At first blush Leona Helmsley and Ann Romney would appear to have nothing in common. Helmsley, after all, looked the part of her moniker "the Queen of Mean" given to the imperious, stern, dark haired billionaire real estate mogul for her legendary mis-treatment of the poorly paid folk who cleaned up after her. On the other hand, the sweet, blond, soft spoken Romney, appears to be the perfect wife, mother, sister, aunt, grandmother one could possibly imagine.
Alas, the two have more in common than meets the eye. Helmsley, who died in 2007, and Romney, running hard to become First Lady, both amassed immense wealth and worked very hard to pay as little tax as possible. Hemlsley and her husband, Harry, engaged in all sorts of illegal schemes to avoid taxes including having contractors on their private dwellings send the invoices to their hotels as business expenses. These shenanigans eventually landed Leona in the hoosegow for tax evasion and extortion. Ann Romney, and her husband, presidential contender Mitt, may not have broken a single law or mis-treated a single business associate in conformance with their image. But they sure haven't paid much tax, either, as far as we can determine from their meager financial disclosures. Ann and Mitt did it the old fashioned rich way - off shoring as much income as possible to the Cayman Islands, Bermuda and Switzerland.
Back in 1989, Leona Helmsley was quoted at her trial as telling her housekeeper: "We don't pay taxes. Only little people pay taxes". Ann Romney told an interviewer 23 years later when questioned about her finances: "We've given you people all you need to know."
To paraphrase novelist F. Scott's Fitzgerald's most famous quote: "The rich are very different from you and me.....they pay less taxes".