Retirement, a permanent one at that, was Leonard's only option after suffering the most traumatic loss of his memorable career when Hector "Macho" Camacho, the International Boxing Council middleweight champion, hammered him to defeat after 1min 8sec of round five.
Playing the numbers game on his first professional visit to the east coast gambling capital, Leonard discovered that 40 was anything but lucky for him. In his 40th fight at the age when life is said to begin, Leonard gambled like a novice and paid with his livelihood.
His first mistake was believing that a damaged right calf, hidden as his pre-fight training was conducted behind closed doors, would not hamper his performance. The second was thinking that Camacho, naturally smaller, lacked the power to hurt him. The third was believing that a six-year lay-off could be offset by three months of training.
These miscalculations combined saw Leonard stopped for the first time in his 20-year career, ending the six-times world champion's dream of further glory. Leonard simply could not compete with a fired-up Camacho, so hyper that an hour before fight time the Puerto Rican New Yorker charged into the ring dressed as a Roman centurion, pumping his first in the air and yelling his trademark slogan: "It's Macho Time!" and soon it would be.
Unknown to the crowd of 10,324 at the Convention Center, Leonard, seemingly in excellent physical condition, had strained a muscle in his right calf in early February and needed cortisone and pain-killing injections to go through with this fight. But his mobility was severely hampered, leaving him a sitting target for Camacho's southpaw left-handers, and Leonard's own punches missed repeatedly as he struggled to regain the timing lost in his six-year absence.
Of the four completed rounds, Leonard perhaps won the second. But by the fourth he was stumbling like a Boardwalk drunk, losing balance whenever Camacho connected, and in the following round a beautifully delivered left uppercut dropped Leonard to the canvas, more hurt than at any time in his career. Bravely, he staggered to his feet as referee Joe Cortez's count reached six, but Camacho hammered Leonard on the ropes with two- fisted barrages that left Cortez no option but to rescue the Sugarman from further punishment.
Limping rather melodramatically into the post-fight press conference, Leonard announced what the gathered media already knew, "that's it from me," he said. "I'm out. It doesn't take a rocket scientist to know I should retire after a loss like that. Trying to defy the odds is one thing, but there comes a point where you realise that you just don't have it anymore."
He claimed that his calf gave way during the first round, but said that injury and inactivity should not detract from the finest performance of Camacho's 68-fight career. "Inactivity is the biggest sin in boxing," Leonard said. "But please don't say that I lost because of my injury. I lost to the better man."
For so long the bad boy of American boxing, Camacho, who has a catalogue of criminal misdemeanours to his name - his cut man Maximo Vasquez was arrested on the eve of the fight for allegedly conspiring to distribute 20 kilograms of cocaine - fought the perfect fight.
But the father of three, whose oldest son, 18-year-old Hector junior, almost made the US Olympic squad for Atlanta, has recently married his "number one homegirl" of 14 years, Amy Torres, and claims this victory can give him a fresh start in life.
He explained: "I used to party more than train. I'd spend four weeks training and 12 weeks partying. I was never home, always running around in the wrong places. I took advantage of my fame.
"But I am 34 years old and it is time to make up for the things I left behind. I want to be a better example for my kids."
Leonard, ever the media darling and anxious to prove himself a gracious loser supported Camacho's professed desire to change. "They look at his antics, not his talent," said Leonard. "This man has been ostracised, misunderstood, criticised, but you can't disguise his talent."
Neither can you disguise that one of the great boxing talents of all time, that of Ray Charles Leonard, has dissipated beyond even his remarkable powers of recovery. An era in boxing history has finally come to an end.