Top 10 Tax Dodgers

“Most of us” being the operative term – a few delinquents try to fool the tax collector, but it usually only works for so long. Here are 10 of the biggest (and most famous) tax dodgers.

Willie Nelson

It’s tough to be mad at Willie Nelson. So when Willie got into tax trouble, his fans were there to bail him out. After the IRS hit the country crooner in 1990 with a bill for $16.7 million in unpaid back taxes, Nelson had to hand over many of his possessions to stay out of prison. But in a bit of quick thinking, he released an album poking fun at his plight, calling it The IRS Tapes: Who Will Buy My Memories? His fans took the title literally, snapping up his items at auction but then handing them back over to Willie. By 1993, Nelson was able to settle his tab.

Richard Hatch

Richard Hatch outwitted, outplayed and outlasted everyone on the first season of Survivor. The Internal Revenue Service, however, is a completely different kind of opponent. Despite being one of the most publicized TV-show winners ever, Hatch somehow thought he could get away with not paying taxes on his million-dollar bounty. A Rhode Island jury sentenced him to 51 months in prison for his forgetfulness. No word on whether Hatch has managed to scheme his way to being king of the jailhouse just yet, but he doesn’t have much longer to go. His release is scheduled for October.

Leona Helmsley

Leona Helmsley will always be remembered for one of the most arrogant statements ever uttered: “We don’t pay taxes. Only the little people pay taxes.” A touching sentiment from the New York hotel tycoon widely dubbed the “Queen of Mean” but not one shared by a jury of her peers. In 1989 Helmsley received 16 years in prison for a wide variety of tax offenses resulting in several million dollars owed. And in a fitting bit of chronology, the judge ordered her prison sentence to start on April 15 – Tax Day!

O. J. Simpson

For a man who never met a legal problem he didn’t like, O. J. Simpson finds his tax troubles the least of his concerns. The CourtTV regular was one of a slew of celebrities called out by California when the state released a list of its most delinquent citizens. The Juice apparently owes the state $1.4 million in back taxes. Good luck collecting that, though. Tracking down the ex-football star isn’t the issue. He’s living in a Nevada prison on a kidnapping and armed-robbery conviction for the foreseeable future.

Dionne Warwick

Dionne Warwick’s father was an accountant. Paying taxes should be in her blood. Earning dozens of hits throughout her decade-long career as a vocalist apparently wasn’t enough to keep Warwick of California’s list of the most delinquent tax payers, with outstanding bills of more than $2 million. Unlike many other tax scofflaws, Warwick, who now lives in Brazil, is at least making an effort to pay down her remaining debt. Her publicist says she is working with California to correct her expensive…oversight.

Sinbad

Joining O. J. Simpson on the list of California’s biggest tax debtors is comedian Sinbad, who owes the Golden State $2.5 million in personal income tax. The most surprising part about this is not that Sinbad owes taxes – it’s that he owes so much. A bill for $2.5 million seems a little steep for a man whose last widely seen role was in Jingle All the Way.

Walter Anderson

Walter Anderson doesn’t have the same cachet as other names on this list, but he makes up for it with the sheer scope of his crime. A telecommunications entrepreneur, Anderson strung together an elaborate network of offshore companies and aliases to hide money. The result? More than $200 million in taxes owed to the Federal Government and the District of Columbia. To date, it’s the largest tax-evasion scheme ever, and in 2005, it all came crashing down. Anderson pleaded guilty and was ordered to pay nearly $400 million after penalties and fees.

Lauryn Hill

Legendary hip hop artist and eight-time Grammy winner Lauryn Hill could face up to the three years in prison after pleading guilty to tax evasion charges. The South Orange, N. J. native and mother of six admitted in a state court that she hadn’t filed tax returns from 2005 to 2007. During that time, Hill, now 37, had earned more than $1.5 million. When news of her tax troubles began to spread across the Internet a few weeks prior to her trial, Hill took to her Tumblr account to explain the ordeal. She wrote that she had done what was necessary to insulate her family from the “hostility, false entitlement, manipulation, racial prejudice, sexism and ageism” surrounding her. Hill will return to court for sentencing in November.

Al Capone

At his peak, Al Capone was America’s most powerful mobster, overseeing a massive Chicago crime syndicate during Prohibition’s heyday. So what would finally take down this kingpin? The betrayal of a loyal associate maybe? A brutal mob murder? Please. This isn’t the movies. The Godfather’s tendency to not pay his taxes would prove his downfall. Unable to nail Capone on racketeering charges, authorities found him guilty of tax evasion and sentenced him to an 11-year prison term. By the time he was released, Prohibition was kaput, and other mobsters had taken over his organization.

Wesley Snipes

Wesley Snipes tried nearly every defense to avoid paying taxes. Star of the Blade trilogy and White Men Can’t Jump, Snipes narrowly escaped tax-fraud charges in 2008 after a lengthy trial in which he blamed his advisers for bad information and claimed, at various points, that the IRS was an illegitimate government agency, that he was a nonresident alien, that he had received bad information from his associates… and on and on. The excuses weren’t enough to dodge a conviction on the charge of not filing a tax return, and Snipes received a three-year prison sentence for his malfeasance.

Pete Rose

The IRS couldn’t have cared less whether Pete Rose bet on baseball or not – it just wanted him to pay his damn bills. The disgraced ex-slugger failed to properly report income from autograph and memorabilia sales and gambling wins (horses this time). And even after Rose pleaded guilty to federal tax-evasion charges in 1990 and spent five months in prison, his troubles didn’t stop there. In 2004 he was hit with a nearly $1 million lien for unpaid back taxes. Rose may have batted.303 in the majors, but when it comes to accounting, he strikes out every time.


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