No offense to Jay Cutler or his family and friends, but he earned a lot of money without ever being a reliable frontman leader for the franchises he took the field for. Don't get us wrong, he's put up some amazing numbers, but for some reason, he always came up short. Cutler attended Vanderbilt University where he started all 45 games that he played in from 2002-2005. In 2005, he was named SEC Offensive Player of the Year and helped lead the Commodores to a 28-24 victory over the Tennessee Volunteers. This was the first time Vanderbilt had beaten Tennessee since 1982, the same year Cutler was born.
Jay Cutler was drafted 11th overall in the 2006 NFL Draft by the Denver Broncos where he played his first three seasons as an NFL quarterback. While he was able to put up a career-best in total passing yards his final season in Denver notching 4,526 yards through the air, he cut ties with the team and took his talents to the Chicago Bears where he played his most prominent years. In 2009, Cutler signed a two-year, $28.9 million with the Chicago Bears and a seven-year $127.6 million extension with the team in 2014. After underperforming in the 2016 season, Cutler was cut by the Bears thus terminating his contract. Cutler retired but was called out of retirement by the Miami Dolphins after their starting quarterback Ryan Tannehill suffered a season-ending injury. Cutler signed a one-year deal worth $10 million and was asked not to return following the end of the season. However, he did end his career earning over $122 million in total.
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.