Caleb Jones was a planter, a slave owner, and sheriff of Somerset County, Maryland. In 1776, the Maryland council of safety required him to post bond for his good behavior and obedience to the Continental Congress and Convention. However, Jones joined the Maryland Loyalists during the American Revolutionary War and served as a captain after fleeing to New York City.

In 1783, Jones obtained a grant on the Nashwaaksis Stream near St. Anne’s Point. He briefly returned to Maryland, leaving behind two slaves he had purchased in New York City, and returned with seven more to New Brunswick. However, upon his return, he found that the slaves working on his land had escaped.

In 1800, Caleb Jones became involved in a case to test the legality of slavery in New Brunswick when a woman named Nancy, whom Jones was detaining as a slave, claimed her freedom. The case was presented to the Supreme Court, and the judges were divided on the issue of slavery. Chief Justice Ludlow and Joshua Upham declared slavery legal, while Isaac Allan and John Saunders declared it illegal. Since the bench was equally divided, no judgement was recorded, and the slave was returned to her master. However, as a result of Judge Allan’s decision, he released his slaves, and several other slave owners followed his example.

Caleb Jones was dissatisfied with his life in New Brunswick and felt that he had not been adequately compensated for his losses during the war. He became involved in disputes with the government, and portions of his land were escheated due to non-fulfillment of grant conditions. In 1802, Jones unsuccessfully attempted to win a seat in the House of Assembly. He was accused of making seditious remarks by seven York County magistrates, including Dugald Campbell and Stair Agnew, who requested that he be removed from his position as magistrate. However, there is no record of the cancellation of his commission. Jones continued to criticize the government and was involved in disputes over land and ownership of slaves until his death in 1816.

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