Michael Shepherd

Michael Shepherd, a West Point graduate from the class of 2011, shares a profound connection with the Drew Ross Memorial Foundation through his enduring friendship with Drew. Their journey began at West Point, where they navigated the challenges of Cadet Basic Training (BEAST) together and shared the camaraderie of being part of company F4 from their Yuk through their Firstie years, proudly chanting, “Go Frogs!”

After graduation, Michael and Drew began their service to the nation at Fort Stewart, Georgia, as members of 6-8 CAV, 4th IBCT, 3rd Infantry Division—proudly embracing the designation of Mustangs. Their shared experiences deepened during a deployment to Logar Province, Afghanistan, in 2013, where they served as scout platoon leaders and both earned the Combat Action Badge and Bronze Star.

After serving five years, Michael left the army and attended law school at the University of Florida. There he met his wonderful wife, Jessica, who served as the athletic trainer for the Florida Gators women’s basketball team. Currently residing in Coral Gables, Michael is an Assistant United States Attorney and prosecutes federal criminal cases, while Jessica works for the Miami Marlins as their Player Health & Injury Analytic Lead.

Michael serves as the chairperson for United Way Miami’s Mission United legal services subcommittee, an organization that assists veterans in Miami-Dade County with a wide array of pro bono legal services. He also volunteers his time with the West Point South Florida Field Force, where he gives presentations and speaks with high school students who are considering attending West Point.