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Mike Trainer, the homegrown architect of Sugar Ray Leonard’s uniquely prosperous pro boxing career, swears he never intended to play Colonel Tom Parker to Leonard’s Elvis. Things just worked out that way.

It was 20 years ago this summer when Leonard’s fancy footwork and wondrous one-two-threes first struck the public’s fancy. He won a gold medal in the most brutal of Olympic events, with pictures of his family taped to his sweatsocks. But the typical pug pundits weren’t nearly so overwhelmed by the slight, baby-faced teenager from Palmer Park as were the fans. Then, as now, Don King and Bob Arum were pro boxing’s most powerful promoters and the sport’s only recognized idolmakers. Like the supposed experts, the sleazy sovereigns of the sweet science slobbered over bigger, far less winsome members of what is still regarded as the greatest U.S. amateur team of all time. The already toothless Leon Spinks and his brother, Michael, along with Howard Davis, quickly became cogs in the King and Arum promotion machines. Leonard remained a free agent long after the Olympic flame was doused.

When the Montreal games ended, Leonard announced that he was done with boxing. Janks Morton, who ran a local gym where Leonard trained, contacted Trainer. At the time, Trainer, a Bethesda native, was running his own general law practice in Silver Spring. His ring-friendly name notwithstanding, Trainer had no connection to the fight game, and had never even met Leonard.

“I was handling any legal case I could at the time—real estate, personal injury, criminal cases, divorces,” Trainer recalls. “But I had never done anything with sports or boxing. I only knew Janks because we played softball together. Janks was just asking people he knew to help Ray find a job, and I said I’d do what I could.”

With Trainer’s assistance, Leonard got work with Parks and Planning, the agency that runs recreation centers for Montgomery and Prince George’s Counties. Trainer also used his connections at his alma mater, the University of Maryland, to procure a nonathletic scholarship for Leonard.

Within months of his “retirement,” Leonard’s father became seriously ill. Around that time, it also came out that Leonard’s girlfriend and infant son were on welfare. Local fans put heavy pressure on him to reconsider his vocational plans. Leonard unretired from boxing, for the first of too many times in his career.

As word of his intentions to lace up the gloves as a pro got out, management and promotion offers were tendered from then-burgeoning sports magnate Abe Pollin (the Capital Centre had opened only a couple years earlier), Don King, and legendary Ali cornerman Angelo Dundee. Because he’d been helpful in procuring the rec center job and UM scholarship, Leonard went back to Trainer for advice on how to choose a manager.

“We really thought Angelo Dundee was going to be the guy,” Trainer says. “I was just going to be the attorney who got it all started. But then we found out that Angelo, for all the fighters he’d trained, had never managed a single fighter in his whole life! We’d interviewed him extensively, and that was the one small detail of his résumé that he neglected to tell us. So we wrote him off.”

By the time they saw through Dundee’s stick-and-move, Trainer had booked Leonard’s professional debut for the Baltimore Civic Center on his own. Figuratively and literally, the event was a knockout for Leonard. His next several fights, also booked by Trainer, were equally successful in and out of the ring. Trainer, by default, had become manager and promoter for the fighter who was quickly becoming the hottest property in boxing. He let the rest of his law practice all but collapse, and Leonard, fighting as a welterweight, became his one and only client.

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“We really didn’t know if we were doing things right or wrong—we didn’t know what we were doing,” Trainer says. “I found out pretty quickly that, okay, so maybe putting on boxing matches isn’t like launching a rocket. Unlike contracts with any other sport, in boxing, nothing is standard. Nothing. So, you negotiate everything. You go to the opponent and work that deal, then you go to the arena owner and work out that deal, and you go to the TV guy and make that deal. On the one hand, that was very exciting for us. On the other, it was frightening, because I was absolutely winging it. But a few months into it, Ray and I looked back, and there was just no turning around.”

King and Arum, looking to punish Leonard and Trainer for having ignored boxing’s established fighter/manager/promoter schemes, used below-the-belt tactics in hopes of freezing them out of the big-time. But that strategy fell apart as Leonard, by knocking out every opponent Trainer set in front of him, became such a big draw that the established mavens couldn’t ignore him.

“Those guys [King and Arum] tried to sign up every fighter that they thought we might want to fight,” Trainer says. “They’d look at all the fighters out there, try to guess where our next move would be, and then go give that fighter a few thousand dollars to get an option on his next few fights. That’s why Ray used to fight in different weight classes. It wasn’t because he couldn’t keep the weight off; it was because they signed up all the welterweights.”

Finally, in 1979, the freeze-out ended. King saw it was in his best interest to cave in to public pressure and give Leonard a title shot against one of his fighters, Wilfredo Benitez. On network television in prime time from Las Vegas, Leonard KO’d Benitez in the 15th round (title fights weren’t reduced to 12 rounds for another three years, after Duk Koo Kim’s death). Before any bells had been rung, Trainer had effectively KO’d King: While King had the fighter with a title and supposed boxing savvy on his side, Trainer had the much hotter commodity. So, King agreed to make Leonard the first nonheavyweight ever to get a million-dollar payday.

“What a great night that was, for the both of us,” Trainer says of the Benitez fight. “That meant he’d done everything we’d set out to do. Ray won a title, he was a millionaire, and he really never had to fight again. All from that one night! He didn’t quit, but he could have, and we’d worked so hard to get to that point.”

Trainer watched Leonard’s first title fight—and all subsequent bouts—on television in the locker room. Over the next 13 years, Trainer chose that same vantage point while his charge took part in some of the biggest events boxing had ever seen: Leonard-Duran I and II, Leonard-Hearns I and II, Leonard-Hagler.

“As soon as Ray left the dressing room to go to the ring to fight, my job was over,” he explains. “I felt that was his time, his moment. I didn’t want to take anything away from that.”

Because of Leonard, the sport’s little men were suddenly commanding heavyweight attention—and heavyweight cash—for the first time. Leonard’s squeaky clean image, enhanced to the nth degree because Trainer kept the fighter away from the Kings and Arums of the sport, led to the mainstream appeal. It was a lucrative strategy. Leonard pocketed more than $10 million from his third title defense, the first Duran fight, which also turned out to be his first loss.

But his best payday?

“Oh, that was for Donnie LaLonde,” says Trainer. “Remember him? The Golden Boy from Canada. Nobody believes me, but I swear to you that was Ray’s biggest purse. I’m not going to name numbers here, but it was well over the $10 million he got from the first Duran fight. We got a good deal.”

By the time Leonard’s final (well, apparently final) comeback ended with a loss to Terry Norris, his career take-home pay, not including any of his many endorsements, was in excess of $100 million. No other fighter in the history of boxing—regardless of weight class—ever banked so much just from fighting fees. Certainly none of his contemporaries even came close: Tommy Hearns and Leon Spinks are still fighting for chump change; Benitez is back in his native Puerto Rico, broke, punch-drunk, and barely alive.

Leonard is now living in Southern California, trying to follow Marvin Hagler into an acting career. Trainer still occasionally acts as Leonard’s agent, and in that capacity goes over the infrequent entertainment contract. But, like the only fighter he ever represented, Trainer, at 55, is out of boxing. His current calling is to spend the money that he earned—but never had time to spend—while Leonard was active. Even if he took just a fraction of the 50/50 split that King and Arum are accused of heisting from their fighters, Trainer’s got a nice nest egg.

“I do what I want now, because I can,” he says.

That means a lot of golfing in Florida. When he’s in town, Trainer periodically drives his high-end Mercedes convertible to the modest office he keeps in Bethesda. The walls there are laden with souvenirs from Leonard’s career, including a few pairs of boxing gloves and newspaper clippings from his biggest fights.

Despite all the memorabilia, Trainer contends that he doesn’t pine for the old days, good as they were.

“Ray Leonard is my legacy….” he says. “He was the reason people picked up my luggage at hotels and airports. I knew that. It was a good ride, but he walked away from boxing with his health and his looks and his money. That’s like a perfect ending, for him and for me. I’m done with boxing. I mean, how many times do you want to go to Vegas?”—Dave McKenna