Wealthsimple is an investing service that uses technology to put your money to work like the world’s smartest investors. In “Money Diaries,” we feature interesting people telling their financial life stories in their own words.

As a kid, money to me was something that was free, because it came from my parents. I looked upon it as something to use to buy my favourite stuff: cowboys and Indians toys, roller skates, comic books, things of that nature. Those things that I Loved with a capital L. And my mom and dad always had that dollar or that fifty cents to buy that thing. Especially ice cream cones. They were my favorite.

Everyone was poor in my neighbourhood, so I never knew. I never knew the difference. Everyone was poor, so it was just average that you didn’t get everything you want. In my book, it was a great life. Then when I was eight, nine, ten — I had three older brothers so there was six of us in the house — I realized that money was a factor. Naturally my parents never talked about money but I’d look at their facial expressions when the rent was due. I felt there was a correlation, there was a connection, with putting a smile on your face and not having a smile on your face – it was always when my parents didn’t have enough money.

Every year that went by, I understood a lot more. They were absolutely struggling. I’m sure they were earning under a hundred dollars a week. My father, Cicero, who passed away last year at 95, he had a fifth or sixth grade education, but he was a hard worker, so he got a job at S&R supermarket in Washington D.C. He was considered a night manager, whatever the hell that meant. He went to work late at night and came back in the afternoon, worked crazy hours. They wouldn’t allow you to work that long now. But he was always on time and a couple of times a week he would drive the trash truck to dump the trash for extra money. My father was a simple man, and it didn’t take much to put a smile on his face. He just made sure there was food on the table. Somehow, some way, my parents always made sure we had dinner. Dinner and breakfast, but breakfast was cereal — Cheerios or Cornflakes or whatever. We had two meals that were practically guaranteed. They made sure they supplied that.

My mom was a licensed practical nurse. She worked in a hospital and she worked crazy hours, too. Not like my dad, but she worked hard. She’d dropped out of school in the twelfth grade, so she was just a little more advanced than Pops. But they both were hard working parents. Never complained.

I lived in Washington D.C. on L street and I used to walk with some of my friends to the Washington Monument, which was probably a 40 minute walk. And I saw these beautiful homes, beautiful apartments. I saw different neighborhoods, I saw different people dress impeccably, I saw these donut shops, these coffee shops, these restaurants. I just saw there was another world. And I said, ‘We’re so different, we’re so different’. I never complained about it, I just accepted what we had.

But as I got older, being exposed to it, I think naturally I wanted to have more. I wanted to have that big home, have that clean place for my ma and for my dad. I really wanted, before they left this earth, for them to have something — a home.  And naturally, I wanted a car. A nice-looking car. Always. I saw my father drove Chevrolets and Fords, so anything by Chevrolet or Ford, I wanted one. I didn’t care how old it was. I wanted one of those things, those vehicles.

One time, walking to the Washington monument, I walked into this little club of some sort, because I had to go to the bathroom. I remember this like it was yesterday. I walked in there, and some guy, some white guy, said, “What are you doing in here, nigger? Get out of here, nigger.” And I’d never heard that. I looked at him and I ran out. I’d never experienced such a volatile anger. I was also a very quiet and shy kid. So I wasn’t exposed to that reality.

When I got home, I said, “Mom, this man called me a nigger, told me to get out.” She said, “don’t worry bout it, son, don’t worry.” She did not explain to me about how society was at that time. She said, “Ray, so. Don’t worry bout it.” And what that meant was: just keep it quiet, keep it to yourself, don’t say anything. I just let it go. It’s funny, I just accepted it. I guess that was her way of protecting me.

I was meant for boxing and boxing was meant for me. I put gloves on and it was like wow, we found each other. I was very shy and quiet, but boxing and me, we connected. It was something that resonated with me. My kids, when they see me on TV, or on old films, and they look at me and they look at the film, they say, “That’s not papa.” They call me “Papa.” They can’t believe that their father, their papa, was a boxer, was a fighter. Because I’m so the opposite: I’m not confrontational, I’m somewhat quiet, soft-spoken and what have you. And in the ring I was so dominant. I sometimes, say: who is that guy? Because I could hit that switch. You know, we all have that fighter side of us. We have that thing, that last fight, that big fight inside of us.

When I came home from the 1976 Olympics, after I won a gold medal, I had no job. I had no ambition of turning professional. My knuckles were really breaking down. Boxing itself is a tough sport, but when you have kind of a handicap or problems with your hands, or whatever part of your body, it’s not fun. And I just thought that would be it for me. Everyone kept saying, “You gonna turn pro? You gonna turn pro?” I said, “No, I’m not turning pro, I’m going to college. I’m going to the University of Maryland because I’ve got a scholarship to go to college, to further my education, get a good job, and take care of myself and my parents.” That was my dream.

That dream was cut short because my dad, after the Olympics, went into a coma, and he was about to leave us. The doctor said, “you know, your father’s lucky but I don’t know how much time he has.” I’m looking around and saying, “hey, how can I make fast money?” And I asked that of my mentor, Janks Morton (the activist and filmmaker). I said, “Janks, how do I make fast money?” He said, “Turn pro.” I didn’t give it a second thought. I turned pro for that reason only: to make some money to pay my father’s hospital bill.

Mohammed Ali gave me about half an hour or so, talking, advice. I was at the 5th Street Gym in Miami, training. He said to me, “Ray, don’t let anyone own you. Make sure you sign your own checks. Always stay in shape.” The way he said it, it was like he was my big brother. And I heeded his advice.

I was a lucky man that Janks Morton introduced me to Mike Trainer, who became my lawyer and my business partner and my dear friend. He took care of me. If it wasn’t for him, I wouldn’t be in the position that I am today. He made sure that I got what I deserved. And he worked with me from a business perspective. He said, “I don’t know anything about boxing, but I do know business.”

From 30 people he borrowed a thousand dollars each that went to me. It allowed me to box and train and work out. [The investors in the corporation Trainer formed agreed to receive 8% interest and no equity or further rights in Leonard’s career.] And my first professional fight I made between, I want to say, 40 and 50 thousand dollars, which was unprecedented back then, for six rounds. I paid them off, became incorporated, and promoted myself. Back then it was unprecedented: free agents. But I didn’t want to be one of those guys who were taken advantage of by some of those other guys. And then from there we went to Wall Street, we did the endorsements, and all those things started coming my way.

Two years later in 1979 I was making a million dollars, fighting Wilfred Benitez. I bought my mom and dad — I’m almost crying right now — their first house, handed them the keys, walked them into the house with their eyes closed. That was one of the biggest moments of my life. I said: “Another thing, neither one of you have to ever work another day in your life.” I told them that. I’ve never seen so many tears in my life. Sometimes I relive that moment – that moment in time that I saw the expressions of my parents.

I got myself an apartment at the time, but their house was the biggest investment that I made. Then, as a couple of years went by, I bought myself a house, got married, all those things came into play because I could afford it. Like cars. When I started making money, especially with my first million-dollar fight, they said, “Ray, you should buy a Roll’s Royce.” I mean, I didn’t care about these cars. I didn’t like those cars. Although I did have them. I think with one of them it was at one of my retirements — because I retired a lot of times — I think I was bored and I just bought it. But when I turned them in — this will give you some perspective on how much I didn’t love these cars — the Bentleys and the Corniches, they had maybe 2000 miles on them.

I rode around in what I liked. What Ray Leonard liked. I used to have a 1964 Chevy Nova, and the cars I did like were the Volkswagen and a Toyota 280z. I loved those cars.

When people tell you, “You made a million dollars!” you’re introduced to so many things. For me, it was alcohol, it was drugs, it was just so much. Now I had more friends who were not friends. All of a sudden I started becoming sad, because I didn’t know who was who. It’s hard to distinguish who really likes you because you’re Ray Leonard, or because you’re Sugar Ray Leonard. My partner, Mike Trainer, said, “Ray, you’re not going to be happy until you learn how to say no.” And that spoke volumes. Because I thought that when you had money, everything was happy. No, no, no. If you’re not situated, if your feet are not planted on the ground, you won’t survive. And I thank God I was able to overcome that, I was able to get through that.  

Someone once told me, money is power. And to a degree it is, but if you don’t know how to use it, if you don’t know how to use your money, it’s not power.

I made over a hundred million. I paid taxes, too.

I’m somewhat — well, extremely — conservative. Instead of just going into stocks big time, I kind of diversified – municipal bonds and things like that. I was a student of Mike Trainer – he taught me and educated me so much. Naturally, early on I didn’t listen to it, but as we became closer, and developed trust, and what have you, whatever he said I knew was right.

Before I turned pro, I got interviewed by a reporter. He said, “Ray, what do you want to be?” I said, “I want to be special.” When I said that, at that moment, I meant it, but couldn’t elaborate. I just didn’t want to be known as a boxer guy who beat people up. I wanted to be known as someone who did that, won the gold medal, and made an impact in the ring, but he also made a huge impact outside of the ring — in philanthropy, and giving people hope, like Mohammed Ali did with me. Maybe because I’m getting older and more settled and everything, I see things in a different way and perspective: I’ve done something. I’ve moved something around. Not only for myself and my family — I took care of my family, my entire family, pretty much, and some of my friends — but it’s like giving hope to others without even knowing you do that. I hear people come to me, and say, “Thank you, man, because your career gave me some strength as far as not quitting, and not giving up, and believing in yourself.”

I’m the kind of guy who has to work. I don’t think I’m ever going to totally retire. I love it all — the motivational speaking, helping people. Back in the day there was a show called The Contender, I loved that show, and now with The Zone, it’s kind of like the Netflix of boxing, of all sports. I do commentating with them. I started a foundation with my wife ten years ago, raising funds for the children’s hospital in Los Angeles for their various programs: a center for endocrinology, and trying to find a way to knock out diabetes.

Am I good with money? When your teenagers call you a cheapskate… they look at me like I’m an old fart, some guy. They don’t see me as someone who just spends money crazily. But I pay my share. Money, it almost is like a fight. You gotta pace yourself. You just can’t go out there and buy everything. It’s like everything’s almost like a crapshoot, but do what works best for you. People have to do what’s best for them. What works for me doesn’t work for everybody else, but what works for me is the fact I work hard for what I want to achieve. I don’t take short cuts. What you see is what you get. I’m in an incredible place in my life, and it’s not by age, it’s about experience. Without question, I’m a really blessed man.

I got four kids, and six grandkids… what do they call that when you say you’re home by yourself? Just you and the wife? Empty nesters, that’s what we’re becoming. So now we’re looking to downsize the house, our lives, simplify everything. I love where I’m living but it’s just too lonely here without my kids. I miss that screaming — you know, that screaming and that fighting and that yelling? I miss all that.

If my dad hadn’t been sick, if that wasn’t the scenario...? I don’t know. Put it this way: the only thing I ever wanted to become, besides a boxer or gold medal winner was — don’t ask me why — a substitute teacher. Not a real teacher — a substitute teacher. I don’t know why! I’ve asked myself that for forty years. I say: why would I want to be a substitute teacher? The ones that I’ve met were always so nice to me, and I wanted to do that myself.

I am very frugal right now. But anything that says “golf” and “lower your handicap by three”, I’ll buy it, no matter how much it costs.


As told to Chris Heath exclusively for Wealthsimple; transcript edited and condensed for clarity. Illustration by Jenny Mörtsell.

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