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Leonard retired several times. After announcing his (first) retirement because of a detached retina, Leonard returned to fight Kevin Howard. He retired again after that bout, but returned almost three years later to fight Marvin Hagler. He retired again after that fight, but then returned about a year and a half later to fight Donny Lalonde. After drawing against Thomas Hearns and defeating Roberto Duran, Leonard lost to Terry Norris and retired for the fourth time. Six years later after fighting Hector Camacho, he retired for the fifth and final time.

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