Born and raised in Washington D.C., Leonard (Lenny) began boxing while at Coolidge High School. While working out at a local Catholic Youth Organization, Lenny was spotted by a boxing coach who took him under his wing. Soon thereafter, Lenny entered the ranks of amateur boxing. During his three years as an amateur, Lenny defeated every contender in the Golden Gloves heavyweight class. In 1954 he won the New York Golden Gloves Tournament of Heavyweight Champions and the Intercity Golden Gloves Heavyweight Championship. After joining the Marines, Lenny won both the Eastern Heavyweight Championship and the East-West Golden Gloves Championship. In 1956, he won the International Golden Gloves Championship. Lenny was offered a spot on the U.S. Olympics team. He declined, instead accepting a bid to turn professional. He won his first 10 professional bouts. He lost his 11th (and last) fight at Madison Square Garden by a split decision. After giving up his boxing career, he taught boxing courses at summer camps and taught classes in both boxing and racquetball at the JCC. In 1992, Lenny was inducted into the DC Boxing Hall of Fame as an amateur fighter.