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Coach Robert "Bob" Headen, born November 26, 1939, is a third generation Washingtonian and former Denver Broncos running back in the American Football League. He retired from the District of Columbia Public School System after 40 years of services as Athletics Director, Dean of Students, teacher and coach in 2004. Coach Headen is considered a pioneer in developing girls' basketball in D.C., as well as the architect of Washington's most dominant program. He took over as Howard D. Woodson High School's girls basketball coach two years after the passage of Title IX—legislation that barred gender discrimination at schools that receive federal funds.

Headen is the winningest Football Coach in the history of D.C. public schools. Eighteen of his former players have been drafted in the National Football League (NFL). On June 26, 1996, he was the first African-American and the first Washington D.C. inductee into the National High School Coaches Association. Robert "Bob" Headen is, in every sense of the word, a DC Coaching Legend.