D.C. High School Coach Who Mentored 25 Future NFL Players Passes at 85

Bob Headen, who also had a legendary career as a girls basketball coach, won 284 games in the D.C. public school system

Bob Headen, who had a legendary coaching career int he District of Columbia, died in October at the age of 85. / D.C. Public Schools

Robert James Headen or Bob as he was known to his close friends and family was a legendary high school football and girls basketball coach in Washington, DC who died on October 15. He was 85. 

During his tenure, Headen, who would have turned 86 on November 26, compiled a 284-89 win-loss record on the District of Columbia Public School gridiron. 

Headen was the first African-Americn to be inducted in the NHSCA

Headen is widely known as the winningest football coach in the history of D.C. public schools. He was also the first African-American and the first Washington, D.C. native to be inducted into the National High School Coaches Association. 

He won eight DCIAA championships with the first coming in 1968

Headen, whose coaching career began at his alma mater Cardozo High School in Washington, DC, guided the Clerks to a 24-19 victory over McKinley Tech in 1968. That win marked Headen’s first D.C. Interscholastic Athletic Association football championship. He would go on to win a record eight DCIAA football championships. 

“Coach Headen and my father are the only two men I’ve ever been afraid of,” said Theophus Brooks, a 1968 Cardozo High School graduate who played for Headen.  

Brooks, who played two seasons on the Clerks’ varsity squad, recalled some fond high school football memories about his beloved head coach. 

“He used to grab me by my facemask and curse me out,” said Brooks, who played strong safety at Cardozo, “but I loved that man.” 

After a three year stint at Cardozo, Headen moved to H.D. Woodson where he won seven titles

In 1972, Headen accepted a teaching position at H.D. Woodson High School after three seasons of coaching football at Cardozo. 

During his tenure at H.D. Woodson, Headen served as head coach of the football program and the girls basketball program before he was promoted to Athletic Director. 

Headen guided H.D. Woodson to seven DCIAA football championships over the years. The football program captured titles in 1975, 1981, 1982, 1987, 1993, 1994 and 1997. 

Orlando Brown, Byron Leftwich and Josh Morgan are among 25 future NFL players he coached

Headen mentored many notable high school student-athletes during his coaching stints at Cardozo and H.D. Woodson including future NFL standouts Orlando Brown, Byron Leftwich and Josh Morgan. 

“He put a lot of guys in the pros,” said Brooks, “about 25 NFL ballplayers.” 

Headen also won more than 600 games as Woodson's girls basketball coach

Headen was also a successful girls basketball coach at H.D. Woodson. He coached UConn assistant coach and former UConn player Jamelle Elliott at H.D. Woodson. Headen’s girls basketball teams at H.D. Woodson compiled more than 600 wins including a pair of city title game championships during his tenure. He also guided the softball team to a pair of city championships. 

“Woodson was loaded with ballplayers,” said Brooks, “and he turned it into a powerhouse.” 

The stadium at H.D. Woodson High School has been dedicated to Headen and the legendary coach has received numerous accolades and honors including an induction into the inaugural District of Columbia State Athletic Association (DCSAA) Hall of Fame in 2017.