The earliest documentation on John Boswell II is his baptismal record that appears in the Abingdon Parish Register March 5, 1692 in Gloucester, Virginia. He is the son of John Boswell I and Phebe Colegate Iverson Boswell and is the sibling of Joseph, Robert , Mary and Diana.

John grew up on Ware Point and in 1728 married a Ware Point neighbor, Ann Ransom. There is some mystery as to where John spent the next ten years. The existing copies of the early Abingdon Parish Register 1678-1762 do not contain the marriage or birth of their children. St. George's Vestry Book 1726-1745 is only concerned with the acts of the Vestry; it is not a record of the parishioners. The early records of Gloucester Co., and those of Hanover Co., were destroyed. The early Spotsylvania records have been diligently examined. Nowhere has John Boswell II been found until he purchases land in 1740.

In Spotsylvania Co. Deed Book C-151, 30 April 1740, Joseph Brock and his wife, Mary, sell to John Boswell, Planter, for 100 pounds, 980 acres in Spotsylvania Co. This was a part of Larkin Chew's patent of June 4, 1722, repatented by Joseph Brock on 12 September 1738. The deed was recorded 6 May 1740. Larkin Chew patented 15,600 acres in three patents on 4 June 1722. Joseph Brock was Chew's son-in-law and bought land from Chew for resale. The land in the 1722 patents was near the Po and Ta Rivers, about fifteen miles south of Fredericksburg, Virginia.

Our records indicate that John Boswell died of a sudden death and a will book, Spotsylvania Co., Will Book A-321 which bears a date of 10 January 1740 was written. We can only assume that his death occurred after 10 January and before May 5, 1741.

Ann Ransom was the daughter of Peter Ransom and Dorothy Horth, all families who were early settlers on Ware Point in Gloucester. She was born around 1710 and after her marriage to John II in 1728 and after his death, she remained in Spotsylvania County with her six small children. However, the widow Boswell was just over thirty years old and possessed a reasonably attractive estate. About 1742, she married William Gatewood at Spotsylvania County.

The children of John Boswell II and Ann Ransom Boswell are: Ransom (ca 1729-ca1792) Dorothy (ca 1731, John (ca 1733-1802), George (ca 1736-1788), James (ca1737), Frances (ca 1740-pre 1810). The children of William Gatewood and Ann Ransom are: Austin (ca 1743) Ambrose (ca 1745), and William Jr. (ca 1749).