Benitez, a young prodigy who was managed by his father Gregorio Benitez, was a member of one of Puerto Rico's most famous boxing families, his brothers Frankie Benitez and Gregory Benitez also being top notch contenders in the decade of the 1970s. The Benitez troop was also commandereed by their mother, Clara Benitez. He was nicknamed The Radar.
During the early stages of his professional career, Benitez often traveled to the Virgin Islands and New York, (where he was born), for fights. He divided his fights between those locations and Puerto Rico. The proximity of those two locations to Puerto Rico helped him start to become a household name in the island while building an international following at the same time. His stunning speed, combined with punching power and incredible ring maturity for a 15 year old, took the boxing world by storm. Benitez kept on winning, and in 1976, he lured the far more experienced, 2 time world champion and now member of the hall of fame Antonio Kid Pambele Cervantes of Colombia to San Juan's Hiram Bithorn stadium, to defend his world Jr Welterweight championship. Benitez stunned the world by beating Cervantes. Wilfredo won a 15 round unanimous decision, becoming the youngest boxing world champion in history, at the tender age of 17.
Benitez retained this championship 3 times, and then the lure of a Million Dollar fight with a certain 1976 Olympic champion named Sugar Ray Leonard, then made him move up to Welterweight. He and world champion Carlos Palomino, who hailed from Mexico but lived in Los Angeles, signed up for a title fight, which again was fought in San Juan, under the auspices of Goya Rice and Bacardi. It was another tough fight, but Benitez won a 15 rounds decision to become world champion for the second time. After a defense against Harold Weston Jr, which ended in a Benitez unanimous decision win, Benitez and Leonard signed for a fight in Las Vegas in November, 1979. It was a brilliant exhibition of scientific boxing by both, but Benitez unsuccessfully tried overcoming a 3rd round knockdown and a cut which was opened on his forehead by a headbutt in round 6, and the fight came to an end when the referee stopped the fight with 6 seconds left in round 15.
After that loss, Benitez moved up in weight, and in May 23,1981 he became the youngest 3 time world champion in boxing history, by knocking out world Jr. Middleweight champion Maurice Hope of Trinidad & Tobago, in 12 rounds in Las Vegas. This one was a frightening knockout,a devastating left hook to the face and Hope had to be hospitalized briefly after the fight. The knockout was named one of the knockouts of the year.
His next fight became a historic bout because when he met future world champ Carlos Santos of Ceiba, Puerto Rico , it became the first world championship fight between two Puerto Ricans in boxing history. Ironically, the fight was fought 3,000 miles away from Puerto Rico, in Las Vegas' Caesars Palace hotel, and Benitez won a 15 round unanimous decision. Then came Roberto Duran, beaten in the same hotel in 1982, but at the Carnival of Champions in New Orleans, Benitez had to give up his belt to that other boxing legend, Thomas Hearns, after a fight that featured knockdowns from both fighters, losing a 15 round unanimous decision.
Benitez's career went downwards after that night with Hearns, and so did his lifestyle. In 1984 , he tried a comeback under the hand of Yamil Chade but this proved to be unsuccessful. In 1987, with his health clearly declining already, he went to Buenos Aires, Argentina to fight Middleweight Carlos Herrera. Benitez was stopped in 7. But that wasn't the worst part of the trip. He got his money for that fight stolen by the promoter, along with his documents and passport, and was stranded in Argentina for 1 year. After much government huddle and talks, he was finally able to fly back home to Puerto Rico in 1988. One of the most touching moments in his life came when, upon leaving the airplane that brought him back, he handled his 7 year old daughter an Argentine toy doll he had bought for her before his fight there, and told her he hadn't forgotten her one single day during his time there.
2 years later he moved to Tucson, Arizona, where he tried another comeback under the tutelage of Emanuel Steward, the famous Kronk trainer. This also proved unsuccessful and he moved back to Puerto Rico, where he is now living with his mother Clara, on a 200 dollar a month pension provided by the WBC.