Tony Romo is one of those quarterbacks that is hard to put into a box. Romo had a solid NFL career and was viable starting quarterback, but he was never able to lead his team over the hump and into the promised land of securing some championship jewelry. From 2000-2002, Tony Romo attended Eastern Illinois University where he earned Ohio Valley Conference Player of the Year Award all three seasons he played football for the program. Romo also was the first and only player in the conference to ever win the Walter Payton Award as well.
Despite his award-winning showing in college, Romo went undrafted in the 2003 NFL Draft. Fortunately, Romo was signed as a rookie free agent by the Dallas Cowboys where he would play his entire fourteen-season career. Romo didn't earn starting quarterback honors until the 2006 season where he started ten out of the sixteen regular-season games. This is when the flood gates opened exposing Romo to some blockbuster contracts and endorsement deals. In 2007, Tony Romo signed a contract worth $67.5 million and in 2013, Romo signed a six-year extension worth $108 million. Unfortunately, that contract was terminated after Romo lost his starting QB job to Dak Prescott and retired the following year in 2016. However, he still left the game with $127.4 million big ones in his pocket.
Not all celebrities have fame and fortune, some are just famous – and in a ton of debt. They came from rags to riches, then went back to rags. Whether they’ve filed bankruptcy, ended up in court, or just can’t stop spending, celebrities mismanage their money just like everyone else. They just hide it well.
50 Cent coined the term “wanksta,” then “partied like it was his birthday” until he filed Chapter 11 bankruptcy in 2015. The rapper was said to be anywhere between $10 million and $50 million in debt. In 2016, a federal bankruptcy court judge in Connecticut approved a plan for the founder of G-Unit to pay his debts back. He was able to get his bankruptcy discharged in February of the following year.
Following a 45-year-long career in Hollywood, acting in more than 70 films, actor Gary Busey found himself in more debt than he was worth. In 2012, it was reported that Busey owed between $500,000 and $1 million worth of debt, but only had $50,000 to his name. The 74-year-old actor owed money to hospitals, banks, the L.A. Waterworks District, and even a storage company. He filed Chapter 7 bankruptcy that same year. Despite his longstanding career in Hollywood, Busey's net worth is now only $500,000.
Burt Reynolds is still worth five million dollars, but his battles with debt date back more than 20 years. Between bad investments and a pricey divorce from actress Loni Anderson, the 1970s superstar had to deal with over $10 million in debt and decided to file Chapter 11 bankruptcy in 1996. While testifying in a 1994 custody hearing, the South Florida native said he spent $40 million getting through his divorce.
The former Hollywood bad boy, Charlie Sheen owes the IRS nearly $5 million. But that's not all. In 2016, his net worth was reportedly still as high as $150 million, but he was nonetheless $12 million in debt at the time – including mortgages, legal fees, and taxes. That same year, Debt.com reported Sheen owed nearly $300,000 on an American Express card alone.