Leona Helmsley
Money owed: $7.1 million
Prison sentence: 4 years
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Years before the proclaimed Queen of Mean bequeathed her Maltese, Trouble, $12 million for his care after her death, the hotel magnate made headlines over a big fight with the IRS. In 1986, the Federal Government charged the billionaire with tax evasion after bitter contractors, alleging they hadn’t been paid by Helmsley, turned her in to the IRS for work they’d done at her home but charged to her business. Hemsley’s housekeeper testified that her employer had boasted; "We don't pay taxes. Only the little people pay taxes.” She was convicted, fined $7.1 million and sentenced to four years in federal prison, although she served only 18 months.
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