With nine Super Bowl appearances and six rings, Tom Brady is the most decorated quarterback of all-time and arguably the greatest quarterback of all-time. The funny thing is, Brady has renegotiated multiple contracts in order to attract other big-name stars to join him in New England. And at the age of 42-years-old, Brady doesn't show any signs of slowing down. Tom Brady attended the University of Michigan from 1995 to 1999 where he didn't get his first start until his junior year. As a starter, Brady led the Wolverines to a 20-5 record and victories in the 1999 Citrus Bowl and 2000 Orange Bowl.
The greatest quarterback of all-time was drafted 199th overall in the sixth round of the 2000 NFL Draft by the New England Patriots. Brady didn't get any real playing time his rookie season but was named the starter in 2001 after an injury to then-starter, Drew Bledsoe. Since then, Brady has become the only quarterback to reach 200 wins and a 14x Pro Bowler. In 2005, Brady signed a four-year contract extension worth $48 million. In 2010, Brady signed an additional four-year extension worth $72 million. Since then, Brady has signed an additional three extensions worth over $121 million with the Patriots for his twenty years' worth of service.
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.