Richard Thomas Haile is mentioned in the will of his grandfather, Thomas Dix, in 1784.

Richard Thomas Haile is mentioned in the will of his grandfather, Richard Thomas Haile, in 1787. Richard, the grandfather, willed that his lands were to go to his son John during John’s life, and that after John’s death they were to go to Richard, the grandson. [Essex County, Virginia, Will Book 15, pages 193–194.]

In obediance to an Order of Essex Court dated January 21st 1799. We the subscribers have devided the Negroes Racel and Increase between Elizabeth Hundley and Richard Thomas Haile, Tunstal, Isaac, and Ellen have falled to Elizabeth Hundley at £117:10:0 Rachel and two Children Joe and Alic to Richard Thomas Haile at £115. 29th January 1799
By James Wright, Carter Croxton, John Minter, and James Allen
At a Court held for Essex County at Tappa. the 18th day of February 1799 — This report of the Devision of Slaves between Elizabeth Hundley who was Elizabeth Hail & Richard Thos. Haile, which was devised to them by TDix decd. was this day returned and ordered to be recorded.
[Essex County, Virginia, Will Book 15, page 441.]

John Haile and Richard Thomas Haile, an infant by John Haile his next friend, brought suit against Jno Stodghall and Wheeler Haile in 1800. Depositions in the case were made at the house of Mary Haile, the widow of Richard Thomas Haile. The bill alleged that Wheeler Haile had illegally sold land and had been disowned. [Essex County, Virginia, Box Chancery No. 11, Items 11-D-62, 11-D-68, 11-D-73, 11-D-76.]

On 20 October 1800, Richard Thomas Haile, along with Jno Haile, Charles Howerton, Ambrose Hunley, William Newbill, George Howerton and Wm Howerton bound themselves $4,000 to Essex County court, as Jno Haile and Charles Howerton were named administrators of the goods of Ambrose Howerton deceased. [Essex County, Virginia, Will Book 16, pages 37–38.]

On 5 July 1801, Essex County Court send a request to King and Queen County Court for the appearance of Wheeler Haile, stating that John Haile and Richard Thomas Haile had won a decision against Wheeler Haile and John Stoghill but had received no satisfaction. [Essex County, Virginia, Box Chancery No. 22, item 22-G-13.]

On 22 July 1807, an indenture was made between Richard T. Haile and Judith Todd his wife of the first part, Lewis Dix of the second part, and Ambrose Hunley of the third part. In a deed dated 22 November 1805, Richard T. Haile and Judith T. his wife did convey in trust to Lewis Dix real estate and personal property, provided that Dix would support the Hailes during their lives. After the death of Richard and Judith, Dix was to convey to their children all the property. Included in the property conveyed was a tract of land “devised by Richd T. Haile, decd to Mary Haile his widow, during her life with remainder to John Haile, the son of the said testator & father of Richd T. Haile the party hereto…” The reason for the trust was the Richard T. Haile and Judith his wife were in debt, and Dix was to pay off their creditors while managing the property. A list of the creditors is included in the deed of 22 July 1807. It is now “found to be most conducive to the interest of the said Haile & his wife & their children to sell the said land, or [illegible] aforementioned devised by the said Richd T. Haile, the grandfather as aforementioned to raise money to pay the said debts, & to provide an equivalent to Richard T. Haile, the son of the said Richd T. Haile & wife parties hereto out of a part of the other estate conveyed to the said Dix…” Therefore Richard and Judith Haile and Lewis Dix sell for 400 pounds 10 shillings the land to Ambrose Hunley. This is land on the north side of Piscataway Swamp. Signed R: T: Haile, Judith T. Haile, Lewis Dix. Witnesses: Robt Hill, Wm S--ther, Joseph Hester, Wm his x mark Schools. Recorded 15 October 1807. [Essex County, Virginia, Deed Book 37, pages 273–276.]

In another deed of the same date, details of the deed immediately above are reiterated. “The said Richard T. Haile & Judith his wife had previously conveyed to the said Lewis Dix that tract of land whereon the said Richard T. Haile did then reside (including the land purchased or bargianed for by James Noel decd in his life time from Mr Latane Esqr) & described to be the land whereon James Noel decd, the father of the said Judith formerly lived situated in the parish of St Ann & County of Essex & containing by estimation 1100 acres…” [Essex County, Virginia, Deed Book 37, pages 278–281.]

Richard Thomas Haile received a slave named Abraham through the last will and testament of his father John Haile, dated 3 March 1809 and proved 17 September 1810. [Essex County, Virginia, Will Book 17, pages 210–211.]

The estate of Elizabeth Hawes in account with Ro. Hill from 1813 to 1816 was settled by R T Haile, J H Noel, and John Keesee, recorded 15 July 1816. [Essex County, Virginia, Will Book 18, pages 305–306.]

He is mentioned as deceased in the 1827 will of Catharine Dix, his aunt.

On 4 October 1836 a deed was made between Richard T. Haile, Elzer Fogg and Eliza T. his wife, Joseph M. Armstrong and Susan A. his wife, Maria D. Haile, James N. Haile, John S. Haile, Robert L. Haile and Bernard H. Haile, the said Richard T., Eliza F. Susan A., Maria D., James N., John S., Robert L. and Bernard H. being children of Richard T. Haile late of Essex County of the first part, and Ambrose Hundley, Richard T. Hundley, Susanna Mann, Sarah Pendleton the wife of Joseph H. Pendleton, Emaline, Louisa, William, Hugh, and Peter Campbell, children of Mary Campbell deceased, and Mary and Thomas Wood, children of Nancy Wood, deceased, and grandchildren of the said Ambrose Hundley decased of the second part. On 22 November 1805, Richard T. Haile and Judith T. his wife, the parents of the parties of the first part, had sold in trust during their lifetimes to Lewis Dix real and personal property that had been willed to Richard T. Haile by his grandfather, the land having been in trust to his grandmother Mary during her lifetime, with remainer to their son John Haile, the father of the Richard T. Haile who sold the property to Lewis Dix. There was another indenture made between Richard T. Haile and Judith T. his wife of the first part, Tandy Dix of the second part, and Ambrose Hundley of the third part, in which Ambrose Hundley paid unto the parties of the first and second part 400 pounds 10 shillings for 534 acres, it being the same land as in the first deed. Another indenture, dated 22 July 1807 and made between the same parties as in the second deed conveyed a sufficiency to Ambrose Hundley to guarantee the second deed, with conditions such that their son Richard T. Haile should receive an equivalent for his or their interest in the said land. Ambrose Hundley has since died intestate. Elizabeth Hundley received some of the land as her dower, and the residue was allotted to Ambrose Hundley, Richard T. Hundley, and John Hundley deceased, his children. In the meantime, Richard T. Hundley had purchased 68 acres of the land from his brother Ambrose in 1829. Richard T. Hundley also purchased 90 acres owned by his deceased brother John at a court ordered sale, and he then conveyed this land to Susan Mann, Joseph H. Pendleton and Sarah his wife, and Warner Lewis acting as commissioner. In this present indenture, the parties of the first part for $5 quit claim to the land. Dated 4 October 1836. Signed Richd. T Haile, E T Fogg, Joseph N Armstrong, S. A Armstrong, M. D. Haile, James N Haile, John S Haile and Robert L Haile. Witnesses: Geo Wright, Edward Wright, James Munday. Recorded 11 October 1836. [Essex County, Virginia, Deed Book 45, pages 191–197.]