In March 1784, John Haile signed a petition for the building of a road. [Essex County, Virginia, Box Chancery No. 2, item 2-H-10.]

The estate of Henry Allen in was account with Philemon Gatewood from 1783 to 1785. Settled to 18 November 1785 by Thomas Dix, John Haile and Thomas Dix Junier on 18 January 1786. Ordered recorded 19 June 1786. [Essex County, Virginia, Will Book 14, pages 16–22.]

On 18 January 1787, a division of the Negroes of Henry Allen was made by a Tho: Allen, James Sullivan and John Haile. Ordered recorded 21 January 1787. [Essex County, Virginia, Will Book 14, pages 92–93.]

John Haile is mentioned in his father Richard Thomas Haile’s will of 1787. John was to have all of his father’s lands during his life, and they were then to pass to Richard Thomas Haile, with dower rights to John Haile’s wife. John was named an executor and presented the will in court on 20 October 1795. On 18 July 1796 he relinquished the executorship and obtained a certificate of administration. [Essex County, Virginia, Will Book 15, pages 193–194.]

On 15 June 1789 an inventory of the estate of Thomas Dix Senr was recorded, made by Ambrose Greenhill, John Haile and James Wright. [Essex County, Virginia, Will Book 14, pages 150–152.]

On 26 September 1794, Ambrose Greenhill, Thomas Dix and John Haile settled the estate of Henry Allen was in account with Philemon Gatewood. Ordered recorded 21 April 1795. [Essex County, Virginia, Will Book 15, pages 146–150.]

On 18 July 1796, “John Haile the nominal executor in the within will of Richard Thomas Haile decd. came into Court, and relinquished his right of executorship to the same. And on his motion, certificate was granted him for obtaining administration on the estate of the said decd with his Will annexed, he having made oath and entered into Bond with security according to law, which Bond was ordered to be recorded.” [Essex County, Virginia, Will Book 15, page 94.]

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.]

The estate of Richard T. Haile in account with John Haile for the year 1796 is found in Essex County, Virginia, Will Book 17, page 15.

The estate of Rice Fawcett in account with John Minter for 1796 was settled on 10 October 1796 by Thos Dix, Jno Haile and Jas Wright. Ordered recorded on 17 October 1796. [Essex County, Virginia, Will Book 15, pages 264–265.]

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 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 11 July 1804, a division of the estate of Richard Haile was made by Thos Wright, John Minter, and Carter Croxton, also including a settlement of the administration of the estate by Wheeler Haile and an account of the estate sale made on 19 September 1801. The estate was divided equally between Mary Haile, John Haile the representative of Lewis Haile, Wheeler Haile, Benjamin Haile, Zachariah Crittenden who married Joanna Haile. [Essex County, Virginia, Will Book 16, pages 298–299.]

In 1830, orators and oratrices John St. John and Betty his wife, and Harry Howerton, Rachel Howerton, Patsey Gaines Howerton and Robert G. Howerton infants by John St. John complained to the Chancery Court. That Ambrose Howerton died ____ seized of 200 acres of land in Southfarnham Parish and the County of Essex and slaves and other property, leaving Cathe Howerton his widow and your orators and oratrices Betty W. St. John and Harry, Rachel, Patsey Gaines and Robert G. Howerton his only children. Administration of the estate was granted to Charles Howerton and John Haile. [This suit also includes other papers and maps.] [Essex County, Virginia, Box Chancery No. 28, item 28-O-21.]

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.]

On 3 February 1808, a division of the slaves of the estate of Lewis Haile was made by John Jones, Thos. Wright, and Reuben M. Garnett. Lots went to Zachariah Crittenden, Wheeler Haile, John Haile, and Ben: Haile. The division states that both Lewis and Richard Haile died intestate without issue. [Essex County, Virginia, Will Book 17, pages 332–333.]

The will of John Haile was dated 3 March 1809: “In the name of God Amen, I John Haile Senr of Essex County and State of Virginia, being in my sound and perfect senses, thanks be to God for the same, do think proper to make this my last will and Testament, hereby revoking and disannuling all former Wills by me heretofore made — Imprimis I recommend my soul to the supreme being, Trusting that my sins committed here may be forgiven, and my body to the earth to be descently entered at the descretion of my executor hereafter named — Item I Give and bequeath to my son Richard Thomas Haile, a Negro man named Abraham, to him my said son and his heirs forever, the said Abraham having fallen to me by the division of my father’s estate — Item, I give & bequeath to my daughter Elizabeth Hunley a negroe girl named Maria, to her my said daughter and to her heirs forever, the said girl named Maria having also fallen to me by the division of my said Fathers estate — Item — Should either my my aforesaid children die without Heir lawfully begotten of their bodies, then and in that case, I give the two Negroes, and the increase of the girl Maria, to my son John Haile junior, and his Heirs forever — Item, I Give and bequeath to my son John Haile jr, all the property which I may die possessed of, except the two negroes befor [sic] bequeatted to him my said son, John, and his heirs forever, to include both real and personal — Lastly I nominate and appoint my son John Haile jr executor to this my last will and Testament, In Testimony whereof I have hereunto subscribed my name and affixed my seal this 3 day of March 1809”. Signed Jno Haile sr. Witnesses: Gabriel Purkins senr, Leond Burnett. Will proved 17 September 1810; John Haile junior relinquished executorship and was named administrator. Administrative bond for $12,000 follows. [Essex County, Virginia, Will Book 17, pages 210–212.]

On 17 September 1810, John Haile, Robert G Haile and Laurence Muse were bound in the penalty of $12,000 for John Haile’s administration with the will annexed of the estate of John Haile Senr. [Essex County, Virginia, Will Book 17, pages 211–212.]

On 15 September 1828, Robert G. Haile and Anthony S. Barnes were bound in the penalty of $6,000 for Robert G. Haile’s administration de bonis non of the estate of John Haile, deceased. [Essex County, Virginia, Will Book 21, page 285.]

The estate of John Haile, deceased, in account with Robert G. Haile, administrator, from 1829 to 1831 was ordered recorded 20 June 1831. Mentions payment of tax on land in Frederick County. [Essex County, Virginia, Will Book 22, pages 296–300.]

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