Most Famous Tax Court Cases In IRS History That You Might Want to Know

Everyone wants to save money, especially when it comes to taxes. It is not illegal to reduce or minimize business or personal income taxes by legitimate accounting methods. There are, in fact, many exemptions and deductions available under state and federal tax codes to help you minimize your taxes. 

However, when you use deceptive or dishonest methods to save money on taxes, you risk facing significant penalties and perhaps jail time. Even if only a tiny fraction of returns are audited each year, the fines are not worth the risk. 

This article will introduce you to the most famous tax court cases to show how high a price you can pay for this crime.

The differences between avoiding taxes and evading taxes

There is always a clear line between the creativity in minimizing your taxes and breaking the law. Avoiding taxes is legal and understandable, but evading taxes comes with tough consequences. 

Tax avoidance means using legal accounting methods to lower the amount of taxes owed. For example, you can deposit your money into an Individual Savings Account (ISA) to avoid paying income tax on the interest you earn on your cash savings. You can also invest money into a pension scheme or claim capital allowances on things used for business purposes.

On the other hand, tax evasion occurs when a person or business uses illegal means to escape paying taxes. Some common examples of tax evasion include withholding from the IRS the tax you owe, keeping your business off the books by doing transactions in cash with no receipts, or using an offshore bank account to hide money, stocks, or other assets. 

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Most famous tax court cases in IRS history

Al Capone

Al Capone’s case is possibly the most famous one in IRS history. Though this notorious gangster had committed various illegal acts, including bootlegging, prostitution, and murder, only one landed him in prison––income tax evasion.

Under Capone’s leadership at the Chicago Outfit, the organization generated an estimated $100 million annual income. He was convicted on five counts of tax evasion from 1925 to 1927 and willful failure to file for 1928-1929. He was sentenced to 11 years in Federal Prison (including the notorious Alcatraz) and paid $80,000 in fines and outstanding tax bills.

Joe Francis

Joe Francis is a talented American entrepreneur, film producer, founder, and creator of Girls Gone Wild’s entertainment brand. He was accused of criminal tax evasion in 2007 for allegedly filing fake business tax returns. Francis is accused of submitting fake company expenses totaling more than $20 million to avoid paying taxes. He was able to avoid the felony accusation by accepting a guilty plea.

However, he didn’t seem to have completely avoided his tax problems. The IRS issued Francis a $33.8 million tax lien in November 2009.

Walter Anderson

Anderson’s case was probably one of the most famous tax court cases in IRS history. Walter Anderson, a former telecommunications executive, was accused of using aliases, offshore bank accounts, and shell businesses to conceal his earnings. Anderson pleaded a guilty plea in 2006, admitting to concealing nearly $365 million in earnings. He was condemned to nine years in prison and ordered to pay $200 million in compensation.

Anderson avoided the majority of the taxes owed due to a typo mistake in the amount of the federal government’s judgment. In this case, the IRS agreed to pay taxes and penalties for three years. Anderson is, however, still liable for $23 million owing to the District of Columbia government. 

Wesley Snipes

Wesley Snipes, the famous American actor, film producer, and martial artist, has been charged with numerous offenses by federal prosecutors. 

The “Blade” star is accused of hiding money in overseas accounts and failing to file federal tax returns for years. Snipes’ federal tax debt is reported to be approximately $12 million.

He was only convicted of misdemeanor charges in 2008 after being acquitted on felony tax fraud and conspiracy charges. 

Douglas P. Rosile, his accountant, and tax protester Eddie Ray Kahn were also accused as co-defendants. Rosile received a four-and-a-half-year sentence, and Kahn was given a ten-year sentence. 

Leona Roberts Helmsley

Leona Roberts Helmsley, an American businesswoman has accumulated a multi-billion dollar real estate portfolio. The “Queen of Mean” and her husband, Harry, were charged with invoicing millions of dollars in personal expenses as their business in order to evade taxes. Helmsley was convicted of three counts of tax evasion in 1989. She was sentenced to 18 months in federal prison. A fun fact was that she was sentenced to prison on the income tax deadline day for that year, April 15, 1992.

The bottom line

Evading taxes can lead to serious consequences. As you can see from the US’ top tax court cases listed above, it’s critical to understand what happens if you cross the line between legal tax avoidance techniques and unlawful tax evasion. If you have tax questions or have received a notice from the IRS, it’s a good idea to consult with a tax professional to discuss your situation and your choices moving forward.

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How to File for Tax Return Delays if You Can’t Meet the IRS Deadline

Picture this—you have less than three weeks to file and submit your tax return, but you’re too busy to find the time to do it. Your anxiety and stress levels increase as the tax deadline gets closer. What should you do? 

First, relax and know that you are not the only one experiencing this problem. More importantly, remember that there are ways to deal with late tax filings!

Now that you’ve calmed down, let’s tackle this together. Below, we’ve gathered the most practical solutions and tips on tax return delays so that you can prevent yourself from paying a lot of money for penalties. 

File for a tax return delay (tax extension)

If you know for sure that you won’t be able to make it by the due date, immediately file for a tax extension to avoid any possible penalties. All you need to do is fill in and submit Form 4868 to the IRS either by paper or electronically. 

However, there’s a catch. Filing an extension for tax return delays only allows you more time to file, not more time to pay your tax. In other words, if you owe money to the IRS, you have to estimate and pay at least 90% of your tax liability with your Form 4868. Otherwise, you could face a late-payment penalty. 

When is the deadline to file a tax return delay? 

The deadline to file a tax extension is the same date to file a tax return, which is April 18, 2022. An extension will delay your filing deadline to October 17, 2022. 

What happens if I don’t file a tax return delay? 

This depends on whether you owe money to the IRS or the IRS owes you money. 

  • If you have taxes to pay:

You’ll be fined 4.5-5% per month of the tax amount owed plus interest. The maximum penalty can be up to 25%. 

It’s important to remember that the penalties for failing to file a tax return or requesting a tax extension are more severe than the penalties for not paying your taxes on time (0.5%/month of the tax amount owed plus interest.)

  • If you have a refund:

You won’t suffer from penalties for not filing your tax return by the deadline, even if you don’t submit an extension. However, it might be different for state taxes. 

That being said, you still should get your taxes filed and dealt with on time. This is mainly because you must file a tax return to get your money back. 

How can I know if my tax extension is approved? 

Normally, you will receive an email from the IRS confirming within a day after you e-filed Form 4686. If you sent the tax extension request by post, you won’t receive a confirmation email and will have to call the IRS to check. Otherwise, you can just wait and see — silence means no issues most of the time. The IRS only contacts you if there’s something wrong with your extension. 

Why might my request for tax return delays be rejected? 

Though this situation doesn’t happen too often, there’s still a possibility if you don’t file Form 4686 carefully. For example, if you made spelling mistakes or provided information that doesn’t match IRS records, your request might be turned down. In this case, the IRS will normally give you a few days to correct the errors and resubmit the form. 

Another thing that could lead to rejection is unrealistic tax liability estimates. Not only will you not get an extension, but you might even be fined. 

Can I request a tax payment delay? 

Technically, yes. However, the requirements are very strict. Below is what you need to do in order to have some extra time to pay your income tax: 

  • File Form 1127 and submit it to the IRS on or before the date that the tax is due
  • Provide a complete statement of all your assets and liabilities as of the end of the last month, plus an itemized list of money you received and spent in the three months preceding submitting your request for an extension to pay.
  • Show that paying the tax by the original deadline would cause you extreme hardship (e.g., if you show it only causes inconvenience to you, there’s little chance your request will be accepted)
  • Prove that paying the tax on time would result in a significant financial loss and that you don’t have the money or can’t raise it by selling property or borrowing.

Generally, you will get a six-month extension if your request is approved. Furthermore, the IRS requires some acceptable security before issuing a payment extension. Depending on your circumstance, the security could be in the form of a bond, a notice of lien, or even a mortgage.

Extensions are sometimes granted, particularly in the event of federally declared disasters. 

Additional relief information is available on the IRS Disaster Relief page.

The bottom line 

Filing tax isn’t fun, but there are ways to make the process easier. 

Always try to file your tax return as soon as possible. In case you can’t, try to make a request for tax return delays. Remember that it will only give you more time to file your tax return, not more time to pay your taxes. 

Tax season can be very complex if you’re a business owner. Since most business-related expenses are deductible, you should go over your bookkeeping carefully to make sure you can lower your taxable income as much as possible. Having your receipts available and ready to check will put you at a significant advantage in this case.  

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Your Complete Guide to the U.S. Tax Return Definition

Tax is the money paid by citizens and businesses to the government so that they can make roads, build and maintain public parks, fund the army, provide policing, offer schooling and education, and more. 

Have you ever wondered how the U.S. government decides how much tax each individual must pay? The government’s staff don’t go knocking at everyone’s door to examine our finances and then calculate our tax duty. No, in fact, we do the job ourselves — through a tax return. 

So, what is a tax return, exactly?

This article will introduce you to the tax return definition, give an overview of its three main sections, and answer the most frequently asked questions about this financial matter. 

Tax return definition 

A tax return, also known as a tax report, is a form or a set of forms issued by the government which you fill in to report your income, expenses, and other financial information. When you complete your tax return, you’ll know if you owe any money to the government and how much to pay. In the case that you overpaid your taxes, you can also request a refund by filing the tax return. 

The tax return form for individuals for United States federal taxes is Form 1040, whereas Form 1120 is for corporations, and Form 1065 is for partnerships.

See also: What Is Tax Season And How To Prepare For Your 2022 Tax Return

The three main sections of a tax return 

Typically, a tax return consists of the following three sections: 

Income 

The income section lists all your income sources, such as wages, salaries, dividends, self-employment income, and royalties. If you’re an employee, your income will be recorded in a W-2 form provided by your employer. 

Deductions 

Deductions, also known as tax write-offs, lower your tax liability, which essentially means the more deductions you claim on your tax return, the less tax you’ll have to pay. Just be aware and make sure you only claim deductions that you’re eligible for. 

Some typical deductions for individuals that you may be able to claim are interest paid on your mortgage or your student loans, charitable donations, and contributions to your retirement saving plans. For business owners, you can claim tax deductions for most expenses involved in business operations. 

Taxpayers can either take a standard deduction or itemized deductions. For those who opt for the former method, the standard deduction for the tax year 2022 is $12,950 for single filers, $25,900 for joint filers, and $19,400 for heads of households. The deduction amount may increase slightly each year to keep up with inflation. On the other hand, if you use itemized deductions for your tax return, you choose from various individual tax deductions rather than taking a fixed deduction amount. 

Tax credits  

Many people get confused between tax deductions and tax credits, so here is the key difference: deductions are subtracted from your taxable income while credits are subtracted directly from your total tax bill. For example, a tax credit of $1,000 will result in a $1,000 reduction in your tax bill. On the other hand, a $1,000 tax deduction lowers your taxable income (the amount of money you have to pay taxes on) by $1,000. So, if you are in the 22% tax bracket, a $1,000 deduction would save you $220.

Tax credits cover a wide range of expenses and situations: you can get tax credits if you purchase solar panels for use in your home, or for child-dependent care and education credits, etc.

See more: How To File Taxes For The First Time: A Complete Guide To All Your Questions.

Who has to file a tax return? 

While most U.S. citizens and permanent residents who work in the United States need to file a tax return — not everyone must do it. Whether you have to file a tax return depends on your age, filing status, income level, and source of money.

To find out if you need to file a tax return this year, check out this detailed guideline from the IRS (Internal Revenue Service): Publication 501 (2021), Dependents, Standard Deduction, and Filing Information

What happens if I make a mistake on my tax return? 

If you filed your tax return incorrectly or failed to include something, you need to notify the IRS. To do so, you would need to file an amended return with the IRS using Form 1040-X. You can file it yourself or have a professional prepare it for you. If you don’t inform the IRS of these mistakes yourself, you could face financial penalties and pay interest. 

How can I track my refund? 

You can use the IRS Where’s My Refund? tool or call the IRS directly at 800-829-1954 to check on the status of your refund 24 hours after you e-file. The IRS will give you an exact refund date once your tax return and refund are approved.

You’ll likely receive your refunds in less than 21 days.

Final thoughts 

Understanding the definition of “tax return” and how it’s calculated will help you become more confident in dealing with this important financial process. As a result, you’ll gradually learn how to file your tax return quicker and more accurately. 

A great tip for everyone who wants to streamline their tax return filing process is to have your receipts organized. Receipts help you record transactions correctly and serve as concrete evidence for your deduction claims. It might be too much of a task to do yourself — and that’s where Shoeboxed comes in. 

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