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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Do you pay virtual currency tax in the US?

Yes! If you live in the U.S. and are involved in trading or investing in cryptocurrencies, any income you gain, known as capital gains, are subject to virtual currency tax. 

Virtual currencies, such as cryptocurrencies, have similar value to real currencies.

This article explains  virtual currency, its tax consequences, and where to get more information. 

According to the IRS – “Virtual currency transactions are taxable by law just like transactions involving any other property. Taxpayers transacting in virtual currency may have to report those transactions on their tax returns.” 

Virtual currency – Definition and tax consequences 

What is virtual currency? 

A virtual currency is a digital representation of value that serves as a means of trade, a unit of account, and a store of value. It functions in some situations like “real” currency (i.e., U.S. or foreign coin and paper money designated as legal tender, circulates, and is commonly used and recognized as a medium of exchange in the country of issuance). Still, it does not have legal tender status in the U.S. Cryptocurrency is a virtual currency that uses cryptography to validate and protect transactions on a distributed ledger, such as a blockchain.

Virtual currencies, such as cryptocurrencies, have similar value to real currencies. It can serve as a substitute for real currency, also known as “convertible” virtual currency. For instance, bitcoin owners can digitally trade coins between users. Owners can also purchase coins using any currency or exchange them into different currencies, such as U.S. dollars or Euros. 

What are the virtual currency tax consequences? 

Any action involved in the selling, trading, or exchanging of virtual currencies to pay for goods or services and investments may result in tax liability. 

The Internal Revenue Service (IRS) issued IRS Notice 2014-21, IRB 2014-16, providing guidance for individuals and corporations on the tax treatment of virtual currency transactions.

Individuals who have bitcoin as a capital asset but are not in the trade or business of selling cryptocurrency might find answers in the IRS’s Frequently Asked Questions on Virtual Currency Transactions.

Where to get more reliable information? 

You can access the IRS website on virtual currency to find the latest information. On the website, you’d be able to find frequently asked questions and related documents on virtual currency and taxes. 

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Let us know if you are interested in reading more about cryptocurrency! Please share your thoughts with us in the comment section! 

Does The IRS Accept Receipt Scan for Tax Deductions?

As the 2021 tax season comes to an end, the stress is starting to creep up on business owners. Preparations can be taxing on business owners, often involving numerous steps. This includes double-checking accounting records, going over their tax claims to make sure the final numbers are correct, and sorting through piles of receipts that they’ve hung onto to submit to the IRS. If you’re looking to streamline this process by digitizing your receipts, you may be wondering—does the IRS accept your receipt scans? can receipt scans legally support your tax write-offs the same as original paper receipts? 

We are here to put your mind at ease. 

The short answer to your worries is yes. Receipt scans are 100% legitimate and approved by the IRS. In fact, the IRS has accepted scanned and digitized receipts as valid tax records for tax purposes since 1997! As such, scanned receipts must meet certain requirements in order to be eligible. 

Read on to find out if your receipt scans have met all of the IRS’s requirements. 

What are the requirements for a receipt scan to be accepted by the IRS?  

According to the IRS, digital or scanned receipts must meet the following requirements:

  • Receipt scans are completely identical to their original versions.
  • Each receipt scan must exhibit a high degree of legibility and readability. 
  • You must be able to provide hard copies of the scanned receipts in the event of an IRS audit.
  • Scanned documents must be stored in a secure place.

If you can ensure your scanned receipts are properly stored and backed up, and you can reproduce hard copies from them in a legible, readable format, you may dispose of the original receipts. 

You might also be interested in: Understanding the IRS’s Tax Underpayment Penalty and How to Avoid It.

What is the most effective way to scan your receipts? 

If you’re looking for an easy and convenient way to scan your receipts, Shoeboxed is what you need. Since 2007, Shoeboxed has helped many accountants, freelancers, and businesses scan, digitize and store their receipts safely in the cloud. Simply scan your receipts with your phone with just a click, and perfect digital versions of your paper receipts will appear in your Shoeboxed app!

On top of that, Shoeboxed automatically extracts, categorizes, and human-verifies important data from your receipts so that you can go over and check your records anytime with ease. 

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