Teófilo senior arrived in Cuba in 1923, finding work wherever he could, before settling in Camagüey with Dolores, where he gave English lessons to top up his meagre earnings.

Due to his large size, Teófilo senior was encouraged into boxing by local trainers, fighting seven times before becoming disillusioned by the corrupt payment structure on offer to young fighters.

[4] Chervonenko, a retired boxer himself, sent by the Soviet Union, who had created Cuba's Escuela de Boxeo (Boxing school) in a derelict old gym in Havana, began to champion Stevenson's progress.

[5] Stevenson's senior boxing career began at age seventeen with a defeat in the national championships against the experienced heavyweight Gabriel Garcia.

Despite the setback, Stevenson went on to register convincing victories over Nancio Carrillo and Juan Perez, two of Cuba's finest boxers in the weight division, securing a place in the national team for the 1970 Central American and Caribbean Boxing Championships.

Stevenson easily defeated German Peter Hussing in the semifinal by TKO in the second round, and received his gold medal after Romanian Ion Alexe failed to appear in the final due to injury.

AIBA president Anwar Chowdhry, when asked did the Cuban authorities acted properly in giving Stevenson two houses and two cars, said: "These things should not be allowed.

Over tea in his office in Havana's Sports City Coliseum, INDER president Conrado Martínez Corona defended the local practice of giving cars and apartments to top athletes.

This was the point where he was the closest to signing a professional contract, as American fight promoters offered him US$5 million to challenge world heavyweight champion Muhammad Ali.

[8] If he had accepted, it would have made Stevenson the second boxer to go straight from the Olympics into a professional debut with the world's heavyweight crown on the line, after Pete Rademacher.

This fight ended an eleven-year unbeaten run by Stevenson and was the only occasion that he did not win the gold medal at the World Championships when he entered the competition.

[10] Stevenson might have won a fourth gold medal at the 1984 Summer Olympics, but the Soviet Union boycotted the games, which were hosted by Los Angeles, in retaliation for the American boycott of the 1980 Moscow competition.

[8] For consolation, he beat future Olympic champion Tyrell Biggs in February 1984 (breaking three ribs in the process) and won the super heavyweight gold at the 1984 Friendship Games, defeating Ulli Kaden of East Germany and, in the final, Valeriy Abadzhyan of the Soviet Union.

[11] At the 1986 World Amateur Boxing Championships, he won the super heavyweight gold, defeating Alex Garcia from the United States in the final.

Stevenson's second loss to Vysotsky happened six weeks before his knockout winning streak at the 1976 Olympics in Montreal, which ended up with victories over John Tate and Mircea Șimon.

Various western estimates totaling his record to 500+ fights,[15] including there hundreds of unaccounted tough sparrings with a degree of aliveness outstanding for amateur boxing, which paid off with such an excellent career (his fearsome reputation alone brought him 22 walkover wins, and a number of byes to skip unnecessary encounters with a limited opposition.)

Stevenson turned down several lucrative offers to go pro, which came from various internationally well-known U.S. boxing kingpins, most notably from Don King and Bob Arum.

[16] King's top rival Arum almost succeeded and came the closest to pulling off an Ali-Stevenson matchup when the Cubans accepted his $1 million offer for five three-round exhibition fights.

[7] Nevertheless, Stevenson's professional debut never did happen, because he remained loyal to the Cuban revolutionary ideals, never accepting any payday for himself, no matter how big it appeared.

After knocking out three opponents at the Munich Olympics in September 1972, including Duane Bobick of the United States, Stevenson was approached by an American promoter, who offered him $1 million to turn pro on the spot.

He worked at the National Institute for Sports, Physical Education, and Recreation (INDER,) also he served as vice president of the Cuban Boxing Federation.