Harry Simon is 30 years undefeated but still haunted by loss

When Harry Simon won his first amateur bout at 10 years of age, his reward for winning was an orange. Not an orange sash, or an orange rosette, but an actual orange; one he could peel and eat. Harry’s next challenge, in fact, was to try to resist the temptation to eat this orange and take it home, where it could then be showcased like any other trinket a boxer might earn in victory. 

For seven days that orange had pride of place, just not on a mantelpiece but on top of a fridge. It was there, on the fridge, Harry could find it whenever he entered the kitchen looking for a reminder of what he had achieved in the ring. It was also there that the orange would change, both in color and shape, and somehow become the perfect metaphor for Harry Simon’s boxing career and indeed his life. 

Unlike a trophy, you see, the orange on the fridge was forever altering and deteriorating. Even as a token of success, its shelf life was short, indeterminate. One day it was fresh and fine to eat, the next it was rotting, no good. “After two or three days it had changed color,” Simon recalls. “It was going green. I’ll never forget that.” In the end it would wither and die, as expected, yet the memory of it has sustained. So too has the memory of the success the orange represented. “I remember it was a three-rounder or a four-rounder and it was against someone who was 14,” says Simon. “He had been a boxer as an amateur for maybe two or three years. I beat him on points.”

Born in Walvis Bay, Namibia in 1971, Harry Simon was the last of 11 children. He grew up without a father and often found himself surrounded by older boys and girls, the impact of which seems, on reflection, to have been almost as great as having no father figure. 

“I would say I was a naughty boy,” he says. “I was a naughty boy and I would get in trouble a lot. I would always be fighting everywhere. I would fight at school and also when I wasn’t at school.” He then pauses to make room for a greater degree of honesty. “I would say I was a bully,” he now says. “As a child I would bully other children. Some of them were older than me, but I still bullied them. I didn’t have any fear. None at all. I don’t know why that was. I had 10 siblings and I’m the last born – the 11th. It was a difficult childhood for me because I had to grow up without a father. I felt his absence. Every boy needs a father. I was not taught well. If my dad was there, he would teach me not to bully other people. He would teach me to do the right thing. I was not disciplined at all.”

When I speak with Simon, he is in Walvis Bay and has just been to the boxing gym, where he continues to find the solace he requires in adulthood and the discipline he lacked during his childhood. He is now 52 years of age. He will box again on November 2 in an exhibition in Namibia and is still getting from boxing the same things he got from it growing up. It is still, for him, a home away from home and a sanctuary. It still teaches him the lessons and provides him with gifts he didn’t receive as a child. “Boxing gave me discipline, one hundred per cent,” he says. “It is the same for other people in Namibia, too. In Namibia, boxing is very popular. I could be wrong, but I would say it is the number one sport in Namibia. In the gym today I was training with a lot of kids. There may have been 60 kids in the gym.”

He says of his own training: “I don’t feel fit yet but I feel good to get back in the ring. I’ll be ready. I’m training every day except Sunday. I’m doing my roadwork in the morning and then I do boxing in the afternoon. I never thought I would be boxing at this age, no, but I still enjoy it very much.”

For the younger ones, boxing is a way to learn, to find discipline, to find strength. For Simon, on the other hand, one gets the impression that the gym is now, at 52, more akin to a time machine, something he can use in the hope of feeling youthful again. Not only that, boxing, as a discipline, is all he has ever known, with the ring often the safest place for him. “I had over 200 amateur fights,” he says, “and lost maybe two or three or four.”

With this kind of success rate, it stands to reason that Simon associates the ring with progress and, for the most part, happiness. As a pro, it was the boxing ring that brought him money and acclaim and even as an amateur his exploits inside it led to Simon representing Namibia at the 1992 Olympics in Barcelona. 

“For me, I don’t want to lie, that was not a good experience at all,” he recalls. “It was 1992 and they had the computer scoring. Many people could see that this boy won but the computer would say no, this boy lost. It made me angry. You see it all the time in amateur boxing. Just because the boy is from Great Britain or America, and he fought a guy from Zimbabwe or somewhere else in Africa, they say they won even if they didn’t. A lot of superstars have lost at the Olympics because of the scoring. Roy Jones lost against a Korean (Park Si-Hun) in Korea (at the 1988 Olympics). Also, Floyd Mayweather lost (against Serafim Todorov in ’96).”

Like any boxer, Simon, outpointed by Aníbal Acevedo in the first round, wanted a win to feel like a win; just as a loss should feel like a loss. He wanted fights to be decided by his own physical prowess rather than politics or popularity. It was for this reason, among others, he turned professional in 1994.

“I was working at the time in sports and recreation and I had to give that up to become a professional,” he says. “I had to leave my job to go to South Africa because there was no professional boxing in Namibia. It was very difficult. I had to go look for a place to stay. I didn’t know anybody in South Africa. I had to show everybody in the gym how good I was. Everybody was asking, ‘Who is that boy? Who is that boy?’ I had to prove myself in the gym. That’s what happened. As time went on, I enjoyed living there. It became my second home.”

While in South Africa, Simon, known as “The Terminator”, won nine fights and only went the distance once. Then, having boxed on several occasions in Great Britain, he received a shot at the WBO junior middleweight title in 1998. The owner of this belt at the time was Ronald “Winky” Wright, one of the most technically proficient fighters of the modern era and already someone most junior middleweights were eager to avoid. He, too, had impressed in Britain, beating the likes of Ensley Bingham, Steven Foster, and Adrian Dodson, and seemingly had no problem travelling around the world to make money and beat up opponents in hostile territory. The idea of going to South Africa to fight Simon therefore was deemed no more than the continuation of a theme for Wright.

“That was a dangerous fight for me,” recalls Simon. “That one opened my eyes. If I had lost to Winky that night, my life was never going to be the same. I was maybe going to retire after one more fight, or maybe have no more fights. But I fought my heart out against him. If I couldn’t win after fighting my heart out, what would be the point? I gave everything in that fight. I was also a very inexperienced man. I learned a lot from that fight.”

Fighting at a frenetic pace throughout, Simon learned as much about himself as he did Wright that night in Hammanskraal. He had, at the time, only 16 pro fights to his name whereas Wright was 38-1 and accustomed by now to beating world-class challengers on the road. Nevertheless, Simon ultimately came out on top, beating Wright by majority decision, and now joined the same rarified club in which “Winky” himself could be found. Suddenly Simon, Namibia’s first ever world champion, was both a marked man and a man any astute fighter would look to avoid. 

“I love Winky; I love that boy,” he says. “I named my son after him. Winky is not a popular name. It is only known to the people who know Winky Wright. But I have a tattoo of Winky on my arm; I have the names of all my children on my arm.”

Of the two it was of course Wright who would go on to find both fame and the kind of paydays that would forever and for good reason elude Harry Simon. Yet, by virtue of him beating Wright, still Simon remained a feared, dangerous man, his quality plain for all to see. 

After beating Wright, he went on to defend his belt against Kevin Lueshing, whom he stopped in three rounds, Enrique Areco, whom he stopped in 10, and Rodney Jones, with whom Simon went 12 rounds in Canada, retaining the belt the same way it was won: by majority decision. In his next fight he returned to Britain to face Wayne Alexander, a heavy-handed fighter unbeaten in 16 fights. 

“It was a great fight,” Simon remembers. “Before the fight I told everybody that it was going to be my easiest fight. But I didn’t know he had that much courage. He was also the biggest puncher I faced.” He pauses and laughs, perhaps remembering the stoppage in round five. “Still it was an easy fight for me, though.”

It would also be Simon’s last fight as a 154-pound junior middleweight. Afterwards, he would signal his intention to vacate his WBO belt and move up to middleweight, which is where, in 2001, he beat Hacine Cherifi to claim the WBO interim strap and then Armand Krajnc to win the full version of that title the following year. Both those fights went the distance, with Simon taking unanimous decisions, and both would be considered mere afterthoughts given all that was to happen to Simon in 2002. 

In truth, the only names that really matter at this point are the following: Frederick de Winter, a 31-year-old father, Michelle de Clerck, a 29-year-old mother, and Ibe de Winter, a 22-month-old baby. Those are the names of the three Belgians killed by Harry Simon’s Mercedes-Benz ML500 in a head-on collision at Langstrand, just between his birthplace Walvis Bay and Swakopmund, in November of 2002. 

Nothing was ever the same after that. One life had changed, three lives had ended, and yet it wasn’t until August 5, 2005, almost three years after the crash, that Simon was found guilty of culpable homicide and handed a two-year jail sentence. He appealed this decision but to no avail, then started to serve his sentence on July 9, 2007. By that time, he had, he says, lost everything. He had lost the ability to box on account of his injuries – a broken right arm and a broken right leg – and he had lost both his freedom and peace of mind.

“It took me five years to recover,” he says of the injuries, aware that a loss of time is incomparable to the loss experienced by three Belgians visiting a Namibian beach resort one day in November. “It was up and down. I had to go to America for surgery, go to London for surgery, come back to South Africa for surgery… it was tough. That whole period was very difficult for me. I just took one day at a time and tried to get through it. I wondered if I would box again and I was worried that would never be possible. I was in my prime at that time in my life and I actually lost everything. I was supposed to fight guys like Felix Trinidad and Bernard Hopkins for big money but that couldn’t happen. Everything I wanted to happen could not happen anymore. I accepted it. I pray a lot and that has helped. I had to go to church. There were a lot of people encouraging me as well. This is life and I have to accept it.”

In total, Simon was out of the ring for five years. These were meant to have been the best and most productive – both athletically and financially speaking – five years of his life, yet still he is lucky; lucky to have rediscovered freedom and a new perspective and lucky to have even been able to box again. 

“That was one of the hardest things I have ever done,” he says, speaking now of jail. “You lose everything and still they put you in jail. It was like being buried alive. That is what it felt like. 

“I was training while I was in jail, so I always hoped to box again. When I came out, I was almost 100 per cent and ready to box. I wanted to be a world champion again.”

While Simon may have fallen short of that, he did continue to box and make some sort of living from the sport in the subsequent years. In November 2018, some 16 years after the crash, he even shared a bill in Namibia with his son, Harry Simon Jnr, a boxer currently 22-0. “That doesn’t happen every day, so it was a very proud moment for me,” he says. “I have 10 children and I am in their lives. That is the most important thing.”

One gets the sense he is forever making up – either for lost time or an absence, be it his own or his father’s. It is why, perhaps, Simon continues to box at 52 and why, even though content with his achievements, there remains an urge on his part to do more. 

“I am proud of what I have achieved in the ring,” he says. “What I have done is something special for me. If you look at my record, it’s 31-0 and I’m 30 years undefeated. Do you know why I’m saying that? Because I’m still active. There’s nobody on this planet who has been undefeated that long. I’m the first to do that and I’m the only one. I don’t know why people don’t mention it. Maybe it’s because I’m from Africa. I look around at all the people and there is nobody else who has done what I have done.”

He adds: “I’m doing many exhibitions in Namibia and South Africa and I want to do an exhibition against (Floyd) Mayweather. Mayweather is also undefeated. I remember he did an exhibition with Jake Paul’s brother (Logan Paul) and Jake Paul’s brother was a cruiserweight. If I can get my weight down, we can do an exhibition. That will be an exhibition between two fighters with a combined 81 fights without a loss. He beat good world champions; I also beat good world champions. So we can do an eight-rounder or a six-rounder. Let’s give the fans a great show: two super world champions who can’t remember how it feels to lose.”

That, of course, is not strictly true. Harry Simon, more than anyone, knows exactly what it means to win and exactly how it feels to lose. He is in fact a man well-versed in the extremities of both winning and losing. He knows now that just as a decaying orange is not an adequate representation of victory, nor does losing a boxing match against another boxer do any sort of justice to the feeling of loss.