He was born free, but enticed into helping to drive horses to Virginia, a slave state, and was sold into slavery in early 1851.
It seemed to be settled with the Francis Jackson vs. John W. Deshazer case when he was ruled to be free in 1855, but he was held as a slave until 1858.
Jackson lived a continual cycle of being sold to new slaveholders, running away, getting caught, and then being returned to his latest owner.
An attorney, George Cameron Mendenhall, visited him in jail in North Carolina after he ran away from a nearby plantation.
Believing Jackson's chain of events, Mendenhall filed legal proceedings that ultimately freed him in August 1858.
During the time that he was enslaved, abolitionists from Pennsylvania tried to track him down and provide legal evidence and depositions that he was free.
[5][6] He was raised by a farmer and an "ardent abolitionist", John Young, of Indian Run,[5][7] north of New Castle.
William Stewart of Mercer County and Judge John Reynolds of New Castle attempted to bring Jackson back to Pennsylvania by providing proof that he was free.
[5][13] In 1851 and 1852, the Free Presbyterian and The Anti-Slavery Bugle newspapers tracked his case and published information about his whereabouts.
[3] After Jackson was arrested in Botetourt County, he filed his first lawsuit against Scott, stating that he was illegally enslaved.
Glass, an attorney from the city, sought and received proof that he was a free man from New Castle and Mercer County, Pennsylvania.
[6] A witness from Virginia stated that Jackson had said he was previously enslaved by May's father and belonged to another slaveholder when he was sold to Scott.
[2] The case went to trial in October 1853 with depositions by three people who knew the Jacksons in Pennsylvania and stated that they were free.
[2][g] Since he was kidnapped, Jackson learned that the justice and legal system worked efficiently for slaveholders, and people who were wrongly enslaved had a very hard time being heard and proven free.
Noting that "he is prosecuting a suit for his freedom in the county of Botetourt in this state," the petitioner "prays your Honor to award an Injunction to [restrain] the said John W. Deshazor from conveying him away and to require the said Deshazor to give bond and security for the forthcoming of your Orator to await the determination of the suit aforesaid.
[5][21] After it was determined how to find Jackson, people in Pennsylvania planned for his release and started a fund for expenses.
Having learned that North Carolina's governor agreed to Jackson's release, George C. Morgan traveled south.
[7] In the meantime, Jackson was in jail, having run away from Frederick W. Swann's plantation in Moore County, North Carolina.