12 of the Biggest Tax Cheats in History, And Why They Need IRS Tax Relief – Part 2

In Part I, we looked at six of the biggest tax debts in history, and why they need IRS tax relief. We’ll take a look at six more in Part II, picking up where we left off from last week’s post which can be read HERE. 

  1. Edward and Elaine Brown, Dental and Pest Business Owners

The couple made the news in 2007 after a standoff lasting for months at their New Hampshire home. They had been sentenced to a 63-month prison term for failure to pay taxes on $2 million. Authorities eventually captured them, confiscating explosives, booby traps, ammunition and weapons. They are now serving 37- and 35-year sentences for their lack of compliance with regard to IRS tax relief.

  1. Annie Leibovitz

Famous American photographer Annie Leibovitz owed the IRS $1.4 million in addition to penalties and interest for failure to report earnings between 2004 and 2007. A lof of these cases are usually paid up in full, settled on, or jail time is served. In either case, there is usually some sort of IRS tax relief option.


  1. Leona Helmsley, Hotel Operator and Real Estate Investor

Leona Helmsley, real estate tycoon, was tried for tax evasion in 1989 after she hired contractors to work on her 21-room mansion but billed the expenses to her business. She served an 18-month federal prison sentence. She failed to qualify for any IRS tax relief option. Upon her death, she left a $12 million trust fund to her dog.

  1. Heidi Fleiss, Hollywood Madam

Fleiss rose to notoriety after her high-profile clientele were uncovered in her multi-million dollar prostitution ring in the 1990s. She was eventually sentenced to 37 months in prison after she was found guilty of income tax evasion. She paid an undisclosed amount in taxes. She also surrendered more than $550,000 from the sale of her home and also failed to qualify for any IRS tax relief program. Can’t avoid it, death and taxes, every time.

<> SiriusXM Studio on November 16, 2011 in New York City.
<> SiriusXM Studio on November 16, 2011 in New York City.
  1. Reuben Sturman, Pornographer and Businessman

As the world’s biggest distributor of pornography at one point, Sturman failed to disclose $2.7 million of income between 1978 and 1982. His questionable business dealings included ties with Gambino mob family and resulted in many raids by the police. He was later convicted of evading taxes and served a prison sentence of 10 years. 10 years for not paying taxes? Looks like IRS tax relief was not in the cards for Reuben Sturman.

  1. OJ Simpson, Former Football Player and Actor

In 2007, the state of California declared that Simpson owed more than $1.4 million in back taxes. Simpson still receives $19,000 monthly from the NFL, which means that he needs to pay taxes on that income as well – difficult to do, since he is still in prison. In 2012, the IRS filed a IRS tax lien against his Florida home for income earned between 2007 and 2010. Interestingly enough, O.J. also failed to qualify for any IRS tax relief programs.

By working with a knowledgeable IRS tax resolution expert, you can minimize your payments, saving money in the process. For IRS tax relief, contact our office at 720-398-6088.