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Top 6 Boxers That Have Lost Huge Money to Gambling

The gambling industry is a very popular one in the UK and other western countries, and people from all strata of life engage in it. Many people enjoy amazing wins at land based and  Nektan casinos and they roll out huge bonuses to lure in new players and retain old ones. The aforementioned factors have been the talking point and motivating factor for most players.

The fact that a player can now pocket millions through progressive jackpots in a common slot machine is a development that came with the 21st century. However, there have always been huge losses in these casinos by players.

Because it is always nice to balance the narrative, here’s a review of the six boxers that have lost the biggest amount of money while gambling, and in some cases, how they fought their way back.

  1. Ted Cheeseman

We are kick starting this off by chronicling the ordeals of this famous Bermondsey boxer who came out to reveal that he has lost close to £1m in gambling. This Millwall FC fan was not able to give the exact amount he threw away in gambling. But he was serious enough to say that it involves some silly money, which may be in the region of hundreds of thousands, if not up to a million.

The 23 year old welterweight champion from Britain was very popular and one of the Sky Sports favourites. He posited that he became so engrossed in gambling because he made a lot of money within a short period of time. The amount was so huge that he felt nothing spending up to £5,000 per night.

Now, while he never wanted to reveal this to anybody, his partner was aware of the situation all along. He posited that it all started when he was 18. At that time, he was always hanging around people who were much older than him and they all earned huge money then. He learnt the lavish lifestyle and had it in his subconscious. Once he started earning big money like them, he took to gambling just like them.

From Ted Cheeseman’s very own mouth, he admitted to being afraid that by the time he retires from boxing, he may end up a poor man if he does not solve his gambling addiction problem. But help came his way when he revealed the entire situation to his trainer named Tony Sims following the Garcia reverse. Since then, he has never gambled.

He will always remember the good feeling that comes with a winning, and the very bad feeling that follows a heavy loss. However, he also talked about the great feeling that comes when you are embarking on a revenge mission in the bid to recover what you’ve lost. These are the gambling experiences he won’t forget easily.

After recovering from addiction, he still talks about moments when he feels like going back to recover what he lost to gambling and the temptations that come with it. However, he has been able to overcome that urge and to remain sober for a very long time.

  1. Mike Tyson

Now, while Mike Tyson has failed to reveal the amount of money he has gambled away, we know he enjoys spending a lot of money on crazy bets. Of course, the name Mike Tyson is a household name when it comes to heavyweight boxing and his aggressive style gave him titles that made him very famous in boxing and gambling as well.

He spends most of the huge money he wins in boxing on gambling at the casinos. During his career, Mike earned up to $300 million, and a huge chunk of this went into gambling and bets, most of which he lost.

  1. Floyd Mayweather Jr.

This is one boxer that his public display of wealth is well documented. In his Instagram and YouTube pages, you will always see him lineup wads of cash on a table and pose with them, or showcasing his array of luxurious cars in his garage. Apart from his boxing exploits which spans through many years, making him very popular all over the world, he is also into heavy gambling.

At some point, he almost wagered up to $400,000 on a casino game. This will let you understand how he loves gambling. Apart from casinos, he also takes his gambling to sporting events like basketball, football, and even boxing which he takes part in. Mayweather is so involved in gambling that he can spend between $25,000 and $400,000 on a single bet. He even bets on himself to win boxing matches.

While Mayweather has lost some bets, he has also won many. The exact amount of money he has lost to bets is still under speculation because he has refused to reveal it. However, rumour has it that it’s up to $50 million. He has won huge amounts of money on gambling too, taking home $827,272.73 from a bet of $350,000 at one point. Because he is a huge bettor, he is either losing huge amounts or winning a mouth-watering amount. The biggest he has won is the $3 million that he took home when he gambled on the outcome of a college football game.

  1. Manny Pacquiao

Manny Pacquiao of the Philippines is also a heavy gambler. This man, who is now a born again Christian used to enjoy a huge time at the sportsbooks. In one of his interviews, he openly revealed that his fame got to him at some time, and he took to drinking, womanizing and gambling. The boxer, who inspires a lot of people, had night trips to Las Vegas, where he wasted thousands of dollars.

To experience it all, he has also explored gambling in poker tables in Macau and Australia. At some point, Manny wagered a whopping $50,000 on cockfighting. But this is not the biggest he ever staked. That would be the $360,000 wagered on a cockfighting exercise that took place in his native country.

The good thing about him now is that with the help of his wife and support from his family, he has now become sober and does not engage in such wasteful exercises again.

  1. David Allen

Many people sympathized with David Allen when he talked about the gambling frustrations that made him contemplate suicide. This 24 year old fighter from Doncaster gambled heavily. The unimaginable was that at some point, he became so poor, and had to live in an unkempt shed in a garden because of gambling.

This boxer that was exposed to gambling right from when he was 8 years told a story about when he had to stay indoors for six weeks with the same cloth. He even tried to end it all because he lost a bet. He could not get into any boxing competition because of a contract problem that lasted for 15 months, and this got him broke. So, he had to settle some gambling debts by getting into very risky fights.

But he quit gambling, overcame the addiction, and remained sober after meeting with Amir Khan and Brendan Ingle who later coached him and guided him to win the National Amateur Championship.

  1. Evander Holyfield

This world heavyweight champion, who also made history in many ways also engaged in heavy gambling. The revelation is that a total of €150 million was lost by the legendary boxer through gambling and divorce proceedings. He engages in boxing, football, and basketball betting. Because of the amount of money he lost in gambling and three different divorce cases, he has faced bankruptcy on many occasions.

Gambling could be one of the most unpredictable things out there – more unpredictable than boxing. This should not be lost on you as a casino enthusiast. That is why you must stick to responsible gambling in both land based and online casinos.


Integral part of the Irish boxing community for over 13 years