Leonard, the fifth of seven children of Cicero and Getha Leonard, was born in Wilmington, North Carolina. He was named after Ray Charles, his mother's favorite singer. The family moved to Washington, D.C., when he was three, and they settled permanently in Palmer Park, Maryland when he was ten. His father worked as a supermarket night manager and his mother was a nurse.

On November 7, 1988, Leonard made another comeback, facing Don Lalonde at Caesar's Palace in Las Vegas. They fought for Lalonde's WBC Light Heavyweight Championship and the newly created WBC Super Middleweight Championship, which meant that Lalonde had to make 168 lbs. Many were critical of Leonard for stipulating that his opponent--a natural 175 pounder--should weigh less than his usual fighting weight, which could possibly weaken him. However, Lalonde later told HBO's Larry Merchant that he didn't have any trouble making weight.  Lalonde, 31-2 with 26 knockouts, was guaranteed at least $6 million and Leonard was guaranteed over $10 million.  This would be Leonard's first professional fight without Angelo Dundee. For Leonard's fight with Hagler, Dundee worked without a contract and received $175,000, which was less than 2% of Leonard's purse. Dundee was unhappy with that amount. He requested a contract for the Lalonde fight and Leonard refused. "I don't have contracts. My word is my bond", Leonard said. Janks Morton and Dave Jacobs trained Leonard for the Lalonde fight.  Lalonde's size and awkwardness troubled Leonard. In the fourth round, a right hand to the top of Leonard's head dropped him for just the second time in his career. Early in the ninth, Lalonde hurt Leonard with a right to the chin. Leonard fired back and hurt Lalonde with a right. He drove him to the ropes and unleashed a furious assault. Lalonde tried to tie up Leonard, but got dropped with a powerful left hook. He rose but was soon down again, and the fight was stopped. Judges Chuck Giampa and Franz Marti had Leonard ahead by scores of 77-74 and 77-75, respectively. Judge Stuart Kirshenbaum had Lalonde ahead 76-75.  After the fight, Leonard vacated the light heavyweight title, but kept the super middleweight title. Also, Leonard and Janks Morton split because of personal differences. Morton was replaced as co-trainer by Pepe Correa, who had worked with Leonard for most of the previous fifteen years.

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