[1][2] The only son to survive childhood of Daniel Parke Custis, a wealthy planter with nearly three hundred slaves and thousands of acres of land in five Virginia counties, and the former Martha Dandridge, he was most likely born at White House, his parents' plantation on the Pamunkey River in New Kent County, Virginia.

The Washingtons raised Jacky and his younger sister Martha "Patsy" Parke Custis (1756–1773) at Mount Vernon.

[3][1] His stepfather was not overly fond of Custis, and considered the child troubled, lazy and "free-willed" for taking no interest in his studies.

[3][1] Martha Washington had supervised the boy's earliest education, but by 1761 the family hired Scotsman Walter Magowan as a private tutor.

[2] In May 1773 Custis began to attend King's College (later Columbia University) in New York City, but left soon after his sister died.

Its restored mansion is the center of Rosaryville State Park in Prince George's County, Maryland.

After their marriage, the couple settled at his father's White House plantation in rural New Kent County.

[1] However, one account claimed Custis served on Washington's staff during the Siege of Boston in 1775–1776 and as an emissary to the British forces there.

[1] En route to Yorktown he also made inquiries about 17 slaves who had reportedly fled to British lines.

[1][19][20] Although Custis had become well-established at Abingdon, his financial affairs were in disarray because of his poor business judgement as well as wartime conditions.