachy disappeared from written records after 1880). Garrett last appeared in any document in 1885.

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James, or Jim, Sanders was another son of Toby and Betsy born in Virginia. He lived at James Monroe’s Highland plantation until the sale of his parents and siblings in 1828 when he was around eight years old. At Casa Bianca, James most likely labored as a field hand, clearing the fields for planting and harvesting the crops of cotton, sugar cane, and corn. After emancipation, he and his wife Lucy, with their four children, Katie, Garrett, Ann, and Elijah, moved to nearby Taylor County. By January 1873, the family returned to Jefferson County, where James rented nineteen acres of land from a local planter. In 1885, he rented thirty-five acres of land, producing 150 bushels of corn, 50 bushels of sweet potatoes, and 7 bales of cotton. By 1900 James had his own farm, which was mortgage free a decade later.

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Peyton Pleasants Peyton Pleasants was born at Casa Bianca around 1842. His mother was Lucy, the only female captive of the slave ship The Antelope purchased by Richard Wilde. Peyton was also identified as the grandson of Toby and Betsy, who James Monroe sold to Florida in 1828. In 1860 the owner of Casa Bianca, Ellen White, sold Peyton to her nephew J. Patton Anderson, who had been managing the plantation for nearly five years. Anderson joined the Confederate Army and ultimately rose to Brigadier General. He took Peyton, who may have already been Anderson’s personal servant at Casa Bianca, with him to continue in that capacity. In 1863, Anderson wrote back to his wife Etta that he had to find a replacement for Peyton, who had now been assigned to be the permanent company cook.

J. Patton Anderson to Etta Anderson, Nov. 9, 1863. J. Patton Anderson Papers, University of Florida.

After emancipation, Peyton took the surname Pleasants and worked as a sharecropper on Anderson’s “The Scrub” land – 400 acres southeast of Monticello. He married Mary Lawton in 1867 and together they had four children: Milly, Paul, Peyton, and Abe. We lose track of Peyton in the 1890’s. His wife Mary purchased a Monticello town lot in 1892, on the northern edge of what became known as Rooster Town, the African-American section of Monticello.

Mary Pleasant’s lot. Jefferson County, Florida, Deed Record V:589.

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Hope Douglas was born in Georgia sometime between 1796 and 1805. Legally the property of William McGahagin of Effingham County, Georgia, McGahagin gave Hope to his daughter Margaret when she married William McCardell in 1821. The only enslaved person in the McCardell’s household, Hope would have performed domestic labor – cooking, cleaning, laundry, sewing, and caring for the McCardell’s children. By 1830 Hope had three children of her own – Bob, Frank, and Isham (unfortunately, their father’s identity is unknown at this time). The McCardells moved to Monticello, Florida around 1832, bringing Hope and her children with them and promptly mortgaging them for debts. At some point, McCardell owed money to Everett White, Joseph M. White’s brother and manager of Casa Bianca. When McCardell did not pay, Everett forcibly took Hope and her children away from McCardell, putting them to work at Casa Bianca. When Everett died, Hope, Bob, Frank, Isham and her youngest child William (born in Florida) were sold on the Monticello courthouse steps to pay for Everett’s outstanding debts. Everett’s brother Joseph purchased them. Hope and her children remained at Casa Bianca until 1860, when Joseph White’s widow Ellen sold them along with nearly 80 other enslaved people to Tallahassee lawyer Robert W. Williams. By this time, Frank had married Kitty, a daughter of Toby and Betsy, while Isham had married Jane, a daughter of Dudley and Eve. This sale separated families, as Hope, Frank and his family were shipped to Williams’ plantation in Louisiana. Isham and his family remained in Florida. The 1880 census is the last record found with Hope – at the age of 100, she was living near her sons Frank and Richard and her grandchildren and great-grandchildren in Chicot County, Arkansas.

Hope Douglas near her sons Richard and Frank, along with her grandchildren Clarissa and Frank, Jr., and her great-grandchildren. 1880 U.S. Federal Census, Chicot County, Arkansas, pop. sch., Louisiana Township, ED 27, p. 9A, household 108, family 113.

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Isham Nelson was born around 1832. He was the son of the enslaved woman Hope. Isham, Hope, and his brothers Bob, Frank, and William were held in bondage by Joseph White’s brother Everett, who served as Casa Bianca’s overseer until his death in 1835. After Everett White’s death, the family was sold at the Monticello courthouse. Their buyer, Robert Rose, then sold the family back to Joseph White. Sometime after 1844, Isham married Jane McGuire, the daughter of former Monroe slaves Dudley and Eve. Together, they had five children before emancipation (William, Rose, Robert, Clement, and Isaiah) and two children after emancipation (George and Eliza). Isham, his mother and brother, along with his nieces and nephews, all lived and worked at Casa Bianca until the plantation was sold, along with them, in 1860. The sale split apart Isham’s family – his mother and brothers Richard and Frank, with Frank’s family, were sent to a Louisiana plantation. Isham never saw or heard from them again. Isham and his family remained in Jefferson County after emancipation. His wife Jane died after 1870, and Isham remarried a woman named Lucretia before 1880. In 1873, Isham helped establish a church that continues to hold services today. He, along with his brother-in-law William McGuire, were two of the founding trustees of the Casa Bianca Missionary Baptist Church. One of his descendants, Willie Nelson, was a deacon of the church when it was rebuilt in 1972, and Isham’s great-granddaughter was the longest serving member of the church until her death a few years ago.

Casa Bianca Missionary Baptist Church

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Frank Nelson was the son of Hope Douglas. Born in Georgia, he came to Florida with his mother and siblings when their slaveholder moved to Monticello around 1832 (see Hope Douglas entry for details of his childhood). Frank married Kitty, one of the children sold by James Monroe in 1828 and a daughter of Toby and Betsy. Together, Frank and Kitty had four children – Archie, Frank, Jr., Louisa, and Clarissa. The family was shipped to Louisiana after Casa Bianca was sold in 1860, where they worked on Robert Williams’ Panola plantation on the Mississippi, one of the largest cotton producing plantations in the state.

Detail of map showing location of Williams’ plantation, north of Lake Providence in modern East Carroll Parish. Source: Mcfarland, A. Map of plantations in Carrol sic Parish, Louisiana and Issaquena County, Mississippi. [Skipwith, Miss.: ?, 1860] Map.

After emancipation, Frank and his sons Archie and Frank, Jr. made their marks on a labor contract to work at the Ames plantation in East Carroll Parish.

Frank Nelson’s and his son’s, Archie and Frank, Jr., marks on a labor contract, 17 February 1868. Source: Louisiana Freedmen’s Bureau Field Office Records, Labor contracts (agreements with freedmen): Caldwell and Carroll, 1866-1868 [NARA M1905 roll 42].

By 1880, the Nelsons moved to Chicot County, Arkansas, just north of East Carroll Parish, where Frank owned his farm mortgage free according to the 1900 census.

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Mary Baker. The Bakers were an enslaved family owned by James Monroe’s son-in-law George Hay. In 1826 Mary Baker’s mother Sally sued Charles Hay, George’s son from his first marriage, for her and her children’s, Mary and Jeffry, freedom. The court rejected her petition, and George Hay promised to pay Sally’s court fees and forgive and forget her past actions if she agreed to return with him to his Virginia home. A year later Hay gave Sally, her son Jeffry (Geoffry in the deed), and Sally’s latest child Nicholas to his daughter by his first marriage (and Charles’ sister) Maria Antoinetta Ringgold (note: the deed says that Hay originally purchased Sally from the estate of Miles Seldon [of Richmond]). Hay’s promise to forgive and forget Sally’s past actions evidently didn’t extend to her daughter Mary Baker and she was included in the sale to Joseph M. White in 1828. Her full name appeared on the 1844 Casa Bianca deed, one of two enslaved people with recorded surnames at the plantation. Hester, Caroline, Claibourne, and another daughter named Evaline were her children.

Mary Baker in the 1844 Casa Bianca Deed. Source: Jefferson County, Florida, Deed Record E:113.

It is likely Mary and her children went to the Bellamy estate to satisfy the 1844 mortgage, as none of them are found on later Casa Bianca documents and as her daughter Caroline’s marriage to James Mickens was registered on the Waukeenah plantation, which had been a Bellamy property. After emancipation, Mary continued to reside in Jefferson County, first living with her daughter Caroline and family (1870 census) before working as a servant in a family and living with her grandson Major Munroe in the 1880 census. She was identified as a widow, and the name of her spouse is unknown at this time. Mary Baker died in December 1884. Mary’s daughter Caroline purchased two acres of land in 1884. Caroline’s son Clayborn purchases another eighty acres in 1888, which is still owned by descendants today. Two of Mary Baker’s great-great-grandsons, Sumpter and Wade Tyson, served in the US Army during WWII.

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Charles and Ann Tyson (b. abt. 1805) were enslaved domestic servants at Casa Bianca along with their children Rebecca (b. bet. 1822-1828), William, Alice, Hannah (b. abt. 1833) and Lewis. The family was most likely born in Virginia, and Rebecca stated that she and her parents were born in Washington, D.C. (1880 census). It is unknown when the Whites acquired the Tysons; it may have been during one of the Congressional sessions attended by Joseph M. White. As enslaved domestics, the Tysons would have been close to Ellen Adair White Beatty, her niece and nephew (Henrietta and James Patton Anderson), and their children. Rebecca was Ellen’s personal maid and accompanied her on her travels while Alice was Ellen’s great-nieces’ and nephews’ enslaved nurse. Letters from J.P. Anderson asked for his regards to be given to “Charles & Aunt Ann, Rebecca & Alice.” When Anderson took over management of the plantation in early 1856, Ellen reserved management of the Tysons for herself. Charles did not appear in any documents after emancipation, but Ann lived with her daughter Rebecca and son-in-law Henry Clay White in the 1870 census.

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Jim and Calypso Harris were an enslaved couple owned by President James Monroe and primarily associated with his Oak Hill plantation in Loudon County, Virginia, where they were listed with the surname Harris on an 1823 plantation inventory and tools list, along with an unnamed child. Sold to Joseph M. White in 1828, they appeared in an 1844 deed for Casa Bianca plantation, which also included the surname Harris. Jim Harris and Mary Baker were the only enslaved people in Casa Bianca records with a recorded surname. The 1844 deed was the only Casa Bianca document on which Jim and Calypso appear together, and though an enslaved man named Jim was listed in later records, Calypso’s name was missing from documents. No papers have been found suggesting their sale away from Casa Bianca. They remained in the county after emancipation, as Calypso lived with her son Anthony and his wife in the 1880 census. Jim Harris signed his mark as a witness on the freedmen’s contract that was made for Peyton Pleasants and brothers Absolom and Moses Lemons, who had also been enslaved at Casa Bianca.

Marvin, J.M. Contract Between J.M. Marvin & Thomas Harris, William Marks, 1867-03-30. State Archives of Florida, Florida Memory.

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Henry Clay White was the son of the enslaved woman Fanny. Born in Kentucky around 1830, Everett White, Joseph M. White’s brother and Casa Bianca’s manager, brought Henry Clay along with Fanny and his siblings from Kentucky to Florida. The family may have had a special status apart from the others enslaved at the plantation, as Everett’s will directed that Fanny and her children were to be freed upon his death and taken back to Kentucky. But Everett’s estate was deeply in debt, and Henry Clay’s sister Amanda was sold at the Monticello courthouse to another county farmer. Almost a decade later, Fanny, Henry Clay, and his sister Aggie and brother Uncas were sold to Ellen White’s second husband, Theophilus Beatty. In 1852, in one of the few recorded marriages between enslaved people in the county, Henry Clay married Rebecca, the daughter of Charles and Ann Tyson. The Rev. A.W. Clisby, the Presbyterian minister Ellen Adair White Beatty had hired for the plantation, performed the ceremony. After emancipation, Henry Clay White and Rebecca purchased a lot in downtown Monticello for $700, the first land purchase by a formerly enslaved family from Casa Bianca. He signed the deed with his signature, indicating that he was literate, whereas his wife Rebecca made her mark on the contract. In 1869 he paid taxes on four horses and two carriages, which suggests he may have been a driver and hired himself out. This also hints at his occupation while enslaved at Casa Bianca. A few years later, Henry Clay White owned not only the Monticello town lot but also eighty acres of land south of town; he paid the second highest amount of taxes for an African-American in the county. In 1867 he was a trustee of the Howard Freedmen’s School Association, which purchased land in Monticello.

Detail of Henry Clay White’s signature from letter to Freedmen’s Bureau. Source: Henry Clay et. al. Trustees of “Howard Freedmen’s school association,” 19 October 1867, Records of the Assistant Commissioner and Subordinate Field Offices for the State of Florida, Bureau of Refugees, Freedmen, and Abandoned Lands, 1865-1872, Monticello, Letters Received, May 1866 – May 1868 (National Archives Microfilm Publication M1869, roll 15).
Detail of Bird’s-Eye View of Monticello, 1885, showing location of Henry Clay White’s Monticello town lot and the location of the Howard Freedmen’s School. Source: State Library of Florida, Florida Map Collection, Geographic Area Bird’s Eye View Monticello 0001.

Henry Clay White’s wife Rebecca died between 1880 and 1885. They didn’t have any recorded children. He married Kate Sanders, the daughter of James and Lucy Sanders and granddaughter of Toby and Betsy. Together they had eight children, five of whom were living with Kate in 1900: James, Delia, Sallie, Henry, and Theodore . Henry died sometime before 1900.

A note on the Howard Freedmen’s School. As can be seen from the date of the map above, this school was still in existence in 1885, almost 20 years after the Association purchased land for it. It no longer stands, and a modern church now sits at its location. In 1936 another school was founded in Monticello, the Howard Academy, which later became the Howard Middle School. The original Howard Academy building in Monticello still exists and its restoration is the focus of the Howard Academy Educational & Recreational Council, Inc. (The early school was most likely named after Oliver Otis Howard, a Union Army general who was put in charge of the Freedmen’s Bureau in 1865, and it seems probable that the later schools carried this tradition forward.)

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Maria White Williams was born around 1806. She was 18 when White shipped her, her mother Mary, and her brother Wilson from New Orleans to Pensacola in 1827. She was an enslaved domestic for Joseph and Ellen White, and they took her with them to Washington, D.C. for the December 1828 Congressional session. In Washington Maria met and married a free black man, and they soon expected a child. White had planned to take her back with him to Florida at the end of the Congressional session, but due to her advanced state of pregnancy, he left her in Washington and allowed her to hire herself out and keep her wages. Maria also asked White if he would sell her to her husband for $400. White agreed, but Maria and her husband were unable to raise the funds. Maria then sued White for her freedom and that of her new son, Richard Henry Williams, claiming that he brought her into the capital to sell her, which was against the law. The court ruled against Maria. Four months later, White manumitted Maria and her son for the payment of $1. There is one family in the 1830 Washington, D.C. census that matches the description of Maria, her son, and her husband: the household of free black Henry Williams. Is this Maria’s husband? Research is still ongoing to determine what happened to Maria and her son Richard Henry after their emancipation.

Jury instructions from O Say Can you See: Early Washington, D.C., Law & Family, “White, Joseph M., 1781-1839,” accessed December 17, 2017,
James Garland Monroe Sr.
Garland Monroe

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Garland Monroe, whose father once belonged to President James Monroe, says that slaves used to meet in the mountains near Monticello, out from Charlottesville.  “I’m gittin’ on to ninety, but I recollec’ my daddy an’ two older brothers slippin’ out nights to go to meetin’. Brothers would tell me all ’bout it nex’ day. Dey had what dey called a stump preacher;ole man Tucker Coles it was. Dey call him a stump preacher ’cause he used to git up on a stump an’ preach to de slaves—you see, up dere’ rounst Monticello ole patterollers would keep away, so de slaves ain’t bothered to build a hut an’ put pots all roun’ like dey did in some places. Jus’ preached right in de open, an’ if de patterollers come, dey would jus’ run down de mountain side ‘long paths dat de patterollers didn’t know nothin’ ’bout.Well, once patterollers did break up a meetin’. My brothers tell me all ’bout it de nex’ day. Ole Tucker Cole was jus’ a-preachin’ ‘way an’ shoutin’ when dey hear patterollers creepin’ in de bush close by. Slaves started runnin’ down de mountain side, not too fas’, jus’ fas’ ‘nough to keep de patterollers chasin’ ’em. My brother, Henry,went on runnin’ ahead o’ de res’. Down at de foot of de mountain was a creek. “Hardware Creek,” was its name, an’ dere was log laid ‘cross it so’s you could git to de other side widdout gittin’ wet. My brother got down dere ‘fore all de res’ an’ stuck a slice-bar under one end of de log, an’ den dere come de patterollers. Henry was hid ‘hindst de bushes, an’ when de fus’ two three patterollers git to walkin’ careful-like in de middle of de creek, Henry took an’ pried up dat log an’ thowed ’em all in de water. Patterollers yelled an’ cussed de slaves somep’n terrible, but time dey got dey clothes wrung out de slaves was home in bed.”

From The Negro in Virginia compiled by workers of the writer’s program of the Work Projects Administration in the State of Virginia.

A note on prayer meetings. Many groups that gathered at these prayer meetings became the congregations of the churches established during Reconstruction. In particular the group that Garland Monroe’s father was part of established the Middle Oak Baptist Church, originally located on the Hardware River, the same river named in the account above. More on the Middle Oak Baptist Church is on the Home page.

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