Despite his remarkable achievements, Sugar Ray Leonard still harbours regrets about one fight in particular where the result could have quite easily swung in favour of his opponent.
Throughout his decorated career, Leonard suffered just three defeats – against Roberto Duran, Terry Norris and Héctor Camacho – in all of his 40 professional outings.
The first of which came in 1980, back when the American neglected his typically crafty tactics, and instead decided to go toe-to-toe with his more rugged opponent.
As a result, Duran emerged from their first encounter with a unanimous decision victory through 15 rounds, before capitulating in their immediate rematch at 147lbs.
That time around, Leonard had implemented a more calculated gameplan, and in doing so was able to reclaim his WBC title with an emphatic eighth-round stoppage victory.
As for his defeats to Norris and Camacho, which both arrived at the end of his career, ‘Sugar’ was never able to exact his revenge.
The one fight that seems to have left a stone in his shoe, however, is his rematch with Thomas Hearns, which saw Leonard come away with a highly controversial draw in 1989.
Leonard had stopped his rival in the 14th round of their thrilling encounter in 1981, but up at a catchweight of 164lbs and nearly a decade later, he was simply not quite so effective.
Many thought that Hearns, the natural super-middleweight, had done enough to claim a points decision, and even Leonard himself has admitted to Harvard Business Review that he should have suffered a fourth professional defeat.
“I regret the ones I lost: Héctor Camacho, Terry Norris, the second fight with Tommy Hearns (which I won on [one] scorecard, but which he really won as far as I’m concerned).
“Looking back, I do have regrets, but I wouldn’t be the person I am today if I hadn’t gone through it.”
Many fans in attendance were furious with the outcome, with Leonard’s honesty a refreshing change for most boxers.