Maureen O’Connor – $85 Million
Politician Maureen O’Connor was running for San Diego City Council when she happened to meet Robert O. Peterson, the founder of the Jack in the Box fast food chain. The couple went on to marry in 1977.
O’Connor did well in her career, but two years after she resigned as mayor of San Diego in 1992, her husband died. Peterson left his wife $50 million, the equivalent of $85 million today. Struggling with the loss of her husband, the former politician developed a gambling habit. The widow was charged with money laundering in 2013. She escaped jail, but the judgement left her destitute.