Online Poll: Who’s the Worst Tax Cheat in American History

Online Poll: Who’s the Worst Tax Cheat in American History

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America’s has had its fair share of tax cheats, but some have been worse than others.

Below is a list of five famous tax cheats and a brief description of their tax troubles.  At the end of the post is a little poll. Tell me who you think is the worst.

Al Capone

Good ol’ Al, the mastermind of America’s largest crime network, wasn’t smart enough to figure out that he had to pay taxes on his income whether or not it was legally gained.

Here’s Al’s famous quote: “The income tax law is a lot of bunk. They can’t collect legal taxes on illegal money.”

I guess his tax attorney didn’t tell him the truth because he didn’t want to get a Louisville Slugger upside the head.

So Eliot Ness and the feds got him on tax evasion. 

Richard Hatch

I wonder how the seminal Survivor winner is surviving in the hoosegow?

Hatch was convicted in 2006 of failing to report his $1 million plus winnings from the reality game show, Survivor.

Hatch’s lawyer argued that his client was just a bad bookkeeper and that he had merely forgotten to report it. Naturally, the judge didn’t buy that – how do you forget that you won a million bucks? 

Willie Nelson 

In 1990, the IRS sent Willie a bill for $16.7 million dollars in back taxes, interest and penalties. Even for someone as rich and famous as Nelson, this was a formidable debt.

Willie tried to pay the IRS back by releasing a double album titled The IRS Tapes: Who’ll Buy My Memories?

The IRS, however, got impatient waiting for the nasal nabob’s album to go Platinum so it accelerated the collection process by seizing his assets and selling them at auction.

Apparently Willie’s rich and famous pals bought most of his property and returned it to him for a nominal fee.  He was able to pay his debt to the IRS in three years.

No word on whether or not Willie used the defense that he was distracted because his gal pal, not his tax obligation, was “always on my mind.”

Update: I received a comment from  a woman named Willie’s Girl who wanted to clarify the record:

The accounting firm representing Willie made some bad investments on his behalf that were later disallowed by the IRS. Willie went on to sue the company and won his suit. He settled with the IRS for somewhere around 6 mil and paid his debt in full.

Willie invested in a bogus tax shelter and did, in fact, successfully sue his former accountant for malpractice.

Wesley Snipes

Snipes is the only African American on the list.

So much for the “it’s-because-I’m-black” defense, huh?.

Hopefully, now that Obama will be in office, these blatant and cynically bogus attempts to inject racism in defense of wrongdoing will cease.

(Then again, it’s happening in Chicago as I write this. See Bobby Rush’s comments re the Blagojevich appointment of Roland Burris to fill Obama’s Senate seat))

Snipes argued that,

[T]he indictment was “impermissibly brought on the basis of Mr. Snipes’ race” and should be “dismissed based on selective prosecution” on the ground that his two white codefendants, Douglas Rosile and Eddie Kahn, have not been charged with failure to file tax returns as Snipes has been

But Joe Kristan of Tax Updates skewered that ridiculous argument in a single paragraph,

Mr. Snipes is grasping at straws here. Rosile and Kahn are being prosecuted as the promoters of the tax evasion scheme — charges likely to lead to longer sentences — while Mr. Snipes is being prosecuted for using it. And considering how Mr. Kahn remains in custody as a flight risk while Mr. Snipes is free on bond, it’s not clear how the white guy is getting favored treatment.

The star of such scintillating works of celluloid brilliance as “White Men Can’t Jump” and “Jungle Fever”, Mr. Snipes was duped by one of those slimey tax protester lizards who will claim on your behalf (for a healthy fee, of course) that taxes are illegal and you don’t have to pay them.

Wesley is either a blatant tax cheat or he’s dumber than fans of the show Fear Factor.

Leona Helmsley

For sheer, unmitigated unlikeability, the “Queen of Mean” takes the cake hands down.

The Hotel heiress was convicted of tax evasion relating to renovations she had made on her and her husband’s $11 million home.

At trial, Helmsley’s maid quoted her as saying,

 “We don’t pay taxes. Only the little people pay taxes.”

Leona spent 18 months in jail for evading over $1 million dollars in federal taxes.

She died in August of 2007, with an estate worth over $4 billion. She gave $12 million of that to her white Maltese, Trouble.

Who is the Worst?
Al Capone
Richard Hatch
Willie Nelson
Wesley Snipes
Leona Helmsley

About Peter Pappas

Peter is a tax attorney and certified public acccountant with over 20 years experience helping taxpayers resolve their IRS and state tax problems.

He has represented thousands of taxpayers who have been experiencing difficulty dealing with the Internal Revenue Service or State tax officials.

He is a member of the American Association of Attorney-Certified Public Accountants, the Florida Bar Association and The Florida Institute of Certified Public Accountants and is admitted to practice before the United States Tax Court, the United States Supreme Court, U.S. District Courts - Middle District of Florida

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  1. Elliot Ness says:

    What a load of crap! The American government should be labeled as the biggest tax cheat, seeing as there is no official law which states that citizens must pay income tax! Wake up America. Who is cheating who?

  2. Elliot Ness,

    Income taxes are legal. Pay up or stop using the interstate highways and benefitting from national defense.


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