Jack, the person at the center of the controversy, has no biography. He is not even given a last name. We know nothing about him. Was he already DeLancey's slave when DeLancey fled New York? Was Jack born into slavery, or was he abducted from Africa? Did he have family? How old was he? What work did he do for DeLancy, and later for Woodin? Why did he run away from DeLancey? History is silent on the life of Jack, and the only concern the "several gentlemen of the law" have with him is whether or not he is the property of James DeLancey.
DeLancey's 1803 complaint against Woodin describes him as "one Jack a Negro man ...lawfully retained in the service of the said James DeLancey as his slave and servant, to serve him the said James DeLancey, for and during the natural life of the said Jack...". The Negro slave Jack, on May 26, 1800, "...wilfully and without the leave or licence and against the will of the said James DeLancey departed and absented himself from and left the service of the said James DeLancey and went in to the service of the said William Woodin...". Jack himself is not accused of anything other than leaving without permission, nor is he said to have broken any law; property cannot be accused of breaking the law. Jack is nowhere in either document deemed ultimately responsible for his actions; it is William Woodin who is accused of detaining Jack and refusing to return him, not Jack of refusing to return. The very nature of the legal action taken against Woodin shows Jack's relationship to DeLancey; trover is a legal action taken against someone who has found another's lost property and refuses to return it.
William Woodin seems to have seen things differently. Not only did he take in the runaway Jack and employ him for wages, but he also refused DeLancey's demand that his "property" be returned, saying that Jack was not a slave since there was no Law in Nova Scotia to make him one. He continued to resist DeLancey's demands for at least the next three years.
It is quite possible that Jack was DeLancey's slave in New York, where the DeLancey family had its home before the American Revolutionary War forced them to flee to Nova Scotia. He may have been brought to Nova Scotia along with the rest of DeLancey's moveable property in 1783; records show that DeLancey had slaves when he arrived. As valuable property that would be difficult to replace in Nova Scotia, DeLancey would likely have been reluctant to leave Jack behind.
DeLancey certainly thought of Jack as valuable property; in the first judgement in DeLancey vs. Woodin, the judge awarded DeLancey 70 pounds in damages, a significant amount at the time. Three years later DeLancey claimed damages of an astonishing 500 pounds, making Jack very valuable property indeed.
In the end, Jack appears to have won out over DeLancey; after DeLancey died in 1804, Jack was not listed as property in the records of the DeLancey estate.