Archives of Maryland
(Biographical Series)

Henry Hollyday (b. 1771 - d. 1850)
MSA SC 5496-51319
Property Owner, Talbot County


    Henry Hollyday was a Talbot County farmer, and one of the most prominent slave holders on the Eastern Shore. Hollyday was married to the former Ann Carmichael in 1798 and they raised three sons and five daughters together.1,2 His wife's nephew and their future son in law, Richard Bennett Carmichael, was the infamous Civil War era judge who was beaten and imprisoned by Union troops for his outspoken pro-Southern sentiments.3 Henry Hollyday also graduated from Princeton in 1798, then established a law practice in Easton, which would supplement his agricultural holdings.4 As was customary for wealthy slave holders during that period, he was also a political representive of the Shore. Alongside fellow Talbot County planter William R. Hughlett, Hollyday served as a State Senator from 1816 to 1820.5 By 1830, Hollyday had settled into his native community and already held 59 African-Americans in bondage on his Easton area plantation, known as Ratcliffe Manor.6 

    Hollyday never made any public notice of slaves fleeing his property, which was highly unusual for a Shore planter at that time. However, this situation makes more sense considering Henry's high economic standing, and connections within the greater Mid-Atlantic region. Slave holders of his stature were more likely to handle the flight of chattel in a more private manner, employing their own slave catchers while consulting with business and political partners on possible leads. That process was clearly displayed in his correspondance with fellow Eastern Shore aristocrat, Thomas Emory, in 1829. Emory, who would occupy the same Senate position in the late 1820's, was patriarch of the vast Poplar Grove plantation in Queen Anne's County. In the letter, Hollyday informs his associate that, "one of your servants ... stated to my informer that he, and a brother of his, intended to take some convenient opportunity to go off."7

    Their correspondance suggests that there was a network of wealthy whites, who cooperated in order to uncover potential instances of slave flight. Furthermore, Henry Hollyday admits to actively using an "informer," likely one of his own enslaved men. These relationships were further illuminated by an 1834 letter that Robert G. Johnson of Salem, New Jersey sent to Thomas Emory.8 In discussing some local blacks who allegedly stole his sheep, Johnson mentions that one of them may be the property of "my old friend Col.Holliday of Easton." He further suggests that Hollyday come to the trial where he could attempt to identify the "yellow woman ... who will be brought forward as a witness."9 Contrary to popular understanding, living in an essentially "free" state like New Jersey did not preclude one from supporting the efforts of slave holders. In fact, some communities in New Jersey and Pennsylvania were eager to assist southerners like Henry Hollyday because of prejudice against African-Americans living in their midst. It is unclear whether he ever took advantage of Johnson's invitation. However, these connections likely resulted in some success for owners attempting to retrieve their property as, again, planters like Emory and Hollyday never resorted to publishing runaway notices in the paper.

    Henry Hollyday slave holding experience was also unique in that he was not only documented by his own words and those of his peers, but by the very class that he oppressed. William Green was an African-American slave who fled from Talbot County around 1840 and ultimately published his narrative in 1853, when he was living in Springfield, Massachusetts.10 Despite the fact that he was owned by the neighboring Goldsborough family, Green dedicated a chunk of his account to the man he referred to as "Harry Holliday." The former slave's description was far from flattering; in fact, it was almost entirely dedicated to instances of Hollyday's cruelty toward his bondsmen. Green begins by asserting that, "this man's plan was to make one man do the work of two. He half clothed and fed his people."11 His alleged brutality manifested itself through whippings, over work, and exposure to the elements that was considered extreme even by Eastern Shore standards. Green contends that this "cruel miserly man" even caused an old woman to frozen to death after she was forced to search for lost cattle late at night. Barring any legal action, which rarely ever occurred on behalf of enslaved individuals, there would be little documentation to confirm William Green's accusations against Henry Hollyday. However, the fugitive must have felt genuine antipathy toward "this tyrant," since he chose to single him out as representative of the evils of slavery in Talbot County.

    Hollyday's 1849/1850 will stipulated that his land holdings be passed to his sons Richard C., Thomas R., and William M.12 These men are later represented on the 1858 Dilworth Map of Talbot County, just outside of Easton surrounded by several waterways.13 While the slaves were to be dispersed amongst the family members, all of them, a total of 63, were listed in Thomas R. Hollyday's slave schedule in 1850.14 Henry Hollyday died in March of that year, leaving his heirs with approximately $40,000 of taxable real estate.15 The Baltimore Sun remarked only that the former state senator was "well esteemed."16 The Holllyday family continued their prosperity in the area, with little evidence that they freed their slaves or otherwise lost them until the state abolished the institution in late 1864.

Footnotes -

1. James Bordley Jr. The Hollyday and Related Families of the Eastern Shore of Maryland. Baltimore: Maryland Historical Society, 1962.

2. 1830 United States Federal Census, Talbot County, Maryland, p. 29.

3. Bordley.

4. Ibid.

5. Archives of Maryland Historical List, Senate, Eastern Shore (1777-1837)

6. 1830 United States Federal Census, Talbot County, Maryland, p. 29.

7. Poplar Grove Collection, MSA SC 5807, Series 4, pp. 282 - 283, Correspondance regarding possible runaway slaves.

8. Poplar Grove Collection, MSA SC 5807, Series 13, pp. 194 - 197, Correspondance regarding possible runaway slaves.

9. Ibid, p.197.  

10. William Green. Narrative of Events in the Life of William Green, (formerly a slave.) Written by himself. Springfield: L. M. Guernsey, Book, Job & Card Printer, 1853.

11. Ibid, p. 8.

12. TALBOT COUNTY REGISTER OF WILLS(Wills), 1848-1862, JHH 10, pp. 26 - 34.

13. Dilworth, Map of Talbot County, 1858, District 1, Library of Congress, MSA SC 1213-1-456.

14. 1850 United States Federal Census, Slave Schedule, Talbot County, Maryland, Easton District 3, pp. 2 - 3.

15. Will.

16. "Dead". The Baltimore Sun. 9 April, 1850.

Researched and Written by David Armenti, 2012.

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