There is considerable uncertainty about Leonard Henley because several early family history descriptions give similar but conflicting accounts. Much of the problem is the popularity of the name “Leonard”. There were clearly a number of Leonard Henleys and in some cases may have been confused with each other.

One account, written by Mrs. Priscilla M. (Barkley) Godfrey was entitled “HENLEY” and was published in the Virginia Genealogical Society Quarterly in 1969.2167 In this article, Mrs. Godfrey wrote:

Leonard [2], heir to father, 26 October 1694, ‘inherited the original tract, called "Merry Oaks" to which he added a subsequent grant called "Tuckahoe" lying on the James River in James City Co, besides other patents in Henrico Co'. [Mss DAR] Birth given variously as 1684, 1690, 1694, would seem to be incorrect if he imported 4 persons in 1694. But JHS wrote that this Leonard had a son named Leonard Henley.

Leonard [3], born by 1702, who made a deed of land, 17 March 1734, and who was the Leonard who married as below. Leonard served as vestreyman 1730-1750 [JHS], in 1759, according to Blisland Parish records. Leonard died before 17 October 1761, probably 1759. He married 1718, Elizabeth Richardson, "daughter of Robert Richardson of Goochland Co., VA, who owned 'Long Brandon' on the James River, and who sold it to Nathaniel Harrison in 1720", [WBH], "of the same family as former Adjudant General Richardson of Virginia". [Mss DAR] He had three or four daughters [JHS, WBH] and:

Cornelius (or Turner) Henley, b 20 May 1728
Leonard Henley, b 21 Feb 1724
William Henley, b 28 Feb 1732
Richardson Henley, b 1725, d 1781 (tombstone)

The sources she cited (WBH, JHS and Mss DAR) were accounts written in the 19th century and two of them were authored by people who were Henley descendants, albeit several generations removed from the 17th century Leonard Henley. The WBH and JHS referred to as source were Woodford Broaddus Henley and Josiah H. Shinn, whose manuscripts are MSS6 I.H.3895, Mss6 I.H.3895.1, and Mss BW8787a in the Woodward Society in Virginia Historical Society Library files. The Mss DAR was entitled “The Family of Henley,” and was authored by Elizabeth Henley Luce, the daughter of Leonard Henley (son of Cornelius Turner Henley. Mrs. Luce was therefore the great granddaughter of the 17th century Leonard Henley.

With regard to the sources relied on by Mrs. Luce, Woodford Broaddus Henley (1834-1909) was the son of Richardson Henley and Mary Ann Taliaferro.

Thus, Mrs. Luce believed that there were two Leonard Henleys, one born early enough that he could receive a patent for land in 1694 for four persons he had imported sometime prior to this date. She referred to this man as Leonard [2], the number indicating the generation in America. She thought that Leonard [2] had a son Leonard [3], who married Elizabeth Richardson and had the four sons listed above.

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On the other hand an 1896 article in the William and Mary College Quarterly asserted that there was only one Leonard between Reynolds Henley and the four sons listed above:2168

Leonard Henley was descended from Reynold or Reginald Henley, who settled in James City county as early as 1661-See Land Patent Book 8, fol. 397 issued Oct. 26, 1694 to Leonard Henley for 360 acres in James City - "175 acres thereof, as heir to his father, REYNOLD HENLEY decd, to whom it was sold & assigned 15th Dec. 1661, by Thos. Holliday." - This Leonard m. Miss Richardson, by whom he had 4 sons, 1, Major Richardson Henley* of "Merry Oaks," James City; 2, Leonard Henley of Henrico; 3, Turner Henley of James City, father of Leonard, who m. Eliz Dandridge, and 4, William Henley whose descendants settled in Amherst.

*Ancestor of Judge Richardson Leonard Henley, of Williamsburg, VA.

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The following essay on Philemon Woodward2169 also mentions the Henley family, naming a daughter (Rebecca), giving 1690 as Leonard’s birth year, but a death year 10 years earlier than the date his will was probated:

“Philemon Woodward married Rebecca Henley, whose birth is given as June 2nd, 1735. Leonard Henley, her father, was born in 1690 and lived at "Merry Oaks," until his death in 1752. He was a life long neighbor and, over many years, a fellow vestryman of Lancelot Woodward. His wife was Elizabeth Richardson, daughter of Robert Richardson, owner of "Lower Brandon," on the James River, until he moved, in 1720, to Goochland County. Leonard Henley had eight children, four sons and four daughters, the youngest child being Rebecca. He was the only son of Reginald Henley, the immigrant, who, in 1661, patented 360 acres in Wilmington Parish, James City County. "Merry Oaks," his seat, was conveyed by deed to his four year old son- Leonard, in 1694. Leonard Henley succeeds George Woodward, in 1739, on the latter's retirement from the vestry; he, then, becomes Churchwarden and is succeeded, as such, by Lancelot Woodward, two years later. They remain together on the vestry, until Lancelot's death, whom he survives by a couple of years only. What more natural than that the youngest daughter of Leonard Henley should wed a younger son of Lancelot Woodward?”

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Other Henley family trees list two additional sons for Reynolds Henley and also ascribe several daughters to Leonard Henley, in addition to the four sons listed by Mrs. Godfrey: Martha (m William Drummond), Margaret (m John Randolph), Mary Elizabeth (m William Hamner), Rebecca (m Philemon Woodward), Henrietta (m Richard Henderson) and Anne (m Richard Bullock).2170 However, one of these alleged daughters, Mary Elizabeth Henley (m William Hamner) is reported elsewhere to have been the daughter of Leonard Henley Jr.2171 There is a problem with this assignment, as Leonard Henley Jr. is said to have been born 1724 and Mary Elizabeth Henley is said to have been born 1731.

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Another treatise on the Henley family was published privately by Ernest E. Carrick in July 2006.2172 Mr. Carrick favors Elizabeth Keeling, 2nd wife of Reynolds Henley, as mother of Leonard Henley, rather than Susan Turner. For Leonard Henley he gives a birth year of 1656 and a death year of 1715 and says that Leonard married Mary Elizabeth Richardson in 1708. Mr. Carrick lists one of the children of this Leonard Henley as another Leonard Henley, b 1695 d 1748, whose wife was Susan Turner. This seems problematic in light of the 1708 marriage date he gives for Leonard Henley I and Mary Elizabeth Richardson. This assignment of Susan Turner as wife of Leonard Henley, rather than his mother, is at odds with most accounts. Because of these rather radical departures from other accounts, I do not take this genealogy very seriously.

On 17 March 1734 Richard Wade of Goochland Co, planter, conveyed to Leonard Henley of Blissland Parish, James City Co, for one year, for 5 shillings sterling, 202 acres on Little Tuckahoe Creek and lying in both Goochland and Henrico counties. The boundaries were in a flat valley near the head of Little Drinkinghole Creek, a small branch on the west side of Little Tuckahoe Creek in Goochland Co, next to Thomas Hardin, on the north side of the same branch in Henrico Co and on the west side of Little Tuckahoe Creek in Goochland Co. On the following day a subsequent deed for the same purpose involved another payment of 10 pounds, 10 shillings. (Deed Book 2, pages 65-66.)

Leonard's will was written September 10, 1759, proved October 19, 1761 in Blissland Parish, New Kent, VA.

From the Virginia Genealogical Society Quarterly, 1969, Vol. 7, No. 2, pp. 38-42:

“HENLEY”
Compiled by Priscilla M. (Barkley) Godfrey (Mrs. Thomas E. Godfrey)
Petersburg, Virginia 23803

Hezekiah Henley, given without proof as forebear in England.

Reynold [1] (Reginald) Henley settled in James City County, VA, as early as 1660 [Family letters]. Land Office Book 8, fo. 397, reel 8, Virginia State Library describes a tract of land containing 360 acres bounded from Cattail Meadow--on a neck of land lying on northside Merryman's Swamp, 175 acres thereof due to Leonard [2] Henley as heir to his father, Reynold Henley, deceased, to whom it was sold and assigned 15 Dec 1661, by Thomas Holliway 185 acres residue thereof is further due for importation of 4 persons by Leonard. Reynold [1] Henley married Susan, daughter of Cornelius Turner.

“The immigrant had three sons, Phillip [2] who settled in Gloucester Co., living in 1665 on Eastermost River, evidently dying without issue and who was the guardian of Leonard [2]. Robert [2] settled in Essex Co, and married a Gates. He is said to have left no male issue. His will, proved 1685, mentions no children. However, one of his granddaughters in the last century (1700s) adopted the eldest son of a representative of the James City branch who was brought up and married in Essex but settled in King & Queen Co leaving a large family there and thereabouts.” [Mss DAR]

Leonard [2], heir to father, 26 October 1694, ‘inherited the original tract, called "Merry Oaks" to which he added a subsequent grant called "Tuckahoe" lying on the James River in James City Co, besides other patents in Henrico Co'. [Mss DAR] Birth given variously as 1684, 1690, 1694, would seem to be incorrect if he imported 4 persons in 1694. But JHS wrote that this Leonard had a son.

Leonard [3], born by 1702, who made a deed of land, 17 March 1734, and who was the Leonard who married as below. Leonard served as vestreyman 1730-1750 [JHS], in 1759, according to Blisland Parish records. Leonard died before 17 October 1761, probably 1759. He married 1718, Elizabeth Richardson, "daughter of Robert Richardson of Goochland Co., VA, who owned 'Long Brandon' on the James River, and who sold it to Nathaniel Harrison in 1720", [WBH], "of the same family as former Adjudant General Richardson of Virginia". [Mss DAR] He had three or four daughters [JHS, WBH] and -

Note: The WBH and JHS referred to as source were Woodford Broaddus Henley and Josiah H. Shinn, whose manuscripts are MSS6 I.H.3895, Mss6 I.H.3895.1, and Mss BW8787a in the Woodward Society in Virginia Historical Society Library files.