T-Boz of TLC
The TLC singer filed for bankruptcy in 1995 and in 2011. Then last year, a judge dismissed her third bankruptcy case because T-Boz reportedly made no effort to settle her affairs, pay off her debts or appear at a creditors’ meeting. Hopefully her recent TLC network show, Totally T-Boz, generated some cash!
The first time Tionne “T-Boz” Watkins filed for bankruptcy was in 1995, after a famously short-shifting record deal from LaFace Records. The second time was in 2011. Watkins doesn’t have a history of living a lavish lifestyle, at least according to her public profile, however she hadn’t been working much to supplement her reported $1200 a month in royalties.
In addition, Watkins had been burdened by medical bills after suffering from a brain tumor and sickle cell anemia. Her ex-boyfriend and child’s father Mack 10 has not settled on the reported $250,000 due in delinquent child-support payments.
The multi-platinum artist had a much better year in 2013 when VH1 premiered the biopic “CrazySexyCool: The TLC Story.” Watkins also joined her bandmate Chilli to release new songs.
Evander Holyfield, heavyweight boxer
Holyfield earned over $200 million dollars during a career that spanned more than two decades. The boxer had been teetering on the brink of financial ruin for sometime when his 109-room mansion in Atlanta went into foreclosure in 2008. He would hold off the foreclosure for a few years, but was forced to put the home on the auction block in 2012 to pay off $14 million he owed to financial firm JP Morgan Chase.
The home sold for $7.5 million. Holyfield owed $200,000 in back taxes and over $500,000 in child support payments as of 2012.

