Anthony Johnson was one of the first slaves brought to English North America in the year 1621. Although he was a slave for life, he was able to purchase his freedom. He prospered in freedom and bought a slave named John Casor.
Johnson's white neighbor encouraged Casor to run away in the year 1655 when Casor had a disagreement with Johnson. When captured, Casor claimed that he was an indentured servant and had already served his years, the court disagreed and made Casor a slave again to the black Johnson.
Moreover, the court fined Johnson's white neighbor, Robert Barker, for encouraging the enslaved Casor to run away to freedom and made him pay for Johnson's court fees.
https://edu.lva.virginia.gov/dbva/items/show/126