Coach Bill Mcgregor has been coaching at Dematha for many years. He has won many championships but is mainly known for his coaching and producing great athletes like MarShawn Lloyd, Demarco Hellams, Nick Cross and more. He even left Dematha in 2002 for a period of time and came back in 2019 as the head coach, and they still were winning championships. He has won the NFLs best High School coaching award six times in a row according to the Washington Post. Every year the NFL recognizes DeMatha for the amount of players they send to the NFL.

Devon Bertrand, a varsity football player said “that Mcgregor wasn’t even thinking about the 300th win. He treated it like another game.” Coach McGregor treated the game like any other, despite the gravity of the impending achievement. After the game he said “I am happy but it is never about me, I’m not the one playing. I thank all my present and past players, the coaches, and the administrators for all your support.”