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Bennett-Fleming prepped for the political arena with a bachelor’s degree from Morehouse College, a law degree from the University of California, Berkeley, School of Law and a public policy fellowship at the Harvard Kennedy School of Government. As a student, he was the deputy national director of faith outreach for John Kerry’s 2004 presidential campaign, worked to get Maryland Sen. Benjamin L. Cardin elected and completed a fellowship on the House Financial Services Committee.
Bennett-Fleming also beefed up his résumé with top-notch private sector experience, including an internship at Goldman Sachs and law school apprenticeships at Patton Boggs and Alston & Bird.
His next move, at 25, was launching a bid against incumbent D.C. shadow Rep. Mike Panetta. Taking a page out of the playbook of former Rep. Harold Ford Jr., D-Tenn., who campaigned for Congress while finishing law school at the University of Michigan, Bennett-Fleming stacked his final semester of law school classes for the middle of the week so he could spend extended weekends campaigning in D.C. for the unpaid and largely unrecognized position.
Bennett-Fleming lost that campaign, but was successful when he tried again after Panetta called it quits.
“When you have a certain level of educational opportunity, it gives you a license to go out there and try to fall on your face,” Bennett-Fleming said. “It would have been more convenient to take a more private sector or even a more conventional public sector path, but I felt that I was equipped and I had a responsibility to try to take a more unconventional path that could potentially have a higher return for the people that I care about.”
Two years later, when Panetta was ready to give up his seat, he opted to support and informally advise Bennett-Fleming’s second bid. Bennett-Fleming won, running unopposed.
As “the low man on the D.C. electoral totem pole,” he’s used to being the last one to speak at events, being cut short by restless, disinterested crowds and “just simply working very hard and feeling under appreciated for your work.”
Since announcing his bid for the at-large council seat in November, Bennett-Fleming has been balancing his shadow representative role and his paying job as an adjunct professor at the University of the District of Columbia with campaigning.
He faces an uphill battle to defeat incumbent Councilmember Anita Bonds, who has more than three decades of experience in local government and politics. It’s a crowded field for the April 1 Democratic primary, including second-time candidate John F. Settles Jr., Latino activist Pedro Rubio and veteran Kevin Valentine Jr., according to the D.C. Board of Elections website.
Thirteen months representing the city’s 630,000-plus residents to Congress has been an “interesting training ground” for a career in public office, Bennett-Fleming said. Now he feels he could best serve his Southeast D.C. roots by trying to make sure everyone can benefit from the city’s recent prosperity.
As a councilmember, he would focus on education and business development, instead of just statehood, he said. He wants to create a city-run venture capital fund to encourage entrepreneurship and add more technology training to D.C. classroom curriculum.