IGNITE

Infamous Tax Criminals

by Mathew Towers

The deadline is May 1st.

We know doing your taxes can be a drag, so it’s no wonder there have been so many people who have tried to escape them throughout time. Taxes are vital to the funding of all of the infrastructure and support systems that make our community better. Without the support of taxpayers, many of the systems we rely on every day wouldn’t exist. 

To show you just how important taxes really are, we decided to compile a list of the top 5 famous tax criminals, to prove to you that not doing your taxes doesn’t pay off.

Al Capone Mugshot

Al Capone

Perhaps one of the most infamous tax evasion stories is the one of Al Capone. Reportedly linked to murder, prostitution, racketeering, and even the St Valentine’s Day Massacre, Capone was named Chicago’s public enemy number one. His tax-related conviction was ground-breaking because it ended his seemingly unbreakable control of the Chicago underworld. Al Capone received an 11 year sentence, $50,000 fine, and orders to repay $215,000 in back taxes. If this were 2017, he would be paying $700,837 and $3,000,000 respectively. While tax evasion may have seemed like a good idea at the time, it did not pay off in the long run for Capone.

Willie Nelson

Willie Nelson

In 1992, Willie Nelson owed the federal government a whopping $16.7 million dollars in back taxes and fines. In order to avoid jail time Nelson had to forfeit many of his possessions. As it turns out, his fans had his back. Quick thinking and creativity led Nelson to release the solo album “The IRS Tapes: Who Will Buy My Memories?”. Fans took the title literally and bought up his items at auction only to hand them right back over to him. Between album sales and the auction, he earned enough to clear his debt and his name, showing just how powerful music can be. But unless you’ve got a big fan base yourself, getting out of paying your taxes won’t quite so simple.

Pete Rose

Pete Rose

Pete Rose is one of the most famous players in the history of baseball, holding an astonishing number of league records, and one criminal one. Shortly after a baseball scandal left him a disgrace, Rose was charged with federal tax evasion for failing to report income from autographs, memorabilia sales, and gambling wins. Even after a guilty plea in 1990 resulted in five months in prison, it appears Rose did not learn his lesson – he was hit with a lien of nearly 1 million dollars. While today his days of tax evasion are behind him, Rose is still disgraced from baseball and considered a criminal. Tax evasion can have serious long lasting consequences for more than just your wallet – it doesn’t pay off.

Wesley Snipes

Wesley Snipes

You may know him as the vampire hunter Blade but the courts know him as a convicted tax criminal. Snipes is known for using various means to disguise exactly how large his income was, avoiding as much as $15-17 million dollars in taxes.The star was ultimately sentenced to three years in jail for tax evasion in 2010, finally released 2 weeks before taxes were due in 2013. No matter what extreme means you go employ to disguise your tax evasion, Snipes is the evidence that it is not worth it.

Martha Stewart

Martha Stewart

Martha Stewart is a lot of things – celebrity, home and garden guru, and convicted tax evader. Many of us know that Stewart did jail time for insider trading, but before her conviction she was also caught on tax evasion charges. The state of New York forced her to pay a whopping $220,000 in back taxes/penalties. It looks like Martha learned the hard way that even mansions generate taxes.


Clearly not doing your taxes is not a good idea. IGNITE wants to make sure you’re covered. Our Tax Clinic runs March 21st to April 21st on weekdays from 10 a.m. to 4 p.m. Book an appointment and get your taxes done for free at North or Lakeshore!

Be sure to keep an eye on our Upcoming Events to make the most of your student experience!