12 celebrities and their biggest money mistakes

Biggest money mistakes: There are few times in normal conversation in which the word “schadenfreude” can be thrown around. It means taking pleasure in the misfortune of another. For example, when the guy who cuts you off in traffic ends up with his beamer wrapped around a street lamp, and you think to yourself “ha, serves him right” that’s an example of schadenfreude. Chuckling at a high school bully who ends up unemployed, living in his mother’s basement into his forties is another example.

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One of the greatest examples of an event during which many people feel this complex emotion is when a widely disliked celebrity goes broke. Whether a bad actor or a repulsive singer, watching a famous person become miserable recalling their car being repo’d or their house taken by the bank, it sometimes feels good. While she isn’t completely broke, Jessica Simpson recently indicated that marrying Nick Lachey was among the worst financial decisions she has ever made.

In reality however, there are tons of celebrities who have made vastly worse decisions with money. Jessica Simpson is still loaded and we estimate her net worth at around $150 million. Not too shabby for someone who considers a former marriage to have been her worst professional choice. With that said, whether it be a poor marital decision, a stupid career choice, an addiction or even poor spending habits, here is our list of twelve formerly-successful celebrities and their worst financial blunders. While you might feel sorry for some of these beloved stars, there are a few that are worthy of more than a few chuckles.

12. Toni Braxton: Terrible Overall Financial Knowledge

We start our list off with one of the most successful R&B singers of the past couple of decades. Toni Braxton has found success in four decades (1980’s to present) but just can’t seem to handle a buck. She is notorious for living well above her means and has declared bankruptcy multiple times.

Back in 1996 was the first time she filed for bankruptcy. Over a decade later she was involved in an insurance problem with Lloyd’s of London, who refused to honor a policy that dealt with cancelled concerts. She filed for bankruptcy in 2010, as she was being sued by more companies than one person can handle. She did so once again in 2013, claiming to have nearly $50 million in debt. There was no single reason for her financial woes, it is just a matter of mishandling money, poor insurance savvy and not living within one’s means. In 2014 she bought a $3 million house, we’ll see how this chapter plays out.