Thinking back to his graduation from St. Andrew’s Episcopal School at Washington National Cathedral more than two decades ago, Nate Bennett Fleming ’02 mostly remembers feeling inadequate compared to his peers, and it had him peeved.

“There are some students that enter the cum laude society and they have the special ribbon, and there are some students that are asked to speak,” Bennett Fleming recalled this past March. “I was an ambitious student, and I didn't receive any of those accolades. I didn't speak, I wasn't in the cum laude society so I felt quite average, and I didn't like that. I remember that feeling – this was the end of my high school career, and I didn't do anything to separate myself.”

It became the fuel to Bennett Fleming’s fire as the disappointment turned into a chip on his shoulder the size of the DMV – a chip that drove him through his undergraduate studies and to a successful career as a lawyer, academic, and politician with advanced degrees from Harvard University, The University of California, Berkeley and the University of Pennsylvania.

Now, after not speaking or receiving any accolades at his high school graduation, Bennet Fleming served as commencement speaker for the Class of 2025 at Washington National Cathedral on June 6.

“My experiences – not just at St. Andrew’s — the challenges that I had to navigate to achieve some level of success, what I've learned through my commitment to giving back to the community and my unrelenting commitment towards achievement will allow me to impart something valuable to the graduates,“ Bennett Fleming said.

With ambitions to become a President of a Historically Black College or University (HBCU) like his undergraduate alma mater, Morehouse College, Bennett Fleming is currently an assistant professor of law at Wake Forest University. As an interdisciplinary constitutional law scholar, he specializes in state and local government law, the law of democracy, and issues of justice at the intersections of law, race, politics, and higher education. 

Prior to his current role, Bennett Fleming served as a shadow U.S. Representative for the District of Columbia –  an elected advocate to Congress on issues related to Washington, D.C., statehood and other federal matters. His work was instrumental in the passage of the historic D.C. Statehood legislation in the House of Representatives in both 2020 and 2021. He also served as a legislative and committee director at the D.C. Council, where he wrote several pieces of legislation to expand educational, housing, employment, and community equity throughout Washington, D.C.

“I haven't begun working on my speech, but I certainly (will draw on) my experience,” Bennett Fleming said when interviewed for this profile in March. “I wasn't a cum laude graduate of St. Andrew’s, I was more of a “thank you, lord” graduate of St. Andrew’s. But sometimes, when you come from a school with such a strong foundation, the ‘thank you, Lord’ graduate has the skill sets to be very successful.”