Athletes Who Went Completely Broke With Dumb Decisions

Here are some athletes who went broke with dumb decisions!

September 20, 2022・

19 min read

Pro athletes are among some of the highest paid people in the world! Whether it’s slam dunks, touchdowns or home runs -- if you give the crowd something to cheer about, you can cash-in millions! But, with great financial power comes great financial responsibility -- and not all our favorite stars are up to the challenge!

Whether they blew it on golden bathtubs, rock and roll cafes, or contentious divorces, these are the sporting heroes who made some seriously dumb decisions and lost it all!

IRON MIKE’S SPENDING HIKE

For Pro Boxer Mike Tyson, there’s no such thing as bad publicity! Able to turn any attention into showcase fights and publicity endorsements, Iron Mike became one of the highest paid athletes of all time! From his debut in 1985, his total career earnings rack up to a jaw-dropping $423 million – at least!

So, what did he do with that money? Well, he blew his record-breaking fortune on just about anything money could buy. He bought opulent mansions, limousines, parties, clothes, motorbikes and Bengal tigers!

Yes, indeed; Mike Tyson bought three tigers as pets! And they lived right alongside him in his $2.5 million mansion – one of at least 6 he owned!

But keeping tigers as pets is not cheap! Iron Mike coughed up $70,000 for the big cats, with another $200,000 a year going on their food bill alone! Not only that, but Tyson was forced to splash out another $125,000 just for having them house-trained!

It’s unclear if that even worked considering one of the tigers, Kenya, ended up attacking one of Tyson’s neighbors. For that incident, Tyson was forced to foot a $250,000 damages bill! That means – in just the costs we know about – the multi-millionaire spent at least $645,000 on tigers!

Adding in the $173,000 80-carat diamond chain, $65,000 on limousines and $2 million golden bathtub, you can’t be surprised that Tyson was bankrupt by 2003. A man who once bathed in a golden tub and could charge $30 million for one night’s work, was $38.4 million in debt!

At the time of his bankruptcy, Tyson was 37. Only 7 years earlier – for his 30th birthday – the star had splashed more than $435,000 in just one night of partying! Now, approaching 40, all Iron Mike had to show for it were climbing debts and more than $13 million in unpaid tax!

But all was not lost. By 2021, Tyson has at least made some of his fortune back. No one can sniff at his current estimated net worth of $10 million! That’s a lot of money to the rest of us, but, to Tyson, that’s just 2.4% of his original fortune.

DESTRUCTIVE DIEGO

Widely considered the greatest player of his generation, Diego Maradona’s glorious 21-year soccer career saw him rise to god-like status in his native Argentina – and earn some serious bucks!

When he played for the Italian team Napoli between 1984 and 1991, Maradona raked in $3 million a year. On top of that, the star was inundated with sponsorships and endorsements, totaling another $8 – 10 million!

At his peak, Maradona had it all! The star spent lavishly, scooping up 5 properties in Argentina, a $360,000 Rolls Royce, a BMW i8 worth around $175,000, and a diamond ring worth $360,000 to name a few assets!

Later in his life, Maradona was even gifted a large, amphibious tank by the Belarusian government! When you get a free tank, you know you’ve made it! Being paraded on the streets in his new ride, Diego looked like the richest man on earth – but was he?

In 2005, the Italian government revealed that Maradona had all this money because -- he was evading tax! That’s right! While he’d spent at least $895,000 on flashy cars and jewelry, the star owed a whopping $48.6 million in unpaid taxes! During his life, the star had paid off less than $50,000 of what he owed, and two luxury watches.

Despite this, when he sadly passed away in 2020, the Maradona family were expecting a substantial inheritance, with Diego claiming during his final days that he had $100 million in assets. But, when the wake was over and the receipts came in, it was revealed his spending had taken a huge toll!

To their horror, the Maradona family discovered their patriarch had only $500,000 left to his name! That’s not bad, but it’s hardly the millions they were expecting! And, to this day, those debts to the Italian government still need to be paid. It seems not paying all that tax turned out to be super irresponsible.

RESOURCELESS RAGHIB

As the wide receiver for Notre Dame in the early 90s, Raghib Ismail’s star was on the rise. With hype building for a professional career, Ismail wanted to commit to the National Football League in 1991. But then, something unexpected happened.

The Toronto Argonauts – who were from the newly formed Canadian Football league – offered Ismail a whopping $18 million to play in Canada! After success there, he was eventually drafted back into the NFL as a wide receiver for the Oakland Raiders. In career contracts across both leagues, Ismail banked around $26.9 million!

And then he retired in peace, right?! Not Raghib! Instead of settling for a comfortable retirement, the ex-player embarked on a series of business ventures – or, more accurately, business blunders!

There was the pre-paid phone card idea, the calligraphy business, the religious movie and – craziest of all – the Rock and Roll themed café. And no, it wasn’t the famous Hard Rock! Each one failed hard.

Obviously, no one told Ismail that the Rock n Roll café idea might have already been taken. That might explain why – despite his $300,000 investment – Ismail still has no idea whether the restaurant ever materialized or not. Ismail may as well have thrown that $300,000 into the sea!

Now, not all the failures were Ismail’s fault. The Rock and Roll café suffered from chronic mismanagement – a rite of passage for every rock group – and the souvenir shop was wiped out by Hurricane Katrina! But no matter the cause, there was no recovering the lost dollar! And so, Ismail’s fortune was well and truly wasted.

Having lost it all, Ismail was able to avoid total bankruptcy through broadcast punditry. But even then, despite all he’d lost, the guy just couldn’t stop investing! And, if you can believe it, Ismail’s final investment in the mouthguard company Bitetech -- actually paid off!

He may have made some silly mistakes, but Bitetech is still in business! Raghib Ismail may not have all the money he once had, but at least we can say he’s not broke anymore! Which is more than can be said for some others on this list.

DEPLORABLE DYKSTRA

For baseball fans of a certain generation, Lenny Dykstra was the man! A heroic slugger for the New York Mets and Philadelphia Philles, Dykstra was nicknamed “Nails” because of his uncompromising style of play.

That winning attitude meant that by the end of his career in 1996, Nails had earnt an impressive $36 million! Not only that but, after investing in a successful chain of car washes, Dykstra had bumped that up to a whopping $58 million by 2008.

But $58 million just didn’t leave Dykstra satisfied! In search of more dough, he went on to become a stock-picking columnist! Dykstra took at least $250,000 worth of secretly issued stock in exchange for recommending that stock to subscribers of TheStreet, who paid a whopping $1000 a year for his advice.

And the reason that sounds shady is because it is. On top of that, his desire to live large lead him to publish a glossy magazine called the Players Club, the bills of which were not cheap.

Because of all this complex business, Dykstra found himself facing a cascade of lawsuits, outstanding debts, and bills. In those lawsuits, damaging allegations emerged that Dykstra had resorted to using his employee’s credit cards to fund his lavish lifestyle.

On one, he left a $32,000 charge for a leased jet from Atlanta to Montana so he could watch his son’s minor league baseball game. Doesn’t exactly sound like a business expense to me!

As a result, in 2012, Dykstra found himself on the receiving end of charges for both fraud and money laundering! After being sued for everything he had left, bankruptcy followed, as well as hard time behind bars!

Times have changed, however. In August 2020, Dykstra announced he had gone 27 consecutive months without being arrested! While that’s a good start, he surely regrets the crimes and shady dealings that landed him with those jail sentences.

BRASH BRUNELL

Call it sad, but some folks are fans of the Jacksonville Jaguars. And, if you’re a Jaguars fan, you’ll know the meaning of the word “lose”. Things were no different back in the late 90s, and the long-suffering team were ready for a star player to join their ranks – enter Mark Brunell!

While Brunell couldn’t get them to the Super Bowl, the quarterback still went down as one of the best players in Jaguars history! And, with a career like that, you can bet the coin came a-callin’!

Over the course of his career, Brunell made nearly $70 million. That would surely be enough to keep him comfortable for the rest of his life! No need for Brunell to make risky investments in something like fledgling fast-food companies, right!?

Well, tell that to the $9 million Brunell sunk into the fast-food chain Whataburger. Brunell spent a fortune setting up Whataburger restaurants in and around the Jacksonville area. But the people of Jacksonville weren’t as keen on Whataburgers as Brunell thought, and the restaurants began to hemorrhage money.

At the same time, the quarterback was sinking $11 million into a company ironically named Champion LLC. But that money – used to invest in the real estate market – was lost to the great housing market crash of 2008, and Mark was left with no other option than to file for a Chapter 11 Bankruptcy! And this was while he was still an active NFL player!

By 2010, he was left with only $5.5 million in assets set against almost $25 million in debts. Today, Brunell is worth only $400,000 – a lot of money to the rest of us but, when you’ve tasted that sweet millionaire lifestyle, there’s no going back!

SPENDTHRIFT SAPP

A defensive tackle for the Tampa Bay Buccaneers and Oakland Raiders, Warren Sapp made over $75 million during his 12-year NFL career! That was the collective pay-out of 3 lucrative pro contracts! But incredibly, it wouldn’t last the 4 time All-Pro for long.

During his playing career, Sapp had begun to develop some dangerous spending habits. He went totally overboard: splashing the cash on things like a $4.1 million mansion, a $1,200 lion skin rug and, bizarrely, 240 pairs of Air Jordans worth over $6,000!! That’s right: $6,000 on 240 pairs of the same shoe!

He also invested in needless expenses such as a large, nude painting of a woman, and a pair of boxing gloves signed by Muhammad Ali - neither of which came cheap! His spending was well and truly out of control. By 2012 the spending spree was forced to end as Sapp filed for bankruptcy.

What happened to all those gloves and shoes and lion skin rugs? They disappeared in a pool of liquidation! At the time, Sapp had only $6.45 million in assets, a little below the $6.7 million he’d accrued in debt. To pay off that debt, Sapp worked as an analyst on the NFL Network making more than $45,000 a month.

Things were turning around for him, that was until he was arrested in 2015 on solicitation charges and fired from that cushy job. Nowadays, Sapp has returned to obscurity to count his debts, discounting a brief resurfacing in court for some very illegal activity. Looks like he never thought he’d be "Sapped" of his cash!

RECKLESS RODMAN

It’s hard not to be fascinated by Dennis Rodman. Nicknamed "The Worm" for his incredible rebounding ability, Rodman earnt around $27 million during his NBA career! And at the height of his fame, Rodman was the 10th highest-paid player in the NBA!

It’s no surprise Rodman pursued a lavish lifestyle of excess! In 1996, he snapped up a two-story LA home on Seashore Drive for $825,000. The home became party-central on Newport Beach, with revelers frolicking round for what were some very expensive parties!

And, on the way down the drive, partygoing guests could ogle at Rodman’s high-priced car collection: there was the custom-painted Hummer H1, the custom-painted Lamborghini Gallardo, the custom-fitted 1996 Porsche 993TT and a retro 1959 Cadillac Convertible – and that was just a peak at his multimillion-dollar collection!

Although, he didn’t always have something to show for his expenses; he once lost a million dollars in one fell swoop back in 1997, when he kicked a referee in the groin and found himself facing a fine and an 11 game suspension. That was one expensive mistake that, it turned out, he really couldn’t afford to make.

By 2012, the Worm had finally splashed all the cash on his weirdly outrageous lifestyle. That year, Rodman appeared in court to address charges that he owed $800,000 to his ex-wife in child support. There, Rodman’s lawyers claimed the player had no means to pay the money – because the former millionaire had no money!

Barely clinging onto any of the earnings he had left, today rodman is worth less than 2% of his NBA earnings at just $500,000. For a player who could’ve been set for life, it shows just how quickly those riches can go away.

BORIS’ BILLS

There have been very few careers as triumphant as Boris Becker’s! Between 1985 and 1996, Becker won 3 Wimbledon championships, 2 Australian Opens and 1 US Open. With all that success – and a singles career win-rate of 76.9% – you can bet the money came rolling in!

From prize money alone, Becker earnt a mouth-watering $25 million! But that wasn’t even half of it. Literally. Through sponsorships and endorsement deals, Becker made another $105 million – totaling career earnings of $130 million!

But, unless you’re careful with your millions, the cash can go quickly! After retiring in 1999, a bitter divorce with his first wife, Barbara Feltus, cost the player $25 million alone! In the separation, Becker lost a luxury condo in Miami, and was forced to pay another $1.2 million buying Feltus property in London.

Becker’s debts would only increase in 2002, when the German government revealed he had evaded $3 million in taxes. To avoid prison, Becker was forced to accept a huge fine of €300,000 – a little over $450,000 today.

Ten years later, and Becker was still faulting on debts, this time on a luxury villa in Majorca. The 62-acre property – complete with basketball court, guesthouse, and orange grove – would cost the one-time rich guy money he simply no longer had!

All these near misses finally came to a head in 2017 when, having blown through nearly all of that $130 million, a British judge declared Becker bankrupt! Although the court hesitated to give a concrete number, it was reported that he was in a staggering $54 million worth of debt.

Becker would end up auctioning off his hard-earned trophies, raising $937,823 in the process! But not even that was enough to save him from a 2019 decision to extend his bankruptcy restrictions all the way to 16th October 2031. A decision made after the ever-responsible Becker was found to be hiding assets worth over $6.1 million!

GEORGE’S WORST

From 1963 to 1974, George Best - the iconic player for soccer team Manchester United - scored 137 goals in 361 appearances for the team, cementing his place as a club legend! All that success didn’t come without notoriety, however.

Best also holds the distinction of becoming one of the first celebrity soccer players. At the height of his fame, he was making the equivalent of $1 million a year – that’s a little over $7 million a year in today’s money. Much of that was used to fuel the player’s hedonistic partying, which Best didn’t deny!

When Best filed for bankruptcy in 1983, he openly admitted to spending a whopping 90% of his money on women, drink and fast cars. This also meant he couldn’t afford to pay a £16,000 unpaid tax bill. The sum ballooned to £60,000, roughly $200,000 today, in the 10-year wrangle that followed.

Inevitably, shortly after he retired in 1984, the superstar was totally broke. With his partying had come alcohol addiction, and eventually illness. His final words – published in the News of the World – read simply, “Don’t die like me.”

IMMODERATE IVERSON

Nicknamed “the Answer”, Allen Iverson is considered one of the NBA’s best ever players. To put his success in perspective, Iverson’s play-off scoring average of 29.7 points per game is second only to the legendary Michael Jordan!

Over his 15-year career, Allen Iverson raked in a dumbfounding $155 million! However, Iverson didn’t invest it. Or save it. Like many of the squandering stars in this list, Iverson straight up spent it!

His monthly expenses included $10,000 on clothes, $10,000 on restaurants and more than $10,000 on groceries. Indeed, 10,000 bucks on toilet paper and onions a month! That’s because Iverson bought for his entire entourage, which could include as many as 50 people.

Iverson trusted his friends, but that might not have been the best decision. Suspicious of banks, Iverson would keep all his cash in garbage bags lying around his mansion. And, on occasion, a bag or two would mysteriously go missing! Doesn’t take a genius to figure out where it was probably going.

But it wasn’t as if Iverson wasn’t squandering the dough himself! His friends revealed that he’d routinely drop between $30,000 and $40,000 a night in strip clubs. Anecdotally, this happened so often that Iverson would scoop up his own money from a previous night – and toss it down a second time!

His wastefulness continued and continued. At one point his spending was so excessive that – upon departing a flight at the airport – Iverson bought a whole new car when he forgot where his ride was parked. Now, that’s just boasting!

Because of needless escapades like that, all of Iverson’s assets had been drained by 2012. The player was forced to declare himself bankrupt when he was unable to pay a $900,000 debt to a jeweler in Georgia. That's a serious amount of bling.

But fortunately, Iverson had one lifeline remaining! A unique sports endorsement contract with Reebok meant Iverson had a lifetime deal, including payments of $800,000 a year and a $32 million trust fund he’ll gain access to in the year 2030.

So, despite his recklessness, in a few years Iverson will probably be back to his old spending habits. The strippers must be rejoicing now!

RUINOUS RANDY

During his 12-year career in the NBA, Randy Brown earnt a $15 million fortune! They were 12 successful years for Brown, who won 3 championships with the Chicago Bulls, a team spearheaded by the return of Michael Jordan.

Of all the NBA championship rings to have earned, those are by far some of the most valuable! It’s these types of historic accolades most basketball players can only dream of one day owning!

But Brown’s time with his championship rings wasn’t to last! After poor investments in real estate and restaurant businesses, Brown was left with no choice but to declare bankruptcy in January 2008. And guess which valuable assets the player was forced to auction off? Yes, it was the rings!

In an extremely painful decision, Brown was forced to sell his 3 rings – the crown jewels of his career- to the debt collectors! An anonymous bidder paid $53,833 for all three, but that reportedly barely made a dent in the debt that needed to be repaid.

CARELESS CANSECO

With 462 home runs under his belt, Jose Canseco’s baseball career saw two World Series titles with the Oakland Athletics and New York Yankees. Canseco was one of the MLB’s best: a six-time all-star, and home run leader in both the 1988 and 1991 seasons.

And, as we know, premium success means premium cash! With Canseco banking a healthy $55 million fortune, the slugger looked set for life! If only he hadn’t mired himself in a disastrous cascade of bad decisions, divorces, and tax crimes!

In 2008, having been out of the game for about 9 years - Canseco was hit by the housing crisis and had to foreclose on his 7,300 square foot mansion in Los Angeles, on which he owed the bank more than $2.5 million.

That year, he claimed his two divorces had also cost him a hefty $7 to $8 million each! He also claimed that when the stock market crashed, he lost a further $11 million! Canseco’s lowest moment came when he wound up living in a friend’s garage with only $20 to his name!

In 2012, a reporter revealed that Canseco still owed the IRS $1.1 million in unpaid taxes. That year, he filed for Chapter 7 bankruptcy.

Sadly, it hasn’t gotten much better for him. In 2021, Jose took an offer of $50,000 to star in an amateur boxing match against a barstool sports intern. He was humiliatingly defeated in less than 10 seconds.

Scrapping for $50,000 is a long way from the $55 million he was once handed! But recently, Canseco claimed that he gets by just fine and is no longer plagued with legal issues. I mean, you have to commend a guy who gets up after he’s been knocked down like that!