Leona Helmsley

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Leona Helmsley was reportedly obsessed with avoiding paying taxes.
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Leona Helmsley might have had a spare $12 million at the time of her death that she was able to leave to her dogs. There was a time, however, where she apparently couldn't cough up to pay her tax bill of a couple million dollars despite wealth in the billions.

Helmsley faced charges of tax fraud in 1992, which spawned a much-publicized trial. During the case, a witness, her housekeeper, testified that Helmsley once stated: "We don't pay taxes. Only the little people pay taxes."

Helmsley was found guilty of multiple charges and served 18 months in jail.

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