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The Miscalculation of Lauryn Hill

NEW YORK ( TheStreet) -- The upshot of former Fugees star Lauryn Hill's legal troubles is that we may see a new studio album from her, the first in 15 years, on her own label, through a deal arranged with Sony (SNE - Get Report). The downside? Prison, and three months without being able to pursue her career or be with her kids.

It seems Ms. Lauryn miscalculated.

Here's a brief rundown of the available facts, simple and strange as they may be. More interesting is what's underneath, sweeping themes that together weave a tale of operatic proportions.

Hill was sentenced Monday to serve three months in jail for not paying taxes on an estimated $1.8 million in income from 2005 to 2007. It took her a long time to get around to it, taxing the court's patience, but by the time she was sentenced she had paid $970,000 in federal and state taxes, apparently the total owed excluding interest and fines.

The judge could have sentenced her to three years. Her attorney asked for probation. The judge gave her 90 days plus another nine months of supervised release. She is to start her sentence July 8.

According to media reports, Hill testified in court that she always intended to pay the back taxes but found herself unable to do so when she left the music industry in an effort to protect and care for her six children.

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.
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