Roni Deutch Discusses the 10 Biggest Tax Evaders in US History

Roni Deutch Discusses the 10 Biggest Tax Evaders in US History

10) Sunny Garcia

Famed surfer Sunny Garcia won numerous world surfing championships and starred in numerous television shows before he was found guilty of tax evasion. Garcia was only the second surfer in the world to win a prize of over million, and also earned hundreds of thousands of dollars in other prizes and endorsements. Unfortunately Garcia neglected to pay income taxes to the U.S. government on any of the prize money he received from competitions outside the U.S.

9) Richard Hatch

Most people recognize Richard Hatch as the winner of the first season of Survivor, where he won a million prize. Unfortunately he never paid federal income taxes on that million, or money he was paid for professional appearances totaling nearly 0,000. U.S. prosecutors reportedly offered Hatch an arrangement where he could received a lenient sentence in exchange for a guilty plea. However, he refused this offer claiming that CBS had offered to pay taxes on his prize money. Hatch later acknowledged he was entirely incorrect. In May 2006, he was sentenced for 51 months in prison, and three years of supervised release afterwards.

Edward and Elaine Brown

In January of 2007, a jury found Edward Brown guilty of three federal counts of tax evasion, and a few weeks later his wife Elaine was found guilty on seventeen tax fraud related charges. Combined, the two failed to report over million in taxable income and were each sentenced to five years in prison. The Browns claim they were not shown any legitimate law that required them to pay taxes, therefore they felt they should not be forced to pay.

7) Harry Eugene Claiborne

Claiborne, a United States District Court judge, was found guilty of tax evasion in 1984. He was born in Arkansas and unsuccessfully ran for a seat in the U.S. Senate before President Jimmy Carter appointed him to the District Court of Nevada. Claiborne was indicted for bribery, fraud, and tax evasion by a federal grand jury in 1983. He was tried for all three counts by the federal government in a case that was declared a mistrial. Later, he was tried on just the counts of tax evasion and was found guilty. He was sentenced to two years in prison.

6) Tom Coughlin

Coughlin served as the vice-chairman of Wal-Mart Stores, Inc. and was a close friend of founder Sam Walton until he was convicted of tax evasion, embezzlement, and theft. According to Coughlin, the money he stole from Wal-Mart was to pay bribes to union officials to not organize at Wal-Mart locations. However, U.S. attorneys could not find any evidence to support Coughlin’s claims. Coughlin pled guilty in 2006 to five counts of wire fraud and one count of tax evasion. He was sentenced to 33 months of in-home detention and forced to pay over 0,000 in restitution to Wal-Mart Stores Inc. and the Internal Revenue Service.

5) Al Capone

Capone, known frequently as “Scarface”, was an Italian-American gangster who profited off the illegal bottling and distribution of alcohol during the prohibition. Although he was placed on the Chicago Crime Commission’s “public enemies” list he was never successfully convicted of any racketeering charges. However, his criminal career came to an end in 1931 when he was convicted and found guilty of income tax evasion. Capone was sentenced to eleven years in a federal prison, one year in a county jail, and an ,000 fine. Fortunately his legal representatives paid all of Capone’s past due taxes.

4) Pete Rose

On April 22, 1990, baseball superstar Pete Rose pled guilty to two charges of tax evasion. Rose was a player and manager in Major League Baseball, and was best known for playing for the Cincinnati Reds. As part of his plea, Rose admitted to filling false income tax returns that did not show income from selling autographs, memorabilia, and gambling winnings. Rose was sentenced to five months in prison at the medium security prison camp in the United State Penitentiary in Marion, IL. He was also fined ,000 and forced to pay the Internal Revenue Service over 0,000 in back taxes and interest. Rose paid his fines and was released from prison in January 1991.

3) Reuben Sturman

Sturman ran one of the most successful pornography operations in U.S. history before finding himself in trouble with the IRS. Based in Ohio, he ran numerous businesses that generated an estimated 0 million in just the year 1991. Sturman faced numerous legal charges dating back to 1964, but always avoided prosecution by counter-suits, shady business dealings, and using multiple aliases.

Because of how Sturman hid his assets he, along with five associates, were indicted of tax evasion by the federal government. In 1989, he was convicted and sentenced to ten years in jail. He was also ordered to pay the IRS over .5 million in unpaid taxes and fees. A few months later, Sturman was charged for transporting obscene material. The case was expected to end in a plea bargain, but during the case Sturman was caught trying to bribe a juror. As a result he was charged with extortion and sentenced to nineteen additional years in prison.

2) Wesley Snipes

In October of 2006, actor Wesley Snipes was indicted for committing tax fraud against the federal government. He was accused of owing the federal government over million in unpaid taxes and failing to file tax returns for over six years. In 1997, Snipes tax return reported his adjusted income as , when according to the government his income was over million.

1) Walter Anderson

On February 26th, 2005 the Justice Department arrested Walter Anderson in the largest tax evasion case in U.S. History. Anderson was accused of hiding income and assets by setting-up offshore companies in Panama and the British Virgin Islands. These companies reportedly generated over 0 million in revenue during a five-year period.

Anderson pled guilty to two felony counts of tax evasion and one felony count of defrauding the District of Columbia. He admitted to hiding 5 million in income and was sentenced to nine years in prison. He was also ordered to pay 0 million to the government. However, that figured was later dropped to million by a federal district judge.

Prior Year Tax Preparation Online

The Biggest Mistake With C Corporations and How to Save Taxes Using the C Corporation Double Tax

The Biggest Mistake With C Corporations and How to Save Taxes Using the C Corporation Double Tax

When used correctly, C Corporations are a great way to supercharge a tax strategy. I find that when my clients make the most of their C Corporations, they reduce their taxes by a minimum of ,000 every year.

- The Biggest Mistake With C Corporations -

The key to saving ,000 in taxes every year is knowing how to use a C Corporation correctly. When I meet with prospects and review their prior year tax returns, it’s not unusual that I find a C Corporation that isn’t being used correctly. In these cases, the C Corporation is not saving any taxes and in some cases it is actually creating more taxes! So what makes these C Corporations not work? These C Corporations do not save taxes because the wrong type of business is in the C Corporation.

Only certain types of businesses will generate tax savings by operating as a C Corporation. The type of business that does work is what I refer to as a support business or a secondary business. Now, you may be wondering, what is a support or a secondary business? Sometimes it’s easier to define what it isn’t.

The Types of Businesses That Don’t Save Taxes in a C Corporation:

Primary Operating Business. This is a business that creates the main source of cash flow for the owner. The owner relies on this cash flow for living and other personal expenses. The primary operating business is how the owner makes a living. In this type of business, it is critical that the owner be able to get cash out of the company in a very tax efficient way. While it is possible to get cash out of a C Corporation, it becomes inefficient from a tax standpoint to do so with large amounts of cash. Bottom line: if you rely on the cash from your business to pay for your living expenses, that business is not ideal for a C Corporation.

Investment or Rental Real Estate Business. There are several reasons why this type of business doesn’t work in a C Corporation. I’ll share the top two reasons.

First, this type of business involves assets that appreciate. C Corporations do not have a “special” lower tax rate for capital gains (which are generated from appreciated assets). Individuals do have a special capital gains rate so that benefit is completely lost in a C Corporation.

Second, the income generated from these investments is often subject to a special (additional) tax in C Corporations called a personal holding company tax. This tax only applies to this type of income and only in a C Corporation. The tax effectively eliminates the lower tax rates that a C Corporation normally has. This tax was specifically put in place to keep taxpayers from putting investment assets in a C Corporation as a way to pay less tax on their investment income.

The Type of Business That DOES Save Taxes in a C Corporation:

Now that we have eliminated primary operating businesses and investment businesses from the types of businesses that do not save taxes in a C Corporation, what is left? What is left is secondary or support businesses. These are best defined as businesses that generate a modest amount of profit (no more than ,000 annually) and the cash flow that is generated is not needed by the owner to pay for living or personal expenses.

By far the biggest objection I hear anytime I bring up a C Corporation is…

But What About the Double Tax? Sometimes just the mere thought of paying a double tax sends people running in fear. Fortunately, I’m not afraid of the double tax and I actually have a strategy where the double tax can work to reduce my clients’ taxes.

What Is the Double Tax? The double tax is this:

First tax: A C Corporation pays its own tax on its net income. This is the first tax.

This is a great tax reduction strategy! Because a C Corporation pays its own tax, it has its own tax rules and you can legally use these rules to reduce your taxes.

Second tax: A C Corporation can use the cash it has after paying its own tax to pay dividends to its owners. When a C Corporation pays dividends to its owners, the owners pay tax on that dividend. This is the second tax.

At first glance, which is usually the only look most people (including CPAs) give a C Corporation, it seems that the double tax is the worst case scenario when it comes to tax planning. So many are surprised when I share this:

It Is Possible to Pay Less in Tax Even With a Double Tax!

Let’s take a look at how the C Corporation double tax can play out:

First tax = 15% A C Corporation pays 15% tax if it has net income of ,000 or less.

Second tax = 15% An individual pays 15% tax on dividends.

Total double tax = 30% (The double tax can end up being a little less than 30% but to keep things simple for this example, 30% will be used).

This means if an individual is in a 35% tax bracket, it is possible to pay less tax by incurring a double tax that totals 30%!

Prepare Prior Year Taxes Now

The Biggest Mistake With C Corporations and How to Save Taxes Using the C Corporation Double Tax

- The Biggest Mistake With C Corporations -

The key to saving $10,000 in taxes every year is knowing how to use a C Corporation correctly. When I meet with prospects and review their prior year tax returns, it’s not unusual that I find a C Corporation that isn’t being used correctly. In these cases, the C Corporation is not saving any taxes and in some cases it is actually creating more taxes! So what makes these C Corporations not work? These C Corporations do not save taxes because the wrong type of business is in the C Corporation.

Only certain types of businesses will generate tax savings by operating as a C Corporation. The type of business that does work is what I refer to as a support business or a secondary business. Now, you may be wondering, what is a support or a secondary business? Sometimes it’s easier to define what it isn’t.

The Types of Businesses That Don’t Save Taxes in a C Corporation:

Primary Operating Business. This is a business that creates the main source of cash flow for the owner. The owner relies on this cash flow for living and other personal expenses. The primary operating business is how the owner makes a living. In this type of business, it is critical that the owner be able to get cash out of the company in a very tax efficient way. While it is possible to get cash out of a C Corporation, it becomes inefficient from a tax standpoint to do so with large amounts of cash. Bottom line: if you rely on the cash from your business to pay for your living expenses, that business is not ideal for a C Corporation.

Investment or Rental Real Estate Business. There are several reasons why this type of business doesn’t work in a C Corporation. I’ll share the top two reasons.

First, this type of business involves assets that appreciate. C Corporations do not have a “special” lower tax rate for capital gains (which are generated from appreciated assets). Individuals do have a special capital gains rate so that benefit is completely lost in a C Corporation.

Second, the income generated from these investments is often subject to a special (additional) tax in C Corporations called a personal holding company tax. This tax only applies to this type of income and only in a C Corporation. The tax effectively eliminates the lower tax rates that a C Corporation normally has. This tax was specifically put in place to keep taxpayers from putting investment assets in a C Corporation as a way to pay less tax on their investment income.

The Type of Business That DOES Save Taxes in a C Corporation:

Now that we have eliminated primary operating businesses and investment businesses from the types of businesses that do not save taxes in a C Corporation, what is left? What is left is secondary or support businesses. These are best defined as businesses that generate a modest amount of profit (no more than $75,000 annually) and the cash flow that is generated is not needed by the owner to pay for living or personal expenses.

By far the biggest objection I hear anytime I bring up a C Corporation is…

But What About the Double Tax? Sometimes just the mere thought of paying a double tax sends people running in fear. Fortunately, I’m not afraid of the double tax and I actually have a strategy where the double tax can work to reduce my clients’ taxes.

What Is the Double Tax? The double tax is this:

First tax: A C Corporation pays its own tax on its net income. This is the first tax.

This is a great tax reduction strategy! Because a C Corporation pays its own tax, it has its own tax rules and you can legally use these rules to reduce your taxes.

Second tax: A C Corporation can use the cash it has after paying its own tax to pay dividends to its owners. When a C Corporation pays dividends to its owners, the owners pay tax on that dividend. This is the second tax.

At first glance, which is usually the only look most people (including CPAs) give a C Corporation, it seems that the double tax is the worst case scenario when it comes to tax planning. So many are surprised when I share this:

It Is Possible to Pay Less in Tax Even With a Double Tax!

Let’s take a look at how the C Corporation double tax can play out:

First tax = 15% A C Corporation pays 15% tax if it has net income of $50,000 or less.

Second tax = 15% An individual pays 15% tax on dividends.

Total double tax = 30% (The double tax can end up being a little less than 30% but to keep things simple for this example, 30% will be used).

This means if an individual is in a 35% tax bracket, it is possible to pay less tax by incurring a double tax that totals 30%!