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On May 1, 1986, Leonard announced on a Washington, D.C. talk show that he would return to the ring to fight Hagler. The announcement generated a lot of controversy because of Leonard's inactivity and eye injuries, yet it also excited many sports fans who had hoped to see them fight years earlier. Hagler took a few months to decide, then agreed to the match. The fight was promoted as "The Super Fight" and Leonard was guaranteed $11 million. Leonard was awarded a controversial split-decision.Jim Murray, long-time sports columnist for the Los Angeles Times, wrote, "It wasn't even close...He didn't just outpoint Hagler, he exposed him. He made him look like a guy chasing a bus. In snowshoes.... Leonard repeatedly beat Hagler to the punch. When he did, he hit harder. He hit more often.... He made Hagler into what he perceived him to be throughout his career-a brawler, a swarmer, a man who could club you to death only if you stood there and let him. If you moved, he was lost."
Often regarded as one of the greatest boxers of all time, he competed from 1977 to 1997, winning world titles in five weight divisions; the lineal championship in three weight divisions;] as well as the undisputed welterweight title. Leonard was part of "The Fabulous Four", a group of boxers who all fought each other throughout the 1980s, consisting of himself, Roberto Durán, Thomas Hearns and Marvin Hagler.
Leonard is also the godfather of Khloé Kardashian and has appeared on many episodes of Keeping Up With The Kardashians.
In his autobiography The Big Fight: My Life in and out of the Ring, published in June 2011, Leonard reveals that as a young boxer he was the victim of sexual abuse from an Olympic trainer as well as another man, a benefactor. He has since made public appearances to bring attention to the issue of child sex abuse, declaring himself a "poster child" for the cause and encouraging victims to report their abuse.