Upon being hired as the head football coach at Richard Montgomery High School in 1959, Roy Lester considered himself lucky. For starters, as he looked at prospective members of his team, Lester saw plenty of faces – which was far from the case at his first coaching position, where he had just 14 players on the team. And then, he noted, the team had plenty of talented players, including future NFLer Mike Curtis.

“When I went to Richard Montgomery, they hadn’t been winning anything,” Lester said. “I took [former Maryland players Rod] Breedlove and Ronnie Shaffer over with me in the preseason to help me out. They looked things over and said, ‘You’ll never win here.’ But I told them there was a kid there better than any player we had at Maryland – Mike Curtis. That’s luck.”

Leaning on Curtis, Richard Montgomery went undefeated in Lester’s first two seasons. Curtis went on to Duke University and was selected to the Pro Bowl four times in 14 NFL seasons, but Lester and Richard Montgomery continued their successful ways without their star. In all, Lester guided the Rockets to an 86-10-1 mark with six undefeated seasons before being hired as the head coach at the University of Maryland.

Following three seasons in College Park, Lester returned to the high school sidelines. He guided Paint Branch to the 1975 Class B state championship and he led Magruder to the Class B state championship in 1984 and the Class A state championship in 1986.

In 1984, the Touchdown Club of Washington selected Lester as its high school coach of the year.  Lester’s high school teams won 260 games. Lester is a member of Maryland Football Coaches Association Hall of Fame and the West Virginia University Sports Hall of Fame. Richard Montgomery named its athletic field Roy Lester Stadium.

“I think I had a good background,” Lester said. “Before I came to Montgomery County, I had coached in a couple impossible situations. I always studied the game close wherever I was and I enjoyed it. I didn’t mind working hard to get it.”



After the final game of his 36-year career as the head coach of the Georgetown Prep Little Hoyas, Jim Fegan insisted on business as usual. Sportsmanship was important to the man who was hired at the North Bethesda school in 1961 and turned it into a football powerhouse. Before any celebration, his players had to shake hands with their opponents.

Only then could the players hoist Fegan on their shoulders as the student body chanted: “Thank you, Mr. Fegan.”

When talking about Fegan’s career, perhaps the best way to sum things up is that he did it the right way. His teams had a record of 239-62-12, capturing 14 Interstate Athletic Conference championships with only two losing seasons. The 1970 team finished No. 1 in the Washington area in the midst of a 36-game winning streak that spanned five seasons. There were nine unbeaten seasons.

Throughout his tenure, Fegan maintained his trademark crew cut. But he was known for adapting to his surroundings, while at the same time retaining his strong work ethic and discipline. To this day, he remains as assistant athletic director and assistant football coach at Georgetown Prep.

"He teaches the best way any teacher can, by example," Reverend Thomas Roach, S.J., then-president of Georgetown Prep, told The Washington Post when Fegan retired. "By his attitudes toward his opponents. His attitudes when winning. His attitudes when losing. He's very demanding and exacting on the field, but right after the game he embraces his family. He talks to the kids a lot about sportsmanship. He's at mass every day. Young people look to us for cues, and we've been fortunate to have him at our school."

London Fletcher, Gallagher, Morgan Wootten and Doc Walker.

London Fletcher, Gallagher, Morgan Wootten and Doc Walker.


Joe Gallagher had a simple philosophy when it came to coaching: Be firm, but fair. He also had some clever sayings, as noted in a Washington Post story when he turned 90 a few years back:

  • “You win some, you lose some and some you should have never scheduled.”
  • “Never send a kid home from practice unhappy.”
  • “I might have lost the game, but I’ve never lost a party.”

Of course, Joe Gallagher did not lose many games. He coached the St. John’s College High School football team from 1947 to 1967, guiding the Cadets to a 171-32-10 record and a remarkable eight City Titles. And he was well known for his success as a basketball coach, with a record of 870-292 in 44 seasons before retiring in 1991.

Gallagher also is known for giving Morgan Wootten his first job as a high school coach, plucking Wootten from his position coaching at an orphanage and hiring him to be the St. John’s junior varsity football and basketball coach. The two later combined forces and started the first basketball day camp, the Metropolitan Area Basketball School. Gallagher is in the Naismith Memorial Basketball Hall of Fame after receiving the Morgan Wootten Lifetime Achievement Award in 2008.

Cato June and Stewart.

Cato June and Stewart.


Perhaps no person is better known as the public face of a school in the Washington area than Willie Stewart. For 29 seasons, he was the head football coach at Anacostia, turning the Southeast Washington school into a perennial contender in the D.C. Interscholastic Athletic Association.

But in addition to seeing former players go on to pro careers or turn into coaches, Stewart took pride in some simple achievements. In one of the city’s roughest neighborhoods, he was a father figure for hundreds of players and longed to see them better themselves. Twenty of his former players made it to the NFL or Canadian Football League, including All-Pro linebacker Cato June.

“Just being able to help those young men is fun for me,” he told NFL Films, which was drawn to the school to share Stewart’s story. “If I can change [or] turn a kid around or help a coach get better, so be it.”

Stewart first became a head coach at Eastern in 1976. He moved to Anacostia for the 1981 season and remained the head coach until 2009. In all, Stewart’s teams made 13 appearances in the Turkey Bowl, winning seven. Perhaps his most trying season came in 1993, when Stewart guided the Indians to a runner-up finish in the DCIAA. Four of his players were shot in separate incidents that season; the following year, he was presented the Giant Step Award for individuals or organizations who exemplify the ideals and provide the support necessary for student-athletes to achieve academic and athletic success.

“You can’t save everybody, but, believe me, I try,” Stewart said at the time.

In 2012, Anacostia named its football stadium after Stewart and he is there many Friday nights during the football season, serving as a volunteer assistant coach.