James Madison, Sr.

James Madison Sr. was born on March 27, 1723, in Orange County, Virginia. His parents were Ambrose Madison, a planter and politician, and Frances Taylor, who was an aunt of Richard Taylor. In 1732, at the age of nine, Madison moved with his family to their new plantation called Mount Pleasant. His father had employed slaves and an overseer to clear the land over five years, establishing cultivation there. In August 1732, Ambrose Madison died after a brief illness, at the age of 36. There was suspicion that he had been poisoned by enslaved individuals; three slaves were charged and convicted by justices of the Commission of Peace, with one slave executed and others returned to their owners after punishment.

Madison was tutored in preparation for his role as a planter and member of Virginia's landowning class. His widowed mother, Frances Taylor Madison, chose not to remarry and remained involved with her family's extensive Taylor connections in the county. James Madison Sr. inherited Mount Pleasant in 1744 upon reaching legal age, which he referred to as Home House. Over time, he expanded his holdings, acquiring additional land to reach a total of approximately 5,000 acres, thus becoming the largest landowner in Orange County. By his death in 1801, he owned 108 slaves.

He married Eleanor Rose "Nelly" Conway on January 9, 1731, in Port Conway, Virginia. Eleanor was also from the planter class; her family’s plantation was named after her. Their marriage produced twelve children:

1. James Madison (March 16, 1751 – June 28, 1836), who became the 4th president of the United States.

2. Francis Madison (June 18, 1753 – April 5, 1800)

3. Ambrose Madison (January 27, 1755 – October 3, 1793); married Mary Willis Lee.

4. Madison's daughter, Mary Madison (February 10, 1758 – March 18, 1758)

5. Eleanor Conway Madison (February 14, 1760 – December 24, 1802)

6. William Madison (May 5, 1762 – July 20, 1843)

7. Sarah Catlett Madison (August 17, 1764 – October 17, 1843)

8. An unnamed son (1766–1766), who died one day after birth

9. Elizabeth Madison (February 6, 1768 – May 17, 1775)

10. An unnamed stillborn son (July 12, 1770)

11. Reuben Madison (September 19, 1771 – June 5, 1775)

12. Frances Taylor Madison (October 4, 1774 – October 4, 1823)

During the American Revolutionary War, Madison served as the chairman of the Orange County Committee of Safety and was commissioned as a colonel in the Virginia militia.