Toni Braxton
Twice in her life, Braxton was required to file for bankruptcy. In 1998, she was forced to file for bankruptcy due to her recording contract which was paying her almost nothing. This wasn't reinforced by her wild spending habits. She had to file again more in 2008 when she was forced to cancel a tour due to recurring health problems. These days, however, Toni Braxton is doing the best she's ever been!
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