The long history, and future of, tax cheating

April 19, 2025

Spoiler: Tax cheating is not going away, and likely will increase thanks to recent Trump administration/DOGE actions.

Roman-fresco-man-with-papyrus-scroll_Herculaneum1AD

Roman portraiture fresco of a young man with a papyrus scroll, from Herculaneum, 1st century AD (Image by Olivierw/own work, Public Domain/Wikimedia)
   

Tax cheating is a big topic every filing season.

This year it got added attention. Many in the tax world are worried that cuts to the Internal Revenue Service by the Department of Government Efficiency (DOGE), championed by the Trump administration, will hamper the agency’s ability to effectively enforce tax laws.

But tax cheating is not new. It’s been around as long as taxes, which have been around, well, since humans created governments.

The latest example of tax cheating’s long history is a manuscript discovered in the Judean desert decades ago, but only recently analyzed. The papyrus document details, among other things, a tax-evasion scheme involved the falsification of documents and the illicit sale and manumission, or freeing, of slaves.

The illegal movers were made to avoid paying duties in the far-flung Roman provinces of Judea and Arabia, a region roughly corresponding to present-day Israel and Jordan.

The story of the ancient tax evasion effort is the first of this weekend’s Saturday Shout Outs.

New York Times reporter Franz Lidz’s article, How to Evade Taxes in Ancient Rome? A 1,900-Year-Old Papyrus Offers a Guide, explores the plot by two tax dodgers.

Lidz notes that one of the tax cheats, Gadalias, “was the impoverished son of a notary with ties to the local administrative elite. Besides convictions for extortion and counterfeiting, his catalog of misdeeds included banditry, sedition and, on four occasions, failing to show up for jury duty at the court of the Roman governor.”

His partner in crime, writes Lidz, was “a certain Saulos, his ‘friend and collaborator’ and the supposed mastermind of the caper.”

But like tax evaders across the ages, the pair was caught.

Lidz’s story looks at the discovery of 133-line historic scroll, and how following the papyrus trail led to the tale of tax fraud with the slave trade in the most remote corner of the Roman world.

It’s an ancient story that has resonated with modern tax lawyers. Lidz notes that experts said the “shenanigans of Gadalias and Saulos were not all that different from today’s most common forms of tax fraud — shifting assets, phony transactions. And the Roman interrogation methods were largely in line with Untersuchungshaft — investigative custody — for financial crimes, which involves intimidation and often brutal questioning.”

Enjoy the history and tax lesson. And take it’s lesson to heart the next time you think about trying to slip on past Uncle Sam’s modern tax collector.

And you can bet people will keep trying. That is an especially worrisome thought due to the attacks on the IRS cited earlier in this post. That’s explored in this weekend’s second Shout Out.

Trump's attacks on the IRS will encourage wealthy tax cheats, says Ryan Teague Beckwith in an opinion piece for MSNBC published on Tax Day.

“The message from Washington is clear: The IRS is on the outs,” writes Beckwith. “That may already be emboldening some would-be tax cheats as they sit down to prepare their taxes this April. And the problem will only get worse in the future.”

Beckwith also quotes former Treasury Secretary Lawrence Summers, who warned in a post on X (formerly Twitter) that tax cheating is highly contagious.

So if wealthy individuals who are able to hire knowledgeable and creative tax advisers cheat and get away with it, it’s likely that more regular taxpayers also will try questionable ways to reduce what they owe.

Most of us have already filed, and hopefully resisted the urge to cheat on our taxes.

But I agree there is a real possibility tax cheating could increase. Just how much depends on what happens to the already wounded IRS in the remainder of Trump’s second term, with assistance from Republicans on Capitol Hill who have long sought to debilitate if not eliminate the agency.

You also might find these items of interest:

 

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