Bankruptcy Law Questions? Ask a Bankruptcy Lawyer.
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You're not likely going to be allowed to keep both cars....and if you pay cash for one car, you should review your bankruptcy exemptions to make sure it will be safe in Chapter 7 bankruptcy. Most states have a motor vehicle exemption that allows you to protect a certain amount of equity in your car. If you can’t fully exempt the value of your car, the trustee may try to take and sell it to pay your creditors.
But, it is sometimes easier to re-affirm a financed debt if you can prove that it wasn't a frivolous purchase, or a purchase intended to qualify you for bankruptcy.