Richard Thomas Walker Duke, son of Richard and Maria Walker Duke, was born 6 June 1822 in Charlottesville, Virginia, where he spent his childhood. After attending private schools, he entered Virginia Military Institute and finished second in the class of 1845. Upon graduating he taught school in Lewisburg, Virginia (now West Virginia), but returned to Charlottesville when his father died in 1849, and began studying law at the University. In 1850, he started his own law practice, and over the next ten years built a law office, was chosen one of Charlottesville's first aldermen, served briefly as mayor, and became commonwealth's attorney. He married Elizabeth Scott Eskridge of Staunton, and they had two sons, William and R. T. W. Jr. (Tom), and a daughter, Mary, all of whom lived to adulthood; two other children died in childhood.

As colonel of the 48th Regiment of the Virginia Volunteers, R. T. W. Duke took an active role in the Civil War. In 1864, he resigned his commission because of a dispute with a superior officer, but re-enlisted thirty days later. He surrendered with his troops at Silas Creek in 1865, and returned to his law practice and position as commonwealth's attorney. From that time on, Duke was known as "the Colonel," and in honor of his service in the recent war, the local camp for the Sons of Confederate Veterans was named for him.

In 1863 Duke bought Sunnyside, a 70-acre tract of land northeast of Charlottesville (on which the Law School is now located), and farmed this property until his death. He was chosen secretary/treasurer of the board of trustees of the Samuel Miller Fund, established in 1869. In 1870, Duke assumed the fifth district's Congressional seat for two terms as a member of the Conservative party. Lobbying for a strong South throughout his term, Duke actively opposed the 14th Amendment. R. T. W. Duke died after a lingering illness in the summer of 1898.

William R. Duke, born in 1849, possessed his father's farming instincts and commitment to political involvement. Together they farmed and resided at Sunnyside, whose ownership William shared with his brother Tom after their father's death. Although William studied law at Virginia, and in 1883 joined his father's law practice, he devoted more energy to farming and such groups as the Virginia Cattlemen's Association. In 1897 he was elected delegate to the Virginia General Assembly. Like his father, William was also involved in local affairs, serving, for example, as clerk of the Miller Fund board of trustees for many years. William died in 1929 and was survived by his sons, William (Billy) and Camman.

Since he was born in 1853, Richard Thomas Walker Duke Jr. (Tom) witnessed the Civil War during his impressionable boyhood years and later wrote about those experiences. A gifted writer and student of languages, Tom studied classics, French, German, and English literature when he entered the University of Virginia in 1870. He was awarded the Thomas Jefferson Prize for the best essay in 1872, and then turned his attention to the study of law in 1873-74. It is likely that he later read law for a time in his father's office before passing the bar. Although the practice of law became his career, Duke wrote prose and poetry the rest of his life, and was published in the New York Herald and such magazines as Century, Lippincott's, and Illustrated American.

Throughout his long career, Tom was active in town, University, and state affairs. Among the organizations in which he held office were the Masons, Zeta Psi fraternity, the Sons of the American Revolution, the Sons of Confederate Veterans, the Miller Board, the UVA Alumni Association, and the state Democratic Committee. He served from 1886 to 1901 as judge of the Corporation Court (now called the Circuit Court), as commonwealth's attorney from 1916 to 1920, and as a member of the Committee to Revise the Virginia Code in 1908. In addition, he sat on the boards of a variety of corporations, including the Charlottesville Ice Company, the First National Bank, and a number of Kentucky and West Virginia coal development companies in which his family had invested. From 1907 to 1910, Tom edited the Virginia Law Journal.

Tom Duke married Edith Ridgeway Slaughter in 1884, and they produced six children, of whom five grew to maturity: Mary, R. T. W. III (Walker), John Flavel Slaughter (Jack), William Eskridge, and Helen Risdon. He built a spacious home for his family at 616 Park Street. A frequent traveller because of his practice, Duke also travelled for pleasure. As the children grew up, Edith often accompanied him to New York or Washington to shop, visit friends and attend plays, or she took journeys alone to visit children and other relatives. All the Duke children, as they reached their teens, attended boarding school, and all received at least some college education. Edith Duke died suddenly in 1921, and two years later, Tom married Maymee Richardson Slaughter, his wife's sister-in-law from Lynchburg. In March of 1926 Tom died at the age of 76.

Walker, after a few years in the Navy, joined the Army and became a career officer. Jack served in the Army during World War I, and then began a career in business. In 1917, Eskridge took a law degree at Virginia and joined his father's practice. He was plagued by ill-health throughout his career, and soon after their father's death, his sister Mary, a former social worker, began assisting in the law office. Helen, a librarian, worked in New York and Norfolk for a year or so before moving back to the family home. Eskridge and his wife, Lucy Lee, had three children, of whom two, William Eskridge Jr. (Bill) and Lucy Marshall, grew to adulthood. Jack died in 1933; Eskridge, in 1959; Walker, in 1960; Mary, in 1966; and Helen, in 1984.

The Charlottesville law practice established by R. T. W. Duke in 1850 remained in the family for two succeeding generations. After studying law with John B. Minor at the University of Virginia, Duke practiced alone until 1858, when he built his office at 20 Court House Square and took James D. Jones as a partner. Another lawyer, Louis G. Hanckel, joined the firm in the early seventies and handled insurance business. When Tom finished his legal studies in 1874, he assisted his father, whose partner by then was Stephen V. Southall. In the 1880's the firm was called Duke and Duke, William having joined his father shortly before Tom became judge.

The early work of the firm was limited to real estate, debt collection, and probate work, with an occasional criminal case. In addition, there was ample time for all three lawyers to pursue their assorted outside interests. At the office each man wrote his own letters, Tom switching to a Remington typewriter in 1889, before the days when they could hire a stenographer. The Dukes handled property rentals for some of their clients, the wealthiest and best known of whom was Jefferson Levy, owner of Monticello, the Opera House, and a great deal of other property in town.

With the combination of "the Colonel's" death, the social and economic changes in town around the turn of the century, and the energetic leadership of Tom, the workload of the practice increased and became more diverse. Loan and bond operations were added to the civil and criminal work and property management. Around 1917, Eskridge and Clarence E. Gentry joined the firm, now called Duke, Duke and Gentry. The law office was torn down in 1922, and the firm moved to a building shared with other lawyers at the corner of Fifth and Jefferson Streets. The practice flourished, and the Dukes often hired Virginia law students or graduates as clerks or associates, including Elizabeth Tompkins (the first female graduate of the Law School), Bernard Chamberlain, Anna Dinwiddie, and John Yancy.

It has not been determined whether the Dukes sold insurance after Hanckel left, but some time after Eskridge joined the firm in the late teens, the Insurance Agency was established. The title was changed to the Insurance Agency of Charlottesville in 1923, when W. F. Carter Jr. as agent. After Carter misappropriated funds, he was relieved of his job, the agency was incorporated, and the Dukes' interest in the business was eventually bought out by William B. Murphy.

Eskridge carried on the law practice with the assistance of Mary and an occasional associate. In 1937, he wrote that his firm "is regional and local counsel for a number of insurance companies, Virginia counsel for the Pike Coal Company, and does a general legal business, specializing in insurance, real estate, corporation and probate law, also maintains a collection department." With his failing health in the late forties, the practice dwindled until 1955, when Duke and Duke closed a little over a hundred years after it began.