18. Stephen Baldwin
We figured that at least one of the several Baldwins was going to help Stephen out, but nothing happened. In 2009 he owed $2.3 million and nearly escaped jail time.
Definitely the least popular and successful of the Baldwin bros, Stephen still managed to maintain a pretty much constant presence, if not so much in the movies then definitely on television. But in 2009, he filed for Chapter 11, meaning he sought protection from bankruptcy (but basically declared himself bankrupt) because he managed to amass over $2.3 million in debt to various creditors. He owed some $1.2 million on mortgages for his two New York City homes and another $1 million in back taxes, as well as a credit card debt. How he managed to become so indebted was not explained during the hearing.
His troubles didn’t end there. In 2012 Baldwin was charged with owing the state of New York $350,000 in unpaid taxes.