Carroll Petrie
A South Carolina native and former model, Carroll was a divorcée and mother of two when she wed her second husband, Milton Petrie, in 1978 (Carroll was wife No. 4 for Milton, who was 25 years her senior). Petrie, who built a fortune with discount department stores and a major investment in Toys 'R Us, passed away 16 years later. Carroll has since filled her days doling out her late husband's cash. She's also a prolific donor to Republican candidates and causes and backed Rudy Giuliani's ill-fated presidential bid in 2008.