13. Dean McDermott
Deans troubles with money and the law are nothing short of legendary. After being slapped with eight counts of contempt and possible jail time over Mary Jo Eustaces claim he owed more than $100,000 in child support, things looked dim. And that was just the beginning. Traveling further south down bankruptcy avenue City National Bank and American Express lined up to call in almost $500,000 from the defunct couple. However, Dean is not one to panic. He went out and bought a new Victory motorcycle for $15,000. This was in addition to another bike he owns worth almost $30,000.