Samuel married two wives during his lifetime. Although we know a great deal about Samuel Cupples, little information remains available about his wives. It is interesting to postulate about what kinds of activities these women were engaged in. Women's roles in society were limited in the 19th century and it was a rare woman who made a career or received education beyond high school or finishing school. We do not know the education level of either of the Cupples wives or if they were involved in timely happenings, like the suffrage movement.
The Kells family was well established in St. Louis and, like Samuel Cupples, from Scottish descent. Samuel met his future mother-in-law at the Fourth Street Methodist Church. Elizabeth Kells, a prosperous widow, had three daughters: Harriet, Martha, and Margaret Amelia, the youngest.
Samuel married Margaret Amelia Kells in 1854, but their marriage was a tragically short one. She was plagued by health problems and their only child died in infancy. Margaret Amelia died only four years into to marriage, never living long enough to reside at Cupples House. Apparently, before she died, Amelia asked Samuel to marry her older sister, Martha. This custom was not unusual for wealthy families in this era, because it served as a way of keeping money in the same family. Samuel then married Martha in 1860. They had three children, who all died either in infancy or in early childhood either of cholera or diphtheria, which were both rampant diseases at this time. They adopted their 12-year-old niece Amelia. She was the daughter of Martha's older sister, Harriet Kells Loman, who also had two other daughters, Martha and Mary Belle. This practice, too, was not unusual at the time. Martha Cupples died in 1894, having only enjoyed her new home for only four years.
Like her husband, Martha Cupples involved herself in philanthropic activity. When the Methodist Orphans Children's Home was founded in December 1867, Martha served as one of its directresses. By 1870, she served on the Executive Board of the Home as a Second Vice President, and she was also the Secretary of the Board of Managers. Through the years, Mrs. Cupples also participated in fundraising for the Home. While she devoted most of her energy to the Methodist Orphans Children's Home, the directors of the St. John's Ladies Aid Society named Mrs. Cupples as its first president upon the society's organization in 1876. In 1877, she became involved with the Industrial School and Home for Girls as the Secretary of its Board of Managers for 29 years. Mrs. Cupples was also interested in the Memorial Home for the Aged (Charless Home), the Women's Missionary Society of the Methodist Episcopal Church South, and also the Christian Home for Single Women. Sadly, illness forced Mrs. Cupples to surrender all of her charity work when she succumbed to a mysterious illness that left her bedridden in 1891. She remained paralyzed, unable to leave her room, until her death in 1894.
In 1895, Samuel Cupples provided $100,000 to build the Methodist Orphans' Children's Home in honor of Martha Kells Cupples. He functioned as Treasurer of its Board of Trustees. The Home was later dedicated in May 1896. Mr. Cupples sat on the Men's Board from the time of its inception.