5 Rich People Who've Gone Broke... More Than Once!

Celebrities making millions only to become bankrupt. while shocking, is nothing new. A lavish lifestyle, after all, can be very costly.  By owning multiple homes, expensive toys, making risky investme

Celebrities making millions only to become bankrupt. while shocking, is nothing new. A lavish lifestyle, after all, can be very costly.  By owning multiple homes, expensive toys, making risky investments and by entrusting their fortunes to the wrong hands, many people - not just celebs - find themselves filing for bankruptcy protection and often for bankruptcy itself. In the last century, the increase in divorce rates has thrown yet another wrench into the works; costly court battles, the divvying up of assets and a missing prenuptial agreement can wipe a wealthy person's bank accounts clear of funds.

It’s not just individuals who file for bankruptcy though - many business find themselves suffering hard times and are forced to declare corporate bankruptcy when they run up more debts than they have assets. It’s a complicated predicament and there are multiple types of bankruptcies that an organization, a business or a person can file for. For some, this move can be more serious than for others. Prior to moving to Hollywood and starting a movie empire, Walt Disney was forced to declare bankruptcy when his first animation company lost its financial backing. Even Henry Ford’s first two attempts at automobile manufacturing flopped, forcing him to file and start all over again from scratch.

Year after year we hear about celebrities filing for bankruptcy after years of living beyond their means – boxer Mike Tyson, once paid millions of dollars per fight, managed to spend over $400 million dollars in 20 years and found himself in debt by 2004. 1990s superstar MC Hammer once owned a $30 million mansion but within six years he was millions of dollars in debt.  While so many of those public figures have declared themselves bankrupt, several have actually been forced to file more than once. These are 5 celebrities and moguls who have resorted to filing for bankruptcy on more than one occasion.

3 T-Boz: Declared bankruptcy twice

Tionne “T-Boz” Watkins of girl group TLC first filed back in 1995 on the heels of a short-changing record deal that was highly publicized. In spite of her efforts to bounce back, T-Boz was faced with some hefty bills in the years to come including medical bills stemming from a brain tumor and her diagnosis with sickle cell anemia, plus an ex who failed to pay her child support. Unable to work much and receiving little in royalties from TLC’s many hits, she was reportedly forced to file for chapter 13 again in 2011.

4. Burt Reynolds: Declared bankruptcy twice

Actor Burt Reynolds used to get paid big bucks for his roles but his divorce from actress Loni Anderson, accompanied by some restaurant investments that didn't pan out, resulted in Reynolds being forced to file for chapter 11 back in 1996. In 2010, the Merrill Lynch Credit Corporation filed a foreclosure against him as he owed $1.2 million on his Florida home. The home was on the market for several years, but with no buyers.

3. Toni Braxton: Declared bankruptcy twice

Singer Toni Braxton first filed for bankruptcy in 1998 citing spending habits, particularly on home décor, as the chief cause. Braxton came back with the huge hit single He Wasn't Man Enough in 2000 and it looked like she was slowly but surely getting back on track. However, in 2010 she once again filed for chapter 7 as she claimed a reported $50 million in debts (although there is speculation that she owed somewhere between $10-50 million). She managed to bounce back again, though, and just last month purchased a 3 million dollar home in Calabasas, California near homes belonging to Justin Bieber and Kourtney Kardashian. We'll see how she fares this time around...

2 Billy Joel: Declared bankruptcy three times

Musician Billy Joel has had a rough go of things: A divorce from former supermodel Christie Brinkley, a battle with alcoholism, involvement in numerous car accidents and, in 2009, his only daughter's attempted suicide by overdose. To top things off, Billy has been forced to declare bankruptcy not once, but three times. He made the unfortunate mistake of trusting his brother-in-law to manage his money, which resulted in a loss of his fortune. Frank Weber was responsible for handing out loans, investing in shady ventures, double billing, forging expenses and issuing false statements to Joel, all without Joel's knowledge. Joel went on to sue Weber for $30 million worth of compensatory damages, $60 million worth of punitive damages, as well as between $15-20 million for false commissions that Weber received before being fired. In the end, the case was settled in 1993 when Joel was awarded $3 million.

1 Donald Trump: Declared bankruptcy four times

Donald Trump may appear to have all the money in the world, but believe it or not, he has actually filed for bankruptcy an incredible four times! Although his businesses have taken several hits, he's been cushioned from the blows; he's never filed for personal bankruptcy, only corporate bankruptcy. These incidences were largely related to his stake the casino industry. After filing first in 1991 and then again in 1992, 2004 and 2009, we can't help but wonder where this billionaire keeps going wrong? It’s worth noting though that when he first filed in 1991, he was in the processing of financing the Trump Taj Mahal with his own funds and had to sell off some heavy assets to repay his $900 million in debt.

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5 Rich People Who've Gone Broke... More Than Once!