Shortly after her arrest last year, she posted a long statement on her Tumblr page in which she said, "I did whatever needed to be done in order to insulate my family from the climate of hostility, false entitlement, manipulation, racial prejudice, sexism and ageism that I was surrounded by." But apparently she did too much that left her more exposed to the very threats she was hoping to avoid, which she describes as "a lifestyle that required distortion and compromise." Now, rather than having to compromise her values at the behest of recording industry executives, she finds herself in the weaker position of having to answer to government and law enforcement officials, far more difficult negotiators. Mind you, not paying taxes could have been a reasonable gamble. Other high-income tax evaders -- even celebrities who could serve as high-profile examples for prosecution -- aren't necessarily jailed if the court sees another solution. Robert Frank, writing a blog for CNBC, gives some examples: Mary Estelle Curran, an elderly Florida socialite who pleaded guilty to not paying tax on $40 million income hidden in offshore accounts. She was first sentenced to probation, then had her probation revoked, allowing her to go free.
Singer Willie Nelson owed the IRS $16.7 million in 1990 according to Time Magazine; some of his property was seized. Actor Nicolas Cage had a lien filed against his real estate holdings by the IRS in 2010 as a result of owing $14 million. Criminal charges were never filed in either case. Actor Wesley Snipes, on the other hand, did go to jail, but only after he defended his decision to not file a tax return by claiming he was a nonresident alien, apparently on bad advice from his accountant. The IRS, and the judge, disagreed. He served three years in a white-collar prison.