10 Surprising Bankrupt Athletes

Former heavyweight boxing champ Mike Tyson is perhaps the least surprising entry in our list of rags-to-riches-to-rags athletes. An elementary-school dropout raised on the mean streets of Brownsville, Brooklyn, Tyson was savagely bullied until he began street fighting for money when he was 11 [source: Tyson].

After stints in a string of juvenile detention facilities, 13-year-old Tyson was taken under the wing of boxing trainer Cus D'Amato, who predicted the lisping, emotionally scarred brawler would become the youngest heavyweight champion in history. D'Amato was right.

At his peak, Tyson was earning $30 million for a single fight and is said to have earned more than $400 million during his roller coaster of a boxing career. A world champion at the tender age of 20, Tyson's bank account greatly outpaced his maturity. According to legal records from one of his two divorces, Tyson spent:

Uneducated, emotionally stunted and desperate for a father figure, Tyson put his trust in characters like boxing promoter Don King, whom Tyson eventually sued for stealing tens of millions of his earnings [source: CNN]. The former champ filed for Chapter 11 bankruptcy in 2003 with debts of $23 million to the IRS, divorce lawyers, and an ex-wife.

Maybe bankruptcy is contagious. If Mike Tyson is the champion of professional boxing busts, could he have infected Evander Holyfield during the infamous "Bite Fight" of 1997, during which a frustrated Tyson bit off a chunk of Holyfield's ear and spit it into the stands? Or maybe there's a more reasonable explanation for Holyfield's financial woes, like fathering 11 children with nine different women?

Holyfield was paid $34 million for the Bite Fight and earned more than $560 million during his long boxing career, which included six heavyweight titles [source: Hubbard]. But all of that child support added up fast. So, presumably, did the electric bill at his 54,000-square-foot (5,017-square-meter) Atlanta mansion with 109 rooms, 17 bathrooms, three kitchens and a bowling alley [source: AP].

Crippled by debt and unable to make mortgage payments, Holyfield was evicted from his colossal home and forced to auction all of his boxing memorabilia -- including the gloves, boots and robe from the Bite Fight -- to pay millions in legal fees and overdue child support [source: Hubbard].

At 5 feet 10 inches (1.8 meters) and 160 pounds (72 kilograms), Lenny Dykstra was never a physically imposing baseball player, but his on-field tenacity and clutch heroics for the New York Mets in the 1980s won him the nickname "Nails." Dykstra earned more than $36 million in his MLB career, but some of his biggest paydays came after retirement [source: Wilson].

The former baseball player invested heavily in the stock market and in real estate, even promoting himself as a self-taught financial guru. He was a frequent and outspoken guest on cable financial advice shows and published his own investment guide for athletes called the Players Club. For all of his Wall Street savvy, however, Dykstra failed to forecast the housing bust and stock market collapse of 2007.

Dykstra's fall from financial grace was even uglier than his late '80s mullet. After declaring bankruptcy in 2009, he was convicted of bankruptcy fraud for trying to sell or destroy property that should have belonged to his creditors. His sentence of six months was served on top of an existing conviction for grand theft auto [source: Schilken]. Dykstra also made court appearances for indecent exposure and drug possession [source: Chan]. Say it ain't so, Nails!

Bernie Kosar, the famously brainy Cleveland Browns quarterback (he graduated from the University of Miami in only two-and-a-half years), took his share of bone-crunching hits in the NFL, including blindsided sacks from Lawrence Taylor, Joe Klecko and other defensemen twice Kosar's size that knocked out four of his molars. But Kosar took some of his worst hits off the field in a string of financial meltdowns and personal crises.

A consummate entrepreneur, Kosar launched businesses while still an NFL player, including ownership of a 6-percent share in an outsourcing company that sold for $500 million [source: Le Batard]. He bought an arena football league team, launched a company that built football websites and magazines, and bought loads of real estate in Florida, which unfortunately turned out to be ground zero for the housing collapse [source: Schoenberger].

Kosar was successful enough to have a wing of the University of Miami business school named after him, but he was also generous with teammates and family that asked him for personal loans [source: Le Batard]. Maybe too generous. At various points, Kosar estimates he was spending in the "eight figures" to support 25 to 50 different families [source: Holmes].

When Kosar filed for bankruptcy in 2009, he owed $9.7 million to Florida Bank for failed real estate deals, $3 million to his ex-wife, and hundreds of thousands more to friends for personal loans [source: Shoenberger].

Dorothy Hamill is not only one of the greatest figure skaters to ever grace the ice, but her personal style and girl-next-door charm helped launch a mid-1970s haircut craze. At 19 years old, an underdog Hamill won the figure skating gold medal in Innsbruck, Austria in 1976. Her trademark wedge haircut became the go-to style for millions of American girls and earned Hamill lucrative endorsements, including commercials for Clairol "Short & Sassy" conditioner [source: Hilton].

Retiring from amateur skating, Hamill earned the first-ever $1 million contract for a female athlete when she signed with the newly launched Ice Capades [source: Hilton]. Hamill eventually bought the Ice Capades franchise with her second husband, one of several risky business decisions that ultimately led her to declare bankruptcy in 1994 [source: Celizic].

In a tell-all memoir published in 2007, Hamill detailed her lifelong battle with depression and her personal trials, including two divorces and the tragic death of her first ex-husband — "the love of my life" — in a plane crash [source: Celizic].

The hair, the headband, the epic Wimbledon battles with John McEnroe and Jimmy Connors: Swedish tennis legend Bjorn Borg had one of the greatest, yet shortest, careers in professional tennis. With his emotionless bearing — perhaps only in comparison to McEnroe's and Connors' notorious outbursts — Borg won his first Wimbledon at barely 20 years old. He would win a total of five titles on the grass at Wimbledon and six more in the French Open, all before retiring at the ripe old age of 26 [source: Collins].

Borg was smart and likeable, and new friends and business partners swarmed the handsome champion. While Borg was living in swinging Monte Carlo, his colleagues and clients would run up monumental tabs on Borg's dime and jet off to exotic locations in his private plane. When his luggage and sportswear venture went south, he was forced to declare bankruptcy in 1989. The only reason he lived in Monte Carlo was to escape the punitive tax rates of Sweden, whose government hounded Borg for $40,000 in back taxes [source: Campbell].

Three marriages and two divorces later, Borg narrowly missed declaring bankruptcy again in 1997, but has restored his wealth through a now-successful clothing and sportswear venture called simply Bjorn Borg. Impossibly, it doesn't sell headbands.

When sprinter Marion Jones was at her prime, she received $70,000 to $80,000 per race, plus $1 million a year in endorsement deals from brands like Nike, which was proud to brandish its trademarked swoosh alongside her trademarked abs [source: Pugmire]. In the 2000 Olympic Games in Sydney, Australia, the fastest woman on Earth accomplished something no female athlete had done before, winning five medals in track and field, including three golds.

Fast, beautiful and rich, Jones appeared to have it all, including a sprinter boyfriend in fellow Olympic medalist Tim Montgomery. But the speed queen's success would soon come to a screeching halt. Both Jones and Montgomery would be stripped of their Olympic medals after each confessed to using performance-enhancing drugs as part of the infamous Balco doping scandal [source: Schmidt and Zinser].

Unable to race, Jones and Montgomery struggled to maintain their lavish lifestyle, which included three luxurious homes in North Carolina [source: Pugmire]. Desperate for cash, Montgomery turned to a drug-dealing acquaintance who hooked them up with a $1.7-million check-cashing scheme [source: Lelinwalla]. The crime would land Montgomery in prison; Jones served her own short sentence for lying to a federal grand jury about her doping past.

When Jones declared bankruptcy in 2007, she claimed to have $2,000 to her name, and the banks foreclosed on her three homes [source: Pugmire].

Hall of Fame MLB pitcher Gaylord Perry is as famous for his on-the-mound antics as his remarkable 314 wins and 3,534 strikeouts in the 1970s and 1980s. During his long and storied career, Perry's name became synonymous with the "spitball," an illegal pitch doctored with spit, Vaseline or hair tonic that starts fast, then drops like a rock [source: Armour]. Perry admitted the crime in a 1974 memoir, but was never officially sanctioned — rumor has it that dozens of other pitchers were equally "greased."

While still playing, Perry bought 400 acres (161 hectares) of land in rural North Carolina as a retirement plan. Perry grew up on a farm nearby, plowing fields at age 7 to help his sharecropper parents raise tobacco, corn and peanuts [source: Armour]. After pitching for 22 years in the majors, Perry's dream was to ride his tractor into the sunset. Unfortunately, the economics of family farming were against him, and he was forced to declare bankruptcy and hand the farm over to the bank in 1986 [source: Mayo].

With a name like Swoopes — a perfect combination of "swish" and "hoops" — this women's basketball phenom was destined to be a legend. Sheryl Swoopes dominated on the court from day one, regularly scoring over 50 points in her college career, and winning four WNBA championship titles, including three MVP crowns. Dubbed the "female Michael Jordan," Swoopes became the first female athlete to have a shoe named after her: the Nike Air Swoopes [source: Conway].

WNBA money isn't NBA money, but Swoopes earned $90,000 a season and supplemented her income with stints in international leagues and with endorsements from Nike and other brands. Unfortunately, like many other young athletes who grew up poor, Swoopes admits that she didn't know how to manage her newfound wealth and surrounded herself with the wrong people. When she declared bankruptcy in 2004, she owed more than $700,000 to creditors, including $275,000 to the IRS [source: Robbins].

Swoopes' financial situation got so bad that when she was released from the Seattle Storm in 2009 — after attempting a Jordan-like comeback in her late 30s — she couldn't afford to pay the rent [source: Conway]. In 2013, Swoopes settled into a stable job as the head coach of the women's basketball team at Loyola University Chicago.

Johnny Unitas is arguably the greatest quarterback in the history of the NFL. During his 18 years as a pro, "Mr. Clutch" won three NFL titles for the Baltimore Colts, was named NFL Player of the Year three times, and attended 10 Pro Bowls [source: Pro Football Hall of Fame]. His record of consecutive games with at least one touchdown pass (47) stood for 52 years until 2012 [source: ESPN.com].

Unitas is worshipped as a minor deity in Baltimore, where fans touch the late quarterback's statue for good luck outside the Baltimore Ravens' stadium. But for all of Unitas' heroics on the field, he often ended up on the losing end of post-football business deals. Several of his ventures went belly up, including a restaurant, a bowling alley and an air shipping company [source: The Washington Times].

Unitas and his second wife filed for Chapter 11 bankruptcy in 1991 after they were unable to pay back business loans for the purchase of a company that manufactured circuit boards [source: Singletary]. Unitas was still able to capitalize on his famous name with a merchandising and licensing company called Unitas Management. But after the football legend's untimely death from a heart attack in 2002, members of his family fought in court for control of the company, which also went bankrupt in 2004 [source: The Washington Times].