Toni Braxton
Toni Braxton famously filed for bankruptcy in 1998, citing her exorbitant spending habits and bad management as the cause. Toni filed for bankruptcy again in 2010, citing her expensive health problems as the cause. Last year, a court allowed US Bank to file a foreclosure suit against Braxton for money she still owed on the full price of her $1.5 million home in Duluth, Ga.