Toni Braxton, recording artist
Braxton has sold more than 40 million albums in her career so far. But she’s filed for bankruptcy twice – in 1998, due to an abominably one-sided new artist contract with LaFace Records; and in 2010, after abruptly canceling a one-woman Las Vegas show because of her unexpected battle with lupus, leaving her with up to $50 million in debt.
Braxton has since launched a comeback with a hit reality TV series, The Braxton Family Values, a Lifetime movie, a Broadway stint, and a new collaboration album.
Braxton recently made the news when she purchased a $3 million home in the exclusive gated community in Calabasas, California, just six months after settling her second bankruptcy.
Terrell Owens, NFL legend
Owens earned an estimated $70 million throughout his football career as a wide receiver. By 2012, he had blown through most of his fortune. Financial setbacks forced Owens to sell several of his high-priced homes for under market value; he was inundated with child-support payments upwards of $50,000 a month to four different women; and he was recently hit with a tax lien of nearly $500,000.
Owens has succeeded in reducing his child support payments. According to TMZ, last April he sued his financial advisers for “opening a bank account without his knowledge and then forging his signature, and leading him to really bad investments, including a failed Alabama casino.”
The talented football player has tried his luck at a comeback, but no NFL team has been willing to take a gamble on him.