Jockton was first enslaved by Ebenezer Hinsdale of Deerfield, Massachusetts, and Hinsdale, New Hampshire. He was one of three men enslaved by Hinsdale and all lived in his Deerfield home.
After Ebenezer's death, his wife, Abigail took Jockton with her when she married Col. Benjamin Hall of Cheshire, Connecticut, and again when she married her third husband, Judge Ebenezer Silliman of Fairfield, Connecticut. He died in 1775, and after Tories burned their home in 1779, Abigail returned to Deerfield, probably bringing Jockton with her. In her 1785 will, Abigail left her land to her heirs and the proceeds from the sale of it to Jockton:
one hundred acres of Land which I have in Westmoreland in the County of Cheshire & State of New Hampshire being all the Land which I now own there for the Executing & perfect finishing whereof I do by these present give grant will & transfer to my Executors hereinafter named or wither of them & their respective Executor or Executors full power and authority to grant bargain sell convey and assure the said one hundred acres of Land to any person or Persons and their Heirs forever in Fee Simple by all and every such Lawful ways and means in the Law as to my said Executors or either of them as to their respective Executors shall seem fit or necessary and the Proceeds of Such Sale I give to Jocktan a Molatto formerly Servant of my said Husband Ebenezer Hindsdale provided said Jocktan shall within four years after my decease be a subject of either of the United States of
America and Claim the Legacy aforesaid...