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#8 Leona Helmsley – $2 billion
Dubbed the Queen of Mean, Leona Helmsley (born Lena Mindy Rosenthal in 1920) lived a long “rich” life that was quite different to the other criminals on this list. Married four times (twice to one husband), she was left a fortune valued over $5 billion by husband Helmsley, a multi-millionaire real estate entrepreneur at the time of their marriage in 1970. Leona, by then already a millionaire in her own right, helped grow his business, but she also encouraged him to deal in a mean, underhand way. She paid for this, first when her real estate license was suspended, and then when she went to jail for tax evasion, serving only 19 months of the 16 year sentence. When Helmsley died of heart in 2007 aged 87, she left $12 million in a trust fund for her Maltese poodle called Trouble. The amount was reduced to $2 million after objections; and the decision to do this was ranked third in Fortune magazine’s 101 Dumbest Moments in Business of 2007. The dog died in 2010 aged 12, and the money leftover went to charity.
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