Here’s a Tuesday morning experiment.

First, think of all the boxers you’ve ever heard of or seen. Next, narrow that group to the ones with whom you’ve discussed oxygen absorption, Jimmy Buffett and/or real estate development.

And finally, pare that list down to anyone who’s knocked down Ray Leonard in a fight.

Here’s a wild guess… only Donny Lalonde remains.

The golden-haired Canadian came oh so close to summiting Sugar mountain when he and the future Hall of Famer got together in Las Vegas in 1988 – dropping him with a thudding right hand in Round 4 and wobbling him again in the ninth before succumbing later that same round to a signature Leonard rally.

HBO judge Harold Lederman had Lalonde ahead at the time of the stoppage.

And if you think the conquered champion, now 60, has forgotten it… think again.

“I felt that I should have knocked out the smaller, older, former great fighter. I have lamented about this loss more than anything else I have ever lamented,” he told Boxing Scene.

“Because I should have, not for any other reason. It is the same for any fight or thing in my life that I let get away. I let it out of my hands.

“That I have a hard time living with.”

Nevertheless, when it comes to living, the former Winnipeg resident has managed quite a bit.

He ditched the Canadian chill for Caribbean warmth following retirement from the ring in 2003 – his last fight was a 10-round decision loss to Virgil Hill that July – and he’s since ridden high and been laid low by the changing tides of business, leaving him philosophical enough to channel the likes of Bob Dylan.

Dylan, incidentally, spent time in Lalonde’s dressing room before the Leonard fight.

“Financially we are not real healthy these days,” he said. “A Dylan line speaks to it best, "Seen better times, but who has not?" We own assets we have earned, bought, partially developed, etc. in Costa Rica. We should be OK, but today, with this coronavirus, what world we have after the dust settles, where do we fit into it, how do we get by financially until we know what is next?

“Those are questions I think many of us are asking ourselves these days.”

Boxing Scene caught up with Lalonde to discuss his career’s high and low points, along with his financial ups and downs and his lingering connections to the sport that made him famous.

BoxingScene.com: First off, I know you recently celebrated a milestone birthday. Congrats on that. How are you feeling these days? All good health-wise at 60?

Donny Lalonde: Thank you. Yes, it is surreal. I don't feel any different than I did at say, 40, and for me to see it and hear it, I find it impossible to comprehend. I feel great physically and wish I could still fight, though a couple injuries I had in my career and my age makes it not logical, obviously. Plus, when I train, I feel great but when I spar after a couple rounds, I feel closer to my age.

BoxingScene.com: So, for a kid from Winnipeg it certainly seems like you've led a world-traveler type of life since your fighting days ended. What was it that spurred you to live abroad and so far away from home? A sense of adventure? Warmer weather? Circumstance? Something else?

Lalonde: I was actually born in Kitchener, Ontario, but at 3 we moved to Vancouver and at 14 to Winnipeg. I miss Winnipeg a lot. I often think about living there still. I would have to say the weather and desire to give our family an opportunity to live in warmer weather and, honestly, I have always loved warm places. My wife is from Tennessee so the degree of cold in Winnipeg was a lot for her and the kids after they started their lives on Vancouver Island. That being said, we all really enjoyed our time in Winnipeg. We lived in Winnipeg most of the time between late 2000 ‘til mid-2003.
 
BoxingScene.com: You're in Costa Rica these days. What's life like for you down there? Is it a remarkable change from Canada? What made that the place you wanted to end up, as opposed to anywhere else you could have been?

Lalonde: In my teens I wanted to live in Mexico, likely due to listening to Jimmy Buffett music. In my 20s, the Dominican Republic after having visited and embracing the Island life. At 30 I went to Costa Rica with my new fiance, now my wife of almost 29 years. I have always liked the southern Caribbean lifestyle. At our first trip to CR I was ready to move there. We bought 20 acres of prime rain forest, to donate, not use, but to offset the oxygen absorption of our family. Christi said, “You are not Tarzan, I am not Jane, we are not raising our kids in the jungle.” It took me eight years, but we started living there in ‘98. I was ready to live in the tropics since a young age.

When I retired from boxing in a position to live anywhere I wanted, how I wanted, I moved to Vancouver Island. When I got married to an American girl, we stayed on Vancouver Island. I had friends there from Winnipeg, actually. I invested all the money I made in boxing into real estate in BC, which was an effort to help friends and family get a leg up in life through developing and building, which was our background. What I did understand is people were coming to BC, as they are now as our population ages, so I thought this was a good plan.

But when my accountant in NYC told me I may make money in real estate and my friends and family may benefit from it, but unless we have experience managing money statistically what happens is people get in over their head, cycles happen in business and in the downturns you, your family and your friends are likely to lose what they gain being they do not have financial money management skills. He is 100 percent correct.

Within 10 years me, some friends and family lived very well but in the late ‘90s there was an economic crisis and the ones ill-prepared, including myself, lost everything. It would have been very smart to do what he suggested next. Go do your real estate in Canada but leave me a million or so to manage for you so you have something to fall back on and for your later years. I put it all and lost it all in real estate.

BoxingScene.com: Are the people around you down there aware of your fame as a boxer, or are you just another person in the community?

Lalonde: Boxing has an incredible reach. Since I retired from boxing, all the years since, it takes moments it seems, before someone knows of me from boxing. Anywhere in the world.

Unfortunately, the defamation media effort some people did on me regarding the financial crisis, whereby many of us lost a lot of money and/or now own land we can't do anything with really, has spun the recognition to a negative place which is tragically sad to me. I used the moment I had of fame to help kids and I wanted to be able to help kids my whole life, but that slanderous media people believe to be true – as non-true as it is – has damaged me tremendously. I was very much embraced here and everywhere when people knew of what I did do in life, and I am shunned by people who think I am the person they read about from lies and non-truths spoke about me.

It is a crazy experience, like a bad movie.

BoxingScene.com: When most people think of living in Costa Rica, I'm guessing they think it's a life of endless sunshine and beaches. Just paradise. How realistic is that? Do you consider it paradise for a 60-year-old?

Lalonde: If heat, sunshine, beaches and life in a third-world country is paradise, it can be that. It can also be hell-i-dise in the sense that life here is not easy. It is a different language, we are strangers/invaders of their lands, we are seen as an opportunity to make money. The culture is very different than ours, for example theft is not illegal here under $400 a day. So, theft is in the culture here is acceptable. If you have lots and I have little – if I need a bit to get by and I take your phone, or money from your wallet, for example – that is acceptable here. Certain things are very different, and life is not easy here in ways, but that can be said about anywhere.

If I had the economic wherewithal to just live life and enjoy the weather and nature here, it would be one thing, but we have to survive here like everyone else and that is not easy anywhere. But it is warm.

Now, as for life away from home/family, again there are pros and cons. Pros are adventure, living in new environments, etc., meeting people from all over, living adventurous, new experiences outside normal life experiences – as opposed to living in a familiar world or with family close by, sharing life experiences with life-long friends like milestones, kids, struggles and successes in a more intimate way. You miss out on a lot of that by leaving your home, so to speak, and in retrospect would I do it again, likely maybe a bit of both but more focus on family and community than friends and experiences.

BoxingScene.com: You obviously had a boxing career that 99.9 percent of pros would envy. When you look back at your time in the ring, what are the memories that come back to you immediately? What moments and situations are the ones that you recall most vividly?

Lalonde: My memories in boxing are very vivid. The most fun thing to me was being in there with
guys trying to take my head off and me out-thinking them or confusing them into falling into something I set them up for. For me it was very much a sport. I never cheated like doing steroids to gain weight or anything like that because for me it was sport. Can the best of me be better than the best of you? Can I beat so and so? Can I overcome this strength of his or weakness of mine?

I loved the whole experience. It was specifically rewarding to beat guys who were, generally speaking, bullies. Mustafa Hamsho comes to mind. Jimmy Gradson. Carlos Tite. Leslie Stewart. I particularly enjoyed those victories mainly because I respected the toughness and skills of the fighters but was able to overcome them through using my mind more than anything else. Showing a Ray Leonard a left hook, him falling for it, me hitting him with it then a right-hand combination late in our fight. Seeing the little tricks guys like Pete Piper from Winnipeg taught me that worked against great fighters, was so much fun. Walking into a fight with seriously damaged right hand or left shoulder or broken arm, or limited vision against an all-time great in Virgil Hill, I loved these challenges. I loved overcoming seemingly insurmountable things in life and in the boxing ring.

BoxingScene.com: Did you accomplish everything you wanted to in the ring? Do you look back with pride, or is there regret anywhere?

Lalonde: My three goals in boxing were 1) become world champion, 2) become independently wealthy from boxing so I could retire after my career, 3) hope to meet the girl of my dreams through the sport since I didn't have the self-confidence to think it could happen unless I accomplished something like becoming a world champion. I achieved the three of them by 1988.

I kept fighting because in retrospect it was just too much fun to stop doing. I was capable and I continued to enjoy it, so I kept doing it. Regrets, in boxing, none except I should have tried harder to stop Ray Leonard. I was too patient in the fight and I think it cost me in the end.

BoxingScene.com: I'm guessing most fans know you for the Leonard fight, which obviously didn't go your way. I've talked to other fighters -- like Tommy Hearns, for example -- who tend to get remembered as much or more for their losses as for their many wins. Is that frustrating to you at all? Is there a fight of yours that you wish people would be quicker to recall?

Lalonde: Of course, winning the WBC world championship was the biggest victory of my career. It would be very nice for me for people to have seen or remember that one more than when I lost it. The Leonard fight was a great fight. It had a big impact on the boxing world and for the kids I was working to create awareness for, the same ones that today there is so much exposure about. Those being abused. The fact people remember the Leonard fight in many cases spoken to me also ties with the message at the time about the child abuse awareness campaign I started, so I am very grateful for that fight and that people remember it.

BoxingScene.com: Take me back to 1987, the Eddie Davis fight. You stop him in two rounds to win your world championship. What do you recall about that night, about how you felt in between the first and second rounds -- knowing you had him on the verge of a KO -- and what was the feeling the instant you realized you were a world champion?

Lalonde: Between rounds I was very excited but too focused to really enjoy that feeling. My plan was always to win by knockout since I had a bad decision in my first loss, in my fifth fight. Davis was known for, if nothing else, his durability, caginess and fighting through a way to win/survive in tough fights. I didn't want to make the mistake of doing too much and burning myself out, but I was such a powerful puncher and had the confidence if I connected the fight would end so I was just excited to get out there and try to finish him.

In realizing I had accomplished my dream, well, you can see it in the world's worst victory dance that I did after the fight. I was beside myself, out of mind or out of body, however one says it, it was an extremely exciting, fulfilling and most of all rewarding experience. You have to remember I am a kid whose father did not show him love or give him attention. I had low self-esteem from this. I was shunned by the boxing community and had a do-it-on-my-own type thing even in my hometown. The promoters and boxing people in Winnipeg didn't have me under their control, which they want, so I didn't have their support, the boxing commission’s support, the media was hard for me to win over – mainly because I didn't have an amateur background really and no marquee to my being from any status or scene in the city.

Only two sports writers from Canada were at my title-winning fight. First fighter in 70 years and only the second ever to win a very respected title in sports, and only two Canadian media people in Trinidad for it? The two, Rick Frazier from Toronto Star and Tom Brennon from the Winnipeg Sun, they paid their own way because either the media didn't have any faith in me, or they didn't see the outcome as important enough to cover. It was extremely satisfying to me to accomplish my goals in spite of media not supporting me and in spite of my numerous injuries.

BoxingScene.com: You beat two solid 175-pounders -- Davis and Leslie Stewart -- to become and to stay champion. Do you think people give you enough credit for reaching that level and for beating that caliber of fighter? Did you think you were the best in the world at light heavyweight?

Lalonde: I can't really say much about what people think of me as a fighter. Everyone has an opinion and they have that right. I don't think people today even understand the level of fighters at that time. Those were huge victories for me and set me up to be in line for the shot at the title. After defeating Stewart, I felt very satisfied I had beat a world champion-level fighter and it validated my place as champion. Especially being he beat Marvin Johnson; whose career was very relevant to me for a number of reasons.

BoxingScene.com: Of course, as we mentioned earlier, the Leonard fight was a memorable night as well. What comes back to you about that night? Is it a memory that you think about a lot, or does that one take a back seat to the more successful nights? Tell me something people don't know about that fight?

Lalonde: The special things to me about that night are Bob Dylan in my dressing room and being there for me. My family experiencing such a huge event with their family member being part of. Fulfilling my life-long dream of becoming financially independent after the early days of our life. I was quite sure I had just met the girl of my dreams three weeks before the fight and I was very excited to get on with life after the fight.

BoxingScene.com: I know you fought 13 more times after the Leonard fight. What are the recollections about the tail end of your career? Did you think you'd get back to a championship level again? Were you surprised you didn't? Or were you thinking you'd already reached your peak?

Lalonde: I felt I could get back there. I was very close before fighting Hill. I injured my eye in sparring a week before the fight. Freddie Roach was very confident I was fighting really well and had potential to do very well. I was trying to get and felt confident I could get back, but the injury ended that and all I had in the Hill fight was a puncher’s chance and against an all-time great champion, that was slight. I fought because I loved it. Still would love to.

BoxingScene.com: There's a fair bit of information out there about some issues that you've faced since you last fought in 2003. Again, tell me some things about the business stories out there that the people don't know. What have those articles gotten wrong, and what was your role in those events?

Lalonde: Oh boy, this is a big one. I went into real estate development after boxing. I did it mainly to bring along friends and family into my new world of having money beyond food to mouth. I did very well in Canada, so well in fact that many people around me were very jealous. I had my best man try to sabotage my wedding, my oldest brother tell Revenue Canada I cheated on my taxes, not an ounce of truth to it. I had so much money at the time I had no idea one could ever need money again and I was very clear to my bookkeeper and accountants that any decision is way inside the lines as I never want problems with the tax man. I had my father cheat me out of lots of money, people I thought of as best friends spread rumors so far-fetched and untrue. They have incredible imaginations and should write movies instead of telling lies about people. There is so much more reward in that.

I made mistakes in Canada in spite of making a ton of money in the game. I tried to bring others along as I mentioned. The road to hell is paved with good intentions. Don not forget that. No good deed goes unpunished. Do not forget that. These are sayings I was aware of before walking right into doing the same thing.

When we had a financial downturn in Canada in the late ‘90s I was caught with financial exposure with loans, doing more development than I should have been doing under the circumstances. My mistake, 100 percent. At the same time, Revenue Canada decided to do a five-year audit on me. They froze my assets, 100 percent. They froze my bank accounts and my assets. I had no idea that was legal or possible. I had no idea I had any issues regarding taxation due to the position I took every year when we filed taxes. My bookkeeper says the accountants screwed me over. I think it was just an overaggressive, unethical Revenue Canada act personally. They are known to do things like this worldwide as I have spoken to many with similar experiences.

In Costa Rica, after five years of fighting Rev Can, I finally succumbed to their aggression and after five years of them screwing up my financial life, I had no choice but to start all over again. You asked earlier why CR. Well, if you started with $5 from your sister’s piggy bank at 15 by hitchhiking in minus-30 to get a start in life, and made millions after a long career with many career-ending injuries, then became a multi-millionaire and your own government stole it from you, would you start all over in the same country? I couldn't, so I started in what I hoped would be a more fair-governed country.

In Costa Rica, we started slowly trying to get our senses back. I had a wife, two kids, and we had lived well before this. We lived in a hut with four bunkbeds, no clothes washer or even a clothesline. Christi dried our laundry on a barbed wire fence. We didn't have a car. We had no means of earning money in a foreign country and neither of us spoke the language. I told Christi I wanted to run the beach, meditate, do yoga every day for a month to find a new direction in life. We did that. On the 30th day, I had a clear vision, which was that if I would build an opportunity it looked to me like a pie at the time. The message was make a big pie, take your share, make lots for others. At the time in CR, real estate was very inexpensive. There were newly developing industries here in a number of areas and it seemed like growth from North America was coming, so it made sense to do what I knew, real estate.

I started a real estate company funded by the guy who basically started and owned the majority of Tamarindo, the town we lived in at the time. We did very well. Slowly made money to buy a couple of lots, build a home etc. I left to CR after the Hill fight in July 2003. I was still fighting bankruptcy in Canada but decided my life was no longer going to be there. After the Hill fight in 2003, when we got to CR, we did what we could do, but honestly, we were in shock at the state of our life and I wasn't so productive at that point. After a while, after painting houses to pay rent, after doing a few small business deals buying a lot for $4000 and selling for $6000 type thing, I started to get my confidence and sanity back.

It was about mid-2004 we started the company. I did not own it, I ran it and the owner trusted me to do so, along with another friend who was Canadian, a female, a mutual friend – she had many years‘ experience in the business so together we represented his products and those of others. We did very well all in all and over the next six months to a year started to get our heads into a market that suddenly started to grow exponentially.

I saw some great opportunities and jumped in not only as a person selling real estate for Russ but also looking to find parcels I could cut into slices and share the pie with others that would then provide land if no other benefit to me. Keep my share. The market grew fast. The demand grew equally as fast and before we knew it we were in a hot market and people were literally flying into our office to buy, invest and or just jump on the gold rush of CR real estate.

My friend who I ran the company for was running out of inventory, he had to sell as infrastructure was much slower than demand. We learned that was normal in CR but only after some hard lessons. Myself, an old friend from Winnipeg and a young guy out of the U.S. started a couple of projects. They felt they had a group of investors they thought they could bring into the projects. Through my work with Russ I was entrenched in the business and many I knew were interested to look at longer-term investments that we would develop ourselves and we started these projects.

These, much bigger projects, one a 400-acre project that was to become a Western style town and the other a 1,000-acre property with gorgeous ocean views we saw as another very different ocean view community. The idea was we pre-sold lots that were to be serviced with gravel road, water and electrical.

At a certain point, a group within the investors decided they preferred if we did gated communities. This required a lot more money than we raised and a lot more procedures and protocols/risk. My wife took a course and studied the laws of the country and strongly advised us to not change our objectives but the ego and greed of men, myself included, resisted her logic and we voted to change the direction of the projects. Foolishly, I sided with them, we have all lived with that mistake only too infamously.

We started raising money again because of the change, the work I had done and money spent to date was irrelevant, as we were doing a different style community that required paved roads, gated entrances and boundaries, underground electrical, phone, cable, internet, etc., a golf course on one project and many other amenities. Completely changed the projects to a place I was not educated to run so I stepped aside and hired a CFO, project manager, project oversight guy, accountant, etc., etc. A couple million and a couple years into that stage of planning, road building etc., we hit the financial crisis and the rest is history. Brokers of investors, friends, investors, they started an extortion effort to get me to give them land so they could sell it and live through the downturn. I did not give in to their extortion, so they threatened me with and eventually accomplished a defamation effort.

They connected with the poor level of media types that are writing for the ICIJ, a group that stole records of a law firm in Costa Rica that was working with George Soros or other scum types that were working to exploit people that use off-shore entities to hide or otherwise place money where they save on taxes or for other reasons.

I had used these same lawyers to set things up for our investments in CR and was advised to do so by my lawyer who I met through the former president of the country’s family. It was suggested to me this was the best way to set up in CR for tax-planning purposes, asset protection and privacy. Having experienced what I did with Rev Can, I was easy to convince of this one.

When the media types met the defamation/slander/extortion group, it was a perfect storm to spread the lies. That they did a great job of.

BoxingScene.com: How are things for you and your family financially these days? Have all the major issues cleared up? Do you still have a regular job or are you able to live off of the money you made previously?

Lalonde: I certainly have no pension, no real liquidity. I have assets but assets with obligations are liabilities until they are assets. So it is a trying time but I started with nothing at 15, I have weathered a lot of storms in my life and I plan to work through this one and come out in better shape than ever by the time we get past all this. Maybe I will still retire at 65. That would be a miracle, but I am not a quitter and I plan to have financial peace of mind again in life and I am confident we will get there.

BoxingScene.com: What is your connection with boxing now? I understand you've trained some fighters in the years since your retirement. Are you still connected in any way? Do you want to be? Or are you completely through with it now?

Lalonde: I love boxing. I would rather be involved in boxing than anything else. I trained fighters. I have managed a few, recently in Malta where we lived for three years. Boxing is a big money game. If you have big money you can play in it, or if you are funded by someone with big money you can make a living in it. Short of that, one needs to have a secondary way to make a living if you’re going to be involved in it. I spent a few years in Malta helping fighters, investing in them, training them and managing them. None of it worked out to bring back money but I am still very happy to have tried to help some fighters and I want to do it a lot more. I would love to share what I have in the bank from boxing, knowledge wise.

Life is an adventure and my adventure is not over. I want to clean up things regarding real estate and my name, spend time with my family and help as many fighters and kids as I possibly can still in life. I am only 60, so much time left, so many more to help, share with and watch live their dreams like I did.

* * * * * * * * * *

This week’s title-fight schedule:

No title fights scheduled.

Last week's picks: None
2020 picks record: 14-3 (82.3 percent)
Overall picks record: 1,130-368 (75.4 percent)

NOTE: Fights previewed are only those involving a sanctioning body's full-fledged title-holder – no interim, diamond, silver, etc. Fights for WBA "world championships" are only included if no "super champion" exists in the weight class.

Lyle Fitzsimmons has covered professional boxing since 1995 and written a weekly column for Boxing Scene since 2008. He is a full voting member of the Boxing Writers Association of America. Reach him at fitzbitz@msn.com or follow him on Twitter – @fitzbitz.