Richard Thomas Haile was mentioned in the 11 December 1760 will of his father John Haile: To Beloved Son Richard Thomas Haile One Negro Man Named Sam, also my Desk...Richard Thomas Haile to be full whole and Sole Executor. The will was proved on 20 April 1761. [Essex County, Virginia, Will Book 11, pages 299–300.]

The sale of the estate of John Haile was held 12 May 1761 “unto Sundry Persons” by Richard Thomas Haile executor. Total valuation £132.1.5-1/2. Recorded 21 November 1763. [Essex County, Virginia, Will Book 12, pages 89–90.]

On 16 November 1767, Richd Thos Haile witnessed a deed from Ambrose Gatewood and Martha his wife of the County of Essex to Thomas Dix of the same. [Essex County, Virginia, Deed Book 30, pages 154–155.]

On 17 June 1771, a division of the remaining estate of John Croxton deceased was recorded. Lots went to John Quarls, Richard Thomas Haile, John Croxton, Richard Jones guardian of the orphans of Samuel Croxton deceased, and Thomas Croxton. Made by J. Edmondson, James Booker, James Banks. [Essex County, Virginia, Will Book 12, page 413.]

On 16 December 1771, Richd Thos Haile witnessed a deed from Thomas Allen and Henry Allen to Thomas Dix. [Essex County, Virginia, Deed Book 30, pages 509–510.]

In his 31 July 1775 will, John Croxton asked that Richard Thomas Haile care for his three children, Carter Croxton, John Croxton and Aris Croxton until they came of age. [Essex County, Virginia, Will Book 13, pages 32–33.]

The will of Richard Thomas Haile was dated 14 November 1787,with a codicil added on 18 September 1789: “In the name of God amen I Richard Thomas Haile of the County of Essex being sick & weake but in perfect mind and memory thanks be to almighty God for the same, I do make this my last will and Testament, that is principally & first of all I Give & bequeath my sould to God that Gave it & my Body to the Earth to be buried in decent manner — I Give demise & Dispose of the same in the following manner & form Item I Lend to my beloved wife Mary Haile all my hold Estate both real & personal During her life — Item I Give to my son John Haile after my Wifes death my Dish & still Item I lend to my son John Haile all my Lands after my wifes death during his natural life and afterwards I Give all my Lands to my Grandson Richard Thomas Haile & my desire is that my son John Haile’s wife should have her dower in the land in case she should be The Longest Liver during her widowhod Item I Leave to my Daughter Joanna Haile choice of my horses & sadle after my wifes death likewise twenty five pounds at the same time Item my desire is that all my Estate that is Lent to my wife Except the Land dish & still to be devided amoung my children whom I Shall name (Vizt) Lewis, [the name Wheeler here crossed out], Benjamin, Joanna, & Richard Haile & that my son [a line of words crossed out here] I Likewise ordain my wife Mary Haile & my son John Haile my hold & sole exors of this my Last Will & Testament revoking & disannulling all other Wills to be void & of none Effect Given under my hand & seal this fourteenth day of November One Thousand seven hundred & Eighty Seven.” Richd Thos Haile [seal]. Witnesses: Thomas Allen, Susannah her + mark Adams, Mary her + mark Croxton. Codicil: “It is my desire the rasing out on the other side shall be so & that Wheeler Haile my son pay to the rest of my children fifty pounds for a negro fellow by the name of Tom who died in his hands & term[?] [words crossed out] likewise in his hands Given under my hand & seal this Eighteenth day of Sept one thousand seven hundred & Eighty Nine.” Richd Thos Haile [seal]. Witnesses: Henry Kidd, Benja Haile, Christopher Ware, James Clark, Richard Haile, Thomas Brooks. Presented in court 20 October 1795 by John Haile, executor, and proved by Thomas Allen and Mary Croxton, and codicil proved by James Clark and Thomas Brooks. [Essex County, Virginia, Will Book 15, pages 193–194.]

According to Beverley Fleet, the original was in the family papers of Judge Francis Wyatt Smith. A legal paper attached to his copy of the will lists Zachariah Crittenden as having married Joanna Haile. [Virginia Colonial Abstracts, Volume II, Beverley Fleet, Baltimore, Genealogical Publishing Co., Inc., 1988, page 347.]

On 18 July 1796, John Haile was granted administration of the estate of Richard Thomas Haile, deceased. John Haile, Thomas Dix, and Ambrose Howerton acknowledge their bound in the penalty of £1,500. [Essex County, Virginia, Will Book 15, page 254.]

Pursuant to an order of Essex County court bearing date 18 July 1796, William Howard, John Minter, and Thomas Roane appraised the estate of Richard Thomas Haile, deceased. Ordered recorded 17 July 1797. Total valuation £1154.4.4.[Essex County, Virginia, Will Book 15, pages 319–321.]

On 17 February 1800, Wheeler Haile was granted administration of the estate of Richard Haile, deceased. Wheeler Haile and John Gibson acknowledge their bond in the penalty of $400. [Essex County, Virginia, Will Book 15, pages 525–526.]

The estate of Richard T. Haile in account with John Haile for the year 1796 was settled on 16 February 1807 by John Jones, John Minter, and Geo. W. Banks, and ordered recorded on 15 June 1807. [Essex County, Virginia, Will Book 17, page 15.]

A sale of the estate of Richard Thomas Haile was made on 1 and 2 February 1808 by John Haile, administrator, and the account of the estate was settled on 3 Febraury 1808, presented by John Haile junr as agent for his father John Haile admr. [Essex County, Virginia, Will Book 17, pages 56–60.]

His relationship to his son John and grandson Richard Thomas Haile are described in a deed in Essex County, Virginia, Deed Book 24, pages 191–197.