Terrell Owens, American football wide receiver who played 15 seasons in the National Football League was once worth $70 million dollars and now has an estimated net worth of $0 dollars. A six-time Pro Bowl selection, Owens holds several National Football League records and features in the all-time top five in several receiving categories including yards and touchdowns. Owens claims his financial problems started when his financial advisors put him in a series of  risky, highly leverage ventures that he didn’t discover until 2010. He also bought lots of luxury real estate, houses and condos, which he figured he could rent out if need be. When the market collapsed in 2008 Owens was left with dead weight and a series of mortgages that totaled $750,000 a year. His biggest failure was his $2 million dollar investment in an ill-fated Alabama entertainment complex with an electronic-bingo component. The venture turned out to be illegal in Alabama and violated the NFL’s policy prohibiting players from investing in gambling. Owens is suing those responsible for asking for his investment. On top of bad investments, Owens pays four different women thousands in monthly child support.

Jose Canseco, Cuban-American former Major League Baseball (MLB) outfielder and designated hitter has been around the bases, financially speaking. In the mid 1980′s Canseco won the Baseball America Minor Leasgue Player of the Year Award and was a late season call-up for the Oakland Athletics. In 1986 he was named the American League’s Rookie of the Year, with 33 home runs and 117 runs batted in. The following year Mark McGwire joined the Oakland Athletics and together, he and Canseco, known as the “Bash Brothers” formed a fearsome offensive duo. in 1990 Canseco signed a $23.5 million dollar contract over five years to become the highest-paid baseball player in history. Canseco’s 17-year career was impressive but ultimately tainted due to his rampant use of testosterone injections. Over his career, Canseco made $300 million dollars and spent almost all of it. Last year he owed $500,000 in back taxes. He blames his financial loss on bad investments, shady business deals, and untrustworthy friends. Some blame it on ego. Canseco regularly tweets about his money problems, business prospects, and baseball fantasies on his Twitter, follow him here.

M.C. Hammer, American rapper, entertainer, and dancer has a current estimated net worth of $1.5 million dollars. In 1991 Hammer was at the peak of his career, earning more than $33 million dollars. His album earned Diamond Status, the first time a rap album has won the award. He spent his considerable fortune on dozens of luxury automobiles, planes, a record company and a 12-acre home in Fremont, California. Hammer spent $30 million dollars building the home from the ground up in the hills above the rough neighborhood we he grew up…perhaps not the wisest investment. The 40,000 square foot mansion included a bowling alley, two swimming pools, multiple tennis courts, baseball diamond, recording studio, Italian marble floors, and a 17 car garage. Hammer was also famous for having a large entourage, reportedly spending $500,000 a month on his entourage’s bills. Hammer filed for bankruptcy in 1996. He was $14 million dollars in debt. His mansion went into foreclosure and was sold for $6.8 million, $23,200,000 dollars less than the building price.