Leonard started boxing at the Palmer Park recreation center in 1969. His older brother, Roger, started boxing first. Roger helped start the boxing program, urging the center's director, Ollie Dunlap to form a team. Dave Jacobs, a former boxer, and Janks Morton volunteered as boxing coaches. Roger won some trophies and showed them off in front of Ray, goading him to start boxing.
In 1972, Leonard boxed in the featherweight quarterfinals of the National AAU Tournament, losing by decision to Jerome Artis. It was his first defeat. Later that year, he boxed in the Eastern Olympic Trials. The rules stated that a boxer had to be seventeen to box in international competition, so Leonard, only sixteen, lied about his age. He made it to the lightweight semifinals, losing a disputed decision to Greg Whaley, who took such a beating that he wasn't allowed to continue in the trials. Whaley never boxed again.
Sarge Johnson, assistant coach of the U.S. Olympic Boxing Team, said to Dave Jacobs, "That kid you got is sweet as sugar." The nickname stuck. However, given his style and first name, it was probably only a matter of time before people started calling him Sugar Ray, after the man many consider to be the best boxer of all time, Sugar Ray Robinson.
In 1973, Leonard won the National Golden Gloves Lightweight Championship, but lost to Randy Shields in the lightweight final of the National AAU Tournament. The following year, Leonard won the National Golden Gloves and National AAU Lightweight Championships.
Leonard suffered his last two losses as an amateur in 1973. He lost a disputed decision to Anatoli Kamnev in Moscow, after which, Kamnev gave the winner's trophy to Leonard. In Poland, Kazimier Szczerba was given a decision victory over Leonard, even though he was dominated in the first two rounds and dropped three times in the third.
Leonard won the National Golden Gloves and National AAU Light Welterweight Championships in 1974. The following year, he again won the National AAU Light Welterweight Championship, as well as the Light Welterweight Championship at the Pan American Games.
In 1976, Leonard made the U.S. Olympic Team as the light welterweight representative. The team also included Leon and Michael Spinks, Howard Davis, Jr., Leo Randolph, Charles Mooney and John Tate. Many consider the 1976 U.S. team to be the greatest boxing team in the history of the Olympics.
Leonard won his first four Olympic bouts by 5–0 decisions. He faced Kazimier Szczerba in the semifinals and won by a 5–0 decision, avenging his last amateur loss. In the final, he boxed the great Cuban knockout artist Andrés Aldama, who scored five straight knockouts to reach the final.
Leonard landed several good left hooks in the first round. In the second, he dropped Aldama with a left to the chin. Late in the final round, he again hurt Aldama, which brought a standing eight count from the referee. With only a few seconds left in the fight, a Leonard combination forced another standing eight count. Leonard was awarded a 5–0 decision and the Olympic Gold Medal.
Afterward, Leonard announced, "I'm finished...I've fought my last fight. My journey has ended, my dream is fulfilled. Now I want to go to school." He was given a scholarship to the University of Maryland, a gift from the citizens of Glenarden, Maryland. He planned to study business administration and communications.
He finished his amateur career with a record of 145–5 and 75 KO's.
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