In March 1847, he married Martha Martin, the 21-year-old daughter of wealthy Colonel Robert Martin of North Carolina.
The year after their marriage, Martha's father died and bequeathed her a 2,500-acre cotton plantation with 100 slaves on the Pearl River in Lawrence County, Mississippi.
He appointed Douglas the property manager but, as a senator of the free state of Illinois, and with presidential aspirations, Douglas found the Southern plantation presented difficulties.
He created distance by hiring a manager to operate the plantation, while using his allocated 20 percent of the income to advance his political career.
His sole lengthy visit to Mississippi was in 1848, and he made only brief emergency trips thereafter.

The newlyweds moved their Illinois home from Springfield to fast-growing Chicago in the summer of 1847.
They had two sons: Robert M. Douglas (1849–1917) and Stephen Arnold Douglas, Jr., (1850–1908).
Martha Douglas died on January 19, 1853, after the birth of her third child, a daughter.
The girl died a few weeks later, and Douglas and the two boys were bereft.

On November 20, 1856, Douglas married a second time, to 20-year-old Adele Cutts, a southern woman from Washington, D.C, She was the daughter of James Madison Cutts, a nephew of former President James Madison, and Ellen O'Neal, a niece of Rose O'Neal Greenhow.
Her mother was from a Maryland Catholic family and raised Adele as a Catholic.
With Stephen's approval, she had his two sons baptized as Catholic and reared in that faith.
She had a miscarriage in 1858 and became ill.
The following year, Adele gave birth to a daughter, Ellen, who lived only a few weeks.
In March 1847, he married Martha Martin, the 21-year-old daughter of wealthy Colonel Robert Martin of North Carolina. The year after their marriage, Martha's father died and bequeathed her a 2,500-acre cotton plantation with 100 slaves on the Pearl River in Lawrence County, Mississippi. He appointed Douglas the property manager but, as a senator of the free state of Illinois, and with presidential aspirations, Douglas found the Southern plantation presented difficulties. He created distance by hiring a manager to operate the plantation, while using his allocated 20 percent of the income to advance his political career. His sole lengthy visit to Mississippi was in 1848, and he made only brief emergency trips thereafter.
The newlyweds moved their Illinois home from Springfield to fast-growing Chicago in the summer of 1847. They had two sons: Robert M. Douglas (1849–1917) and Stephen Arnold Douglas, Jr., (1850–1908). Martha Douglas died on January 19, 1853, after the birth of her third child, a daughter. The girl died a few weeks later, and Douglas and the two boys were bereft.
On November 20, 1856, Douglas married a second time, to 20-year-old Adele Cutts, a southern woman from Washington, D.C, She was the daughter of James Madison Cutts, a nephew of former President James Madison, and Ellen O'Neal, a niece of Rose O'Neal Greenhow. Her mother was from a Maryland Catholic family and raised Adele as a Catholic. With Stephen's approval, she had his two sons baptized as Catholic and reared in that faith. She had a miscarriage in 1858 and became ill. The following year, Adele gave birth to a daughter, Ellen, who lived only a few weeks.
Stephen A. Douglas