[1][2][3] Kennedy ran successfully for Senate in a June 4, 1991 special election following the death of John Buchanan; he lost reelection the following November after redistricting placed him in the same district as William C. Wampler Jr.

During his tenure, Kennedy led the management of the paper-to-digital automated systems of the county's historic criminal and civil case files and real estate records from paper ranging from 1856 to digital media early in the 21st century.

He led a paradigm shift in the use of judicial information technology throughout Virginia on several fronts earning him regional, state, and national accolades during his tenure as an innovator and disrupter 'thought leader.'

Involved in the business community, Kennedy served on the board of Black Diamond Savings Bank until its successful and profitable merger, and several other entrepreneurial start-ups leading him to become a Napoleon Hill Scholar.

During his public tenure, Kennedy frequently reached out to offer STEM education the region's youth through NASA DEVELOP programs using satellite remote sensing data; an International Space Station downlink, including the first female commercial astronaut Anousheh Ansari, NASA astronaut Leland Melvin, a mock-up Robonaut-1, and Moon rock at the University of Virginia's College at Wise for thousands regional youth;  Aerospace Days at the Lonesome Pine Airport which included rockets, remote controlled jets, drones and other remote controlled flight vehicles for thousands of spectators; the first FAA-approved drone delivery flight at Lonesome Pine Airport; student space station experiments; student satellites to low Earth orbit launched from Wallops Island, VA; and hundreds of SpaceX Starlink accounts for rural Appalachian Mountain students.