Denis Fleming Jr. was born in Portsmouth, Virginia, and raised in Virginia and Kentucky. He earned his bachelor's degree with distinction from the University of Kentucky and is a graduate of its College of Law. Fleming practiced law with the firm Barnett & Alagia and later served as counsel to Kentucky Governors Wilkinson, Jones and Patton and as chief deputy attorney general of the state. In 2004, he was appointed chief of staff to Cong. Ben Chandler in Washington, D.C. and later served as a senior officer and counsel to a national healthcare provider. His first book, Thomas Jefferson and the Kentucky Constitution, was published by the History Press in 2025. He resides in Washington, D.C., and Miami and has written published book reviews.