Cigar Aficionado

You knew business was down, but until the boss said you'd be flying to Las Vegas for a motivational speech by Sugar Ray Leonard, you hadn't realized how bad things really were. But you do know that Sugar Ray was a champion like few others, and you suspect that he'll kick your ass into next week—when business will be back up, or else.

When his name is introduced over the PA system, he steps to the stage as he once entered boxing rings: to thunderous applause. A champion of champions, with a boxing legacy written in sweat and blood and an aura that's larger than life, his confidence, charisma and energy are contagious.

Yet, he looks smaller than your memory of him when he was knocking someone out in a televised fight. It isn't long before your imagination takes over and you're in red boxing gloves and white trunks with black trim. Your heart races and your self-confidence surges as you await the opening bell of Round 1. In the opposite corner: Sugar Ray Leonard.

"I know exactly what you guys are thinking," says Sugar Ray, as the applause dies down. "You're thinking, 'Sugar Ray? He's not that big. I bet I could take him.'"

The thought that you might beat up on a 5-foot-10-inch, 160-pound man is understandable. Understandable, that is, if the man you were thinking of had not conquered the sport of boxing. Leonard, who won a gold medal at the 1976 Olympics, remains the first and only fighter in history to win world titles in five different weight classes and, along with being named Fighter of the Decade for the 1980s by Ring Magazine, was inducted into the International Boxing Hall of Fame in 1997.

His style combined speed and strength, unwavering discipline and determination, and an instinctive ability to take advantage of an opponent's weaknesses. His physical and mental preparation leading up to a fight were second to none. He was always running that extra mile or hitting the heavy bag for an extra round, never cutting corners or taking an opponent lightly.

It's this work ethic that makes Leonard who he is today. What began in the boxing ring has carried over into every role he's played outside of fighting: from family man to businessman, from boxing commentator and analyst to boxing promoter, from mentor and host of the reality television series "The Contender" to motivational speaker with the reputable Washington Speakers Bureau.

"Boxing has given me an incredible ride," he tells his audiences at venues that range from Fortune 500 headquarters to beer wholesalers' conventions. "It's afforded me the opportunity to escape poverty, to travel the world and meet important people like Nelson Mandela, but it's also taught me that the same principles that I applied to become world champion are applicable in the success of life and business.

"Just imagine the obstacles that you can overcome in your life," he adds, "if you take the same qualities of that confident boxing champion and apply them to every aspect of your daily life, be it business, family or athletics. I'm talking about endless possibilities for success."

His speech is entitled "P.O.W.E.R.: Prepare, Overcome, Win Every Round," and Sugar Ray Leonard has practiced what he preaches his entire life. Leonard, the confident champion, continues on the road to success outside the ring. But, as he tells his audiences, he has had to remain a fighter to do it.

Sugar Ray Leonard is enjoying the late summer sunshine at his Southern California home, laughing and talking openly about his career and his life. His affable personality and charming smile aren't what you would normally associate with a professional boxer. He's outgoing and relaxed, and definitely someone you wouldn't mind smoking a cigar with.

One wonders if this same public face is what had lulled some of his opponents into thinking Leonard would be a pushover inside the ring, that they wouldn't have to train hard to beat the amiable boxer. Certainly some members of the audience at his speeches these days are deceived into thinking they could outfight him. "I'm a pretty nice guy outside the ring," says Leonard, who at 50 still has the shoulders, biceps and forearms to combination-punch a Mack truck dead in its tracks. "But inside the ring? Whoa. I always felt that it was a transformation. I would go through a metamorphosis like Dr. Jekyll and Mr. Hyde."

Leonard says the change was achieved by a simple formula: determination, preparation and confidence. It's Leonard's philosophy that determination leads to preparation and preparation leads to the ability to overcome challenges, which then leads to confidence and, ultimately, to success. "Some of us are born with extraordinary size, strength, speed and talent," he tells his audiences. "But without determination, that talent never hashes out. No one is born a world champion. The successful do what they must to be number one."

Though it might be hard to believe, Leonard wasn't born a world champion. In fact, his boxing career had a dubious start. At the age of eight, Leonard watched older kids boxing at the local Boys Club in Washington, D.C., and decided that he wanted to lace up the gloves too. In his first fight he "boxed some kid with gloves on that were bigger than my head," and after taking several blows to the face, Leonard threw in the towel and went home with a splitting headache. "That was my first official retirement from boxing," Leonard says with a laugh. "I didn't pick the gloves up again until I was 14 years old."

When Leonard finally laced up again, there was no stopping him. "It was amazing," says Leonard, recalling the day he followed his older brother, Roger, down to the gym in Palmer, Maryland, a lower-middle-class suburb outside of Baltimore, into which his family had recently moved. "All of a sudden I found this sport again, or rather the sport found me. And this time I was ready for it."

Under the tutelage of Dave Jacobs and Janks Morton, two volunteer boxing coaches, Leonard began training like someone possessed. Instead of partying with friends or chasing girls, he dedicated himself to the gymnasium, learning the ropes and training ad nauseam. Instead of taking the bus back and forth to school, Leonard was running the distance. "I found the sport that I loved," says Leonard, "and I kept training and training and training. Even at the age of 14, I had discipline, motivation and determination. All those traits that make a champion."

Over the next six years, Leonard used these traits to become one of the most well-tooled and feared boxers on the amateur circuit, and a champion, to be sure. Fighting as a junior welterweight (139 pounds), Leonard won three National Golden Gloves titles, two AAU (Amateur Athletic Union) championships and a gold medal at the 1975 Pan-American Games in Mexico City. But the highlight of his amateur career, which comprised an astounding 145 wins, 5 losses and 75 knockouts, was his performance at the 1976 Summer Olympics in Montreal.

Without losing a round, Leonard cruised into the final, where he faced Andrès Aldama, of Cuba, who had battered his previous opponents, sending several away on stretchers. Despite Leonard's earlier success, his opponent was the prohibitive favorite for the gold medal.

Leonard had other ideas: "Around the time of the fight, it was like, 'No way. Ray can't beat this guy,' and I really caught onto that. Even back [home] in The Washington Post they predicted I would lose. But I was so confident. I knew it would be tough, but I had no doubt I would win the fight." Win he did. Fighting on national TV and with his family and friends in the crowd, Leonard soundly defeated Aldama in a unanimous decision.

The upset shocked the boxing world, but even more shocking was Leonard's post-fight interview with Howard Cosell, who had been touting Sugar Ray as a lighter version of Muhammad Ali. The winner told the announcer that he would retire from boxing. "It was a bittersweet moment," remembers Leonard. "I had no intention of turning professional, so as happy as I was winning the gold medal, I was unhappy because I knew it was my last go-around. That was it."

Leonard returned home to attend college and get a job. (As the story goes, Leonard received an athletic scholarship to the University of Maryland, which didn't even field a boxing team.) He also expected to reap the benefits of endorsements, but deals with Wheaties and others never materialized. Many, including Leonard, believe the deals dried up because his girlfriend, Juanita Wilkinson, had given birth to their son, Ray Jr., out of wedlock. "It's acceptable now," offers Leonard, "but back then, corporate America was very sensitive towards it."

Then came the moment boxing fans figured was inevitable: Leonard turned professional. Leonard admits the decision was made for financial reasons, but not that it came because he couldn't land endorsement deals. Shortly after the Olympics, Leonard's father entered the hospital and later lapsed into a coma. To help pay mounting medical bills, Leonard entered the pro ring for its promise of quick money. He hired an attorney, attained the services of Angelo Dundee, Ali's former trainer, and began training for his first pro fight, which he would win by unanimous decision on February 5, 1977.

As he'd done as an amateur, Leonard quickly made a name for himself in the professional ring. He had won his first 25 fights and was considered a contender to be reckoned with when Wilfred Benitez, the undefeated WBC welterweight champion, came calling. On November 30, 1979, Leonard answered with a technical knockout in Round 15.

Leonard was champion for just seven months before being dealt his first professional loss, by Roberto Duran. In a fight that Leonard once described as a "street brawl," he and Duran matched each other blow for blow through 15 grueling rounds, before the judges unanimously scored the fight in Duran's favor. "The fact of the matter is, Duran had a couple of rounds in his pocket before the first punch was thrown," admits Leonard in his motivational speeches. "I lost that fight because I lost my composure. He took me out of my plan. I poured my heart out, I just fought the wrong fight."

"You can't have success until you've known failure," he tells people. "And great motivators will tell you your past does not equal your future unless you want it to."

Leonard, of course, was not about to replay the past in a rematch with Duran. He intensified his training and saw his defeat against Duran's "hands of stone" as a blessing. He became more determined than ever. "My strongest trait has always been recognizing the weaknesses of my opponents and attacking them," says Leonard.

In the case of Duran, that meant getting into his head. "My strategy was to frustrate him, to make him lose his composure," Leonard says. "I did better than that. I made the guy quit." Throughout the fight, Leonard ceaselessly taunted Duran. He even windmilled his right arm as if he was going to throw a bolo punch, then jabbed Duran in the face with his left. After Round 8, Duran was so frustrated he refused to answer the bell, famously shouting, "No mas! No mas!" "I drove him crazy," Leonard says with a satisfied laugh. "I really pissed him off."

Although Leonard fought only nine more times during the '80s (eight of them victories, one a draw), many consider these fights to be among the greatest boxing performances of the last 30 years. One of the most notable is his 1981 fight against Thomas "Hit Man" Hearns in Las Vegas. With Leonard holding the WBC welterweight title and Hearns holding the WBA welterweight title, the unification fight was billed as "The Showdown." It would become Ring Magazine's "Fight of the Year," and is remembered today as one of the best fights ever.

Leonard remembers it the same way, but also recalls fighting back from the brink of defeat. After 12 rounds, Leonard's left eye was badly swollen and Hearns led in scoring. In his corner, Dundee began lacing into him, "You're blowing it, son! You're blowing it!" Leonard was exhausted, but he had prepared and trained for such a moment, when he had to dig deep inside himself and find the strength to overcome the obstacle before him.

"The greatest thing about the roadwork," says Leonard of the extra miles he ran and extra rounds he sparred, "is how it positively affects your confidence and gives you the ability to dig deeper and perform in high-pressure situations." Leonard knew that extra strength was there and he found it, knocking down Hearns in the 13th round and scoring a TKO in the 14th for the victory.

Leonard's finest hour, however, came in his fight against Marvelous Marvin Hagler in 1987. After defeating Hearns, Leonard fought one more time before suffering a detached retina, which forced him to retire from boxing in 1982. He returned for one more fight in 1984, but retired again. By 1986, the boxing world wanted one thing: Leonard versus Hagler. Pound for pound, they were the best in boxing, but Leonard hadn't fought in almost three years and his eye was still a major concern. Still, with promoters dangling $10 million in front of him for the fight, Leonard couldn't refuse.

"My comeback against Hagler was huge," says Leonard. "A lot of people were doubting me, and rightfully so. It had been three years since my last fight, so no one thought I could do it." Hagler was a heavy favorite, but Leonard once again set out to prove people wrong and, as usual, put his determination to work. "To beat a guy like Hagler, you do things twice as hard and twice as long," he says, "so in training camp, instead of doing three-minute rounds with one minute rest, I was doing six-minute rounds with 30 seconds rest."

The roadwork paid off. After 12 rounds of toe-to-toe action, Leonard was awarded the split decision. Hagler bitterly disputed the verdict (he would never fight again because of it) as did many boxing critics and fans. For Leonard, "it was a big, big feather in my cap" and, to this day, he claims that if you think Hagler won the fight, you don't know boxing.

Leonard retired once more after his fight with Hagler, only to return in 1988 to beat Don Lalonde for the WBC light heavyweight and the WBC super middleweight titles. In 1989, he fought Hearns for the second time (the fight ended in a draw) and Duran for the third, a fight Leonard won by unanimous decision. The final two fights of his career were losses, to Terry Norris in 1991 (after which Leonard retired yet again) and to Hector "Macho" Camacho in 1997, at the age of 40. His final professional record stands at 36 wins, 3 losses, 1 draw and 25 knockouts, with the WBC and WBA welterweight titles, the WBA light middleweight title, the WBC middleweight title, the WBC super middleweight title and the WBC light heavyweight title all to his credit.

"I look back on my career and cherish it," says Leonard. "When you're there doing it, you don't really appreciate it as much as you do when you get older. Sitting back and looking at it now—my achievements, the fights I've had and where I am in my life—it's gratifying. It's good stuff. Real good stuff."

These days, Leonard remains close to boxing. He uses the sport as a metaphor during his motivational speeches and he serves as the host and boxing mentor of the reality television series, "The Contender." The show, which finished its second season in September and lists Sylvester Stallone, Mark Burnett and Jeffrey Katzenberg as executive producers, pits 16 professional boxers against one another for a shot at stardom. "The intention of the show is to reintroduce boxers to the public," says Leonard, "to create superstars and to bring [the sport of boxing] back to where it used to be."

Leonard maintains the show does a lot more, that it is an extension of his legacy as a fighter, which reaches a new generation of fight fans, and that it is also "a breath of fresh air for boxing to position [the sport] in a positive light."

"Fight fans are getting good clean action and no controversy," he continues. "They are getting a great display of talent and a chance to see 16 incredible young men give their blood, sweat and tears."

It's also a jab in the face of boxing today. "The show is humanizing the sport," Leonard says. "They aren't thugs. They are 16 young men who are trying—through boxing—to make a life for themselves and their family and loved ones." The fighters are also offered the representation of SRL Boxing, Leonard's promotion company. In a sport notorious for promoters who line their pockets, oblivious to the interests and well-being of their fighters, Leonard is a strong believer in supporting a fighter's career, rather than taking advantage of it.

"Boxing is a business," he says, "but there are ways to improve it. There has to be stricter rules and regulations and stronger sanctioning bodies, and a pension plan for boxers, which I think is long overdue. There are a lot of ways to help boxing, and I think 'The Contender' is one of them."

When Leonard is away from the ring, he spends time on the golf course. It's the place where he enjoys his cigars most. "I play 18 lousy holes and then I smoke a great cigar," he says, laughing.

Leonard enjoys a wide variety of smokes, including Fuente Fuente OpusX and Cuban cigars. "It's all about camaraderie for me," he says, listing his friends, brothers and sons, Ray Jr. and Jarrell, as regular smoking buddies. "It has to do with my boys and hanging out." But there's also a more personal side to smoking a cigar. "I start reminiscing about life and how wonderful things are," he says. "Cigars let me take in life and digest it."

So what does the future hold in store for Sugar Ray Leonard?

"Where I am in my life right now, there's something bigger and better," he says, puffing on an OpusX. "I just feel like I'm going to accomplish something outside of sports that affects people in a good way. What that is, I don't know, but the man upstairs will tell me."

No matter what it is, if Leonard takes the same approach that he's taken in life, both in and out of boxing, there's little doubt he'll be champion once again.