Richard Thomas Walker Duke, son of Richard and Maria Walker Duke, was born on June 6, 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, who 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 chose 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.

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.