Allen Iverson, at one point was considered the best personality in the game, and one of the more marketable players in all of basketball. He was definetly one of the best players, an athlete that personified heart, and playing through injury, just don’t ask him about practice. But, despite all of the hype, and talent, Iverson is rumoured to be broke. A staggering thought, after he earned $154 million in salary, and a few boat loads of cash on top of that through endorsements. So, where did all that money go? His entourage was legendary, in excess of 50 people at times, a hair stylist that travelled with him, and of course, ain’t no party like a West Coast party. Now, when you add all that up, you can imagine a couple of his homies, saying, ‘it’s all good AI, we had a good run, we did big’. At least one of them did. Makes you ask the question, who are the biggest busts in sport, who went from the court to the courthouse, and from the field to, well, the field.

Lenny Dykstra was a legend in his day, known for his playing days with the Mets, and the Phillies, he was a 3x All Star, a silver slugger winner, and a World Series Champion. When he retired from baseball, Dykstra decided to diversify his portfolio. When the magazine world tried to figure out they’d survive the success of the internet, and death of paper, Dykstra started a high-end jet charter company, and a magazine catered towards pro athletes (Player’s Club) in 2008. It wasn’t soon after that his financial status was thrown into question, a GQ article accused Dykstra of credit card fraud, skipping rent payments, bounced cheques, lawsuits, and all sorts of questionable behaviour. It was just in 2008 that he was worth $58 million, he filed for bankruptcy, he went on to live out of his car, and his property started to look more like the caves in the BatCave, than Wayne Manor. He’s since been charged with various crimes, grand theft, embezzlement, possession of cocaine, marijuana, HGH, and faces 80 years in prison. No wonder his nickname was Nails back in the day.

Do I really need to tell you about OJ Simpson? ‘Juice’ as he was known in his football days, is a Hall of Famer, 6x Pro Bowl Selection, 5x All-Pro selection won a ton of awards including the Heisman, and NFL MVP, and considered him the 40th best NFL player of all time. Oh yeah, the Associated Press also dubbed him the Man of the Year in 1973. Sounds like a swell guy eh? He was even popping up in movies, and was actually given passing grades. So, what happened? Well, he changed the way the public perceives car chases, courtroom trials, Ford Broncos, leather gloves, and he was accused of killing his ex-wife, Nicole Brown Simpson, and her then-boyfriend, Ron Goldman. After a lengthy, divisive trial, he was found not-guilty, but then followed that up with being found liable in civil trial, and then was found guilty in an attempted Vegas robbery. He was found guilty of that, and is now serving 33 years in prison.

Terrell Owens is still being thrown around in NFL rumours, he was at one point considered one of the best players in the league, but also one of the biggest headaches. Too much drama, too much complaining, too wide an assortment of big sunglasses. He spent 15 seasons in the league, earned $80 million in NFL deals alone, and is a future Hall of Famer. What’s he thinking about these days? Where did it all go wrong? Four children with four different women, child support of more than $40,000 a month, and stating that he trusted too many, too much, and now has next to nothing. For a guy who lived so much in the limelight, and seemingly had it all, he’s seemed to have bottomed out.

You know, if you came from a poor background, and were offered a crazy long term NBA contract, you’d probably ask where to sign as well. But, what if you played alongside, the greatest player of all time, and got along with him really well, what if you knew you’d likely win countless championships, and become to known as one of the best wingmen of all time. Well, if you knew all that, you wouldn’t be on this list, like Scottie Pippen. It didn’t help that Pippen made bad decision after bad decision, starting with sinking $4+ million into a Gulfstream Jet. He may not be dead broke, but, he’s nowhere he could be.

The last athlete in this list has one of the best lines ever uttered by an athlete attributed to him.”I spent a lot of money on booze, [women], and fast cars. The rest I just squandered.”George Best is often considered one of the greatest footballers of all time, a sparkling 21 year career underlining that statement. When the spotlight faded, he began to drink heavily, so heavily, that he needed a liver replacement, and served two stints in prison for drunk driving. He lived a life of such excess, that it’d make Lil Wayne and Kanye blush. It was a story of two parallels, a man who played the beautiful game, so beautifully, struggled at life. He was long accused of abusing women, something he never denied, and was caught up in a ‘Carlito’s Way’ style saga, when his good friend, and lawyer, George Carman, set out to destroy him.

Check out this excerpt:

Frank Evans, a former business partner of Best, claimed in his 2009 book, The Last British Bullfighter, that Carman offered a Manchester gangster “pots of cash” in 1973 to break Best’s legs when he discovered that Best had been having an affair with his second wife, Celia. Carman’s offer was rejected with the following warning by the gangster: “I don’t sort out domestic disputes and I’m not going to harm George [Best]. So you can take your money and go somewhere else. But I’ll tell you this – if any harm comes to George I’ll know who did it and I’ll come after you.”

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