The Gray Family of Winston-Salem, N.C., included Bowman Gray, Sr., (1874-1935), a banker and R.J. Reynolds Tobacco Company (RJR) executive; his wife Nathalie Fontaine Lyons Gray (1884-1961); Bowman's father James Alexander Gray, Sr., (1846-1918) founder of Wachovia Bank and Trust; the children of Bowman, Sr., and Nathalie, sons Bowman Gray, Jr., (1907-1969), RJR chairman and benefactor of Wake Forest University Bowman Gray School of Medicine, and Gordon Gray (1909-1982), who served as a federal government official during the Eisenhower Administration and President of the University of North Carolina system. The Gray family collection was gifted to Special Collections and Archives (Wake Forest University) by one of Bowman Gray, Jr.'s sons, Lyons Gray. The Graylyn Estate records are part of the University Archives (Special Collections and Archives).

Bowman Gray was born in 1874 in Winston, N.C. to Wachovia Bank and Trust co-founder James Alexander Gray and Aurelia Bowman. Bowman Gray attended the University of North Carolina at Chapel Hill from 1890-1891 before leaving to become a clerk at Wachovia. In 1895, he began working at R. J. Reynolds Tobacco Company as a salesman at RJR in 1895 and became a manager in 1897. His work at Reynolds moved Gray to Baltimore, where he met and married Nathalie Fontaine Lyons. The couple had two sons, Bowman, Jr., and Gordon while living in Baltimore, but the family relocated to Bowman, Sr.'s hometown in 1912 after Reynolds Company founder, Richard Joshua (R.J.) Reynolds, selected him to lead the company's finance division. After twelve years in this role, Bowman, Sr., succeeded Reynolds' brother, William Neal, as president of RJR.

Between 1927 and 1932, Bowman Sr. and Nathalie oversaw the construction of the family estate, Graylyn, located across from the Reynolda estate of R.J. and Katherine Reynolds. In 1935, two years after the Grays moved into Graylyn, Bowman, Sr., died of a heart attack aboard a ship and was buried at sea. He bequeathed $750,000 of RJR stock to be used for a charitable endeavor and the family eventually decided the money would be used to establish a four-year medical school. A stipulation for accepting the gift was to relocate to Winston-Salem, N.C. Wake Forest University, then known as Wake Forest College, agreed to relocate its two-year medical school from Wake Forest to Winston-Salem. The Bowman Gray School of Medicine and the hospital, which were followed by the whole university, have been key contributors to the area's economic infrastructure and community. Graylyn Estate was also donated to the Bowman Gray School of Medicine. In 1972, Gordon Gray purchased the home from the medical school and donated it to the University. The house was used for academic programs and student housing until 1980, when the top floor of the estate caught on fire. Following the fire, University president James Ralph Scales declared that the property would be restored to its original condition and repurposed.

Bowman Gray, Jr., was born in 1907 in Baltimore, M.D. to Bowman, Sr., and Nathalie Fontaine Lyons Gray. He attended the Reynolda School in Winston-Salem, Woodberry Forest School in Virginia, and the University of North Carolina at Chapel Hill. In 1929, Bowman, Jr., became a salesman with RJR and then vice-president(1949). He was appointed sales manager (1952) executive vice-president (1955). Gray was president of the company from 1957-1959, when he became chairman of the board and chief executive officer. He stepped down as chief executive officer in 1967 and remained chairman of the board until his death in 1969. Bowman, Jr., also served as an officer in the U.S. Navy Reserves. He was on active duty in Norfolk, Virginia., where he helped develop plans and procedures for Navy intelligence. In 1936, Bowman, Jr. married Elizabeth (Libby) Palmer Christian of Richmond, Virginia. They had five sons: Bowman III, Frank Christian, Robert Daniel, Lyons, and Peyton Randolph. In 1969, Bowman Jr. died at his Winston-Salem home, Brookberry Farm, and is buried in Salem Cemetery. Gray actively donated to local orphanages and schools and other philanthropic projects.

Gordon Gray was born in Baltimore, Maryland, in 1909 to Bowman, Sr., and Nathalie Fontaine Lyons Gray. Gordon Gray held a variety of public service roles in local and national politics. He represented Forsyth County in the North Carolina General Assembly twice, from 1939-1943 and 1947-1949. Gray served in the U.S. Army and was appointed to Assistant Secretary of the Army (1949-1950), he was director of the Office of Defense Mobilization (1957-1958) and served as National Security Advisor (1958-1961). In 1961 he was awarded the Medal of Freedom and served on the President's Foreign Intelligence Advisory Board. In 1976, he was awarded the United States Military Academy's Sylvanus Thayer Award. Gray served as chairman of the board of Piedmont Publishing Company and was also publisher of the The Winston-Salem Journal. In 1938 he married Jane Boyden Craige and they had four sons: Gordon, Jr., Burton, C. Boyden, and Bernard.

Lyons Gray was born to Bowman, Jr. and Elizabeth (Libby) Palmer Christian Gray in Winston-Salem, N.C. in 1942. He attended the Wooster School and graduated from the University of North Carolina at Chapel Hill. From 1964-1965, Lyons served in the U.S. Coast Guard. Gray also served as a government official in several different capacities: as a Republican in the North Carolina house of Representatives (1989-2002), as a Chief Financial Officer of the Environmental Protection Agency (2005-2009) during the George W. Bush Administration, and the N.C. Secretary of Revenue (2013-2016). Currently, Lyons has been a N.C. Public Utilities Commissioner since 2016.

Constance (Connie) Fraser Gray graduated from Queens College, now Queens University, in Charlotte, N.C., in 1969, and worked as an administrative assistant at the Reynolda House Museum of American Art. She and Lyons were married in 1971. Connie served as a Wake Forest University Trustee and was selected by President James Ralph Scales to chair the Graylyn Advisory Committee after the fire in 1980. After determining that using the estate as a conference center would best serve the university and community, Connie served on the interior decorations committee to ensure the modern furnishings still complimented the Norman Revival architectural style of the home.

James Alexander Gray, Jr., (1889-1952) was the eldest son of James A. Gray, Sr., and Aurelia Bowman Gray. James, Jr., was born in Winston, N.C. where he lived and attended the West End Public School. He graduated from the University of North Carolina at Chapel Hill in 1908. He began his business career at Wachovia Bank where he served as a clerk, assistant treasurer, vice-president (1915), and a director (1918-1952). During this period Gray was president of the North Carolina Bankers Association (1918–1919) and a member of the executive council of the American Bankers Association (1920–1921). In 1920, James, Jr., joined RJR where he served as vice-president (1934-1946), company director (1946-1949), and as chairman of the executive committee from 1949 until his death in 1952. He married Pauline Lisette Bahnson in 1918 and the two had three sons, James III, Howard, and Bahnson, and three daughters, Emma, Pauline, and Aurelia.