Originally from Northern Virginia, Judge Winn Fleming Williams (retired) graduated from the University of Kentucky in 1971 with a double major in sociology and political science.   

Upon his graduation, he entered federal service in October 1974. After receiving his criminal investigator training at Quantico, Virginia, and the Federal Law Enforcement Training Center in Brunswick, Georgia, he became a federal law enforcement officer. During his federal career, he served in numerous capacities as a special agent and special agent in charge for law enforcement organizations across the country. He also served on many anti-terrorism and counter-terrorism, anti-gang, drug enforcement and white-collar crime task forces. His senior management skills and services were also lent to the White House, the Office of Management and Budget and the Nuclear Regulatory Commission.

After 9/11, he was recruited to assist in the creation of two new federal agencies, the Transportation Security Administration and the Department of Homeland Security. He became the first director of the DHS training academy in Artesia, New Mexico.

Since leaving federal service, Williams has been a program manager, director of operations, vice president and senior consultant for security contracting companies across the country. In August 2017, he was appointed as a Municipal Court judge, serving the municipality of Greer in addition to the counties of Greenville and Spartanburg, South Carolina.

Among Williams' many commendations are the President's Council on Integrity and Efficiency Award for Excellence, the U.S. Attorney’s Award for outstanding achievement, two Department of Homeland Security gold medals and the Department of Homeland Security’s highest honor, the Secretary's Excellence Award. He was also presented the University of Kentucky Distinguished Service Award in June 2019.

Within the University of Kentucky, he represents the College of Arts & Sciences for the UK Alumni Board, where he serves on the Leadership Advisory Council as well as the Diversity/LGBTQ committee. He is a past president of the UK Alumni Club as well as the president of the Kentucky Society, both in Washington, D.C. He lives outside Greenville, South Carolina.