From reckless spending to bad investments to massive amounts of child support money, athletes can find many ways to blow their gargantuan salaries. Unfortunately for the 10 men on this list, they have been guilty of at least one of those things and more, and they’ve paid the price for it, so to speak. With that in mind, we’ll be counting down 10 of the most famous and popular athletes who went broke.

Most of them are retired from their respective sports, which has potentially accounted for their losses, if nothing else. There’s former baseball star Curt Schilling, who blew pretty much all of his $50 million earnings on his investment in a video game company that ended up failing to take off. Then there’s Allen Iverson, who blew tons of money on many lavish things that only a supremely rich person can buy. And then there’s Mike Tyson, whose lacklustre decisions with money aren’t just well documented – they’re legendary. As sports fans may be led on into thinking that famous professional athletes are drowning in millions of dollars every year, it’s still surprising that some of these athletes can blow their massive earnings for such a wide variety of reasons.

There are some definite omissions on this list – former WNBA star Sheryl Swoopes, former NBA player Latrell Sprewell and former tennis star Bjorn Borg among them – showing that going broke as a professional athlete can be a fairly common occurrence. That said, it has brought these athletes repercussions that run the risk of causing their sporting accomplishments to take a backseat entirely, and they’re then put to the task of trying to rebuild not only their finances, but their reputation. Here are 10 of the greatest athletes to have ever gone broke, whether they formally filed for bankruptcy or not.

10. George Best

He will always have a reputation as being one of the greatest footballers of his day – and also one of the greatest footballers to never play in a World Cup – but Manchester United/Northern Ireland legend George Best was not as good with money as he was with a ball. The late footballer battled alcoholism to such a degree that he needed a liver transplant, not to mention he admitted that he “squandered” a ton of money on cars and women as well as alcohol despite earning a reported $100 million in his life. The apple hasn’t fallen far from the tree either, as the hard-partying ways of his son Calum have led him to file for bankruptcy as well.

9. Terrell Owens

Known for being just as enigmatic as he was talented during his football career, Terrell Owens has also been known for going broke. During an interview he had with GQ in 2012, he admitted that he lost millions of dollars thanks to having to pay tons of money in child support  – he has four kids with as many different women – and investing his money poorly, and he also placed blame on his financial advisers. Despite his status as a potential Hall of Famer and with at least $80 million earned in his career, Owens has certainly seen as many financial trials and tribulations as NFL achievements.

8. Warren Sapp

He was known for being one of the best defensive tackles in the NFL during his playing days – and even made it as a guest star on The Simpsons – but Warren Sapp is not known for keeping a hold on his millions of dollars. The former Super Bowl winner with the Tampa Bay Buccaneers reportedly owes $6.7 million to creditors, the Internal Revenue Service, and to child support – as well as tons more in unpaid property taxes and alimony. The Hall of Famer also saw his 10,000-square-foot home be sold in an auction in 2012.

7. Scottie Pippen

He may be nicknamed “No Tippin’ Pippen”, but his lack of generosity to wait staff at restaurants hasn’t stopped this Chicago Bulls legend from losing tons of money anyway. Despite earning $120 million in his playing career, Scottie Pippen lost much of it (largely after he retired from basketball) thanks to mismanagement of his funds, causing him to sue his former law firm over it. Thanks to poor choices of investments as well as buying a $4 million malfunctioning jet that needed an extra $1 million in repair costs, Pippen has seen his pocketbook shrink considerably despite otherwise being frugal with money – at least when he goes out.

6. Marion Jones

She may have been one of the United States’ star athletes at the 2000 Summer Olympics in Sydney, but Marion Jones’ bankruptcy has proved that she is now far removed from her five-medal performance at the games – at least financially. Before seeing her $2.5 million mansion near Chapel Hill, North Carolina be foreclosed, Jones lost her endorsements and saw her medals get rescinded thanks to her admission of taking steroids before her races. On top of that, Jones also owed hundreds of thousands worth in legal fees – among other unpaid expenses – and the former track star/former WNBA player ended up going broke.

5. Curt Schilling

He’s been retired since 2008 and reportedly made $114 million throughout his career in baseball, but Curt Schilling’s inability to hang on to his money has risked transcending his accomplishments as a player. The former Red Sox pitcher saw his video game company (38 Studios) go bankrupt in 2011, losing him $50 million in the process. Even more sadly for Schilling – who recently overcame a battle with cancer and is currently in remission as of June – he tried auctioning off his bloody sock from the 2004 World Series and got a disappointing $92,613 from it. Some were expecting the top bid to be close to $400,000.

4. Evander Holyfield

Career earnings of $250 million should keep your pocketbook set for years to come, right? Well, apparently not for former boxing great Evander Holyfield. Although he’s just as well known for having had part of his ear bitten off by Mike Tyson as he is for his boxing accomplishments, Holyfield is known also for his poor handling of his money; from difficulties paying child support  for his 11(!) children (which resulted in a lawsuit against him), to his foreclosed $10 million and 109-room mansion, to the fact that he still owed $14 million despite his home selling for $7.5 million in an auction.

3. Allen Iverson

Despite being one of a number of major athletes to have built up a reputation for not tipping very well, Allen Iverson still figured out how to blow a lot of his earnings. Thanks to his excessive spending on mansions, jewelry, fancy cars, and clothes – not to mention millions more on gambling alone – the former Sixers superstar has a reputation for mismanaging his funds that stands out all on its own, leaving him essentially broke as a retired NBA player. The fact that he had a lifetime endorsement contract from Reebok to the tune of $50 million adds salt to his wounds.

2. Michael Vick

As if it weren’t bad enough that his football career has long been overshadowed by his involvement in a dogfighting ring, Michael Vick had to file for Chapter 11 bankruptcy after his release from prison in 2008. To make matters worse, the current New York Jet had managed to lose $8 million worth of endorsement money per year in addition to the termination of his $130 million contract with his first team, the Atlanta Falcons. Much of Vick’s loss of money is attributed to him paying mortgages and other expenses for his family and friends, as well as racking up lost money from bad investments.

1. Mike Tyson

Although we’ve documented Mike Tyson’s reckless spending in previous articles, it bears repeating how much money he’s blown in the past, to the point where it would be hard to keep him from being anywhere near the top of this list. From buying expensive exotic pets that he couldn’t keep, to buying a $2 million bathtub for his ex-wife, to a lot more money worth of cocaine, divorce settlements and expensive jewelry, Mike Tyson’s financial management leaves plenty to be desired. Especially since he earned a whopping $400 million as a boxer. If Tyson hadn’t been spending three years in jail thanks to rape charges against him, maybe he would’ve made more money to hang on to. Or maybe he would have blown all of that, too.