Top 8 Famous Tax Evasion Cases in IRS History

The Queen of Mean

Leona Helmsley is a self-made businessperson and real estate, tycoon. She was infamously known as the “Queen of Mean,” and was popular for a quote in her tax trial, where she uttered, “We don’t pay taxes. Only little people pay taxes.” Her tax evasion story started in 1983 when her contractors sued her for non-payment of the Dunnellen Hall remodeling bill.

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Leona Helmsley during Leona Helmsley Leaving the New York Federal Court House – July 20, 1989 at New York Federal Court House in New York City, New York, United States. (Photo by Ron Galella, Ltd./WireImage)

During the court proceedings of her lawsuit, it was revealed that most of the contractors’ work was illegally billed to Helmsley’s hotels as business expenses, and because of this, a federal criminal investigation was started. Leona Helmsley was then convicted of one count of conspiracy to defraud the United States, three counts of tax evasions, sixteen counts of assisting in the filing of false partnership and corporate tax returns, ten counts of mail fraud and three counts of filing false personal tax returns. She served 18 months in federal prison, two months on house arrest and one month in a halfway house. Helmsley died on 2007 and left her Maltese dog of $12 million trust fund, which was hailed, 3rd in Fortune magazine’s “101 Dumbest Moments in Business” of 2007.

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