Born on the island of Jamaica, where two previous generations of De Leons lie buried, Jacob made his way to America at a young age. Very likely he arrived during the Revolution and he may have fought, although family legend that attributed to him a captaincy under DeKalb seems apocryphal.

His first location was New York, where he must have early established himself within the city’s Jewish elite. In 1789 he married Hannah Hendricks, daughter of Uriah and Eve Esther Gomez Hendricks, and sister of the celebrated Harmon Hendricks. The following year their first son, Abraham, was born. He was named for De Leon’s father who had died a few years earlier in Spanish Town.

By 1796 the family—now including three more children—had moved to Charleston. There, De Leon again rose through the ranks of the Sephardic mercantile class. De Leon involved himself extensively in freemasonry, and was followed in this by his sons. Indeed, his eldest, Worshipful Master of Camden’s Kershaw Masonic Lounge Lodge No. 29 Abraham De Leon would help welcome Marquis the de Lafayette on his visit to South Carolina, and so impressed was the marquis with De Leon’s French, that he presented him with his own grand master’s jewel.

South Carolina was to prove the De Leon home for a number of generations. Jacob died in Columbia and Hannah in Camden. Ten of his eleven male descendants would serve in the Confederacy, eight losing their lives in battle.