Cat food, death, and heavy machinery: Learn about loopholes in the American tax code

Read why the information Americans have about our tax system might be misleading

For many, filing taxes can be complicated and overwhelming. Some argue that the tax system obscures certain aspects of the US tax code, making it difficult for taxpayers to accurately assess potential reforms.

Watch a breakdown of tax breaks most Americans don't know about

Programs like healthcare savings accounts or flexible spending accounts are tax-free accounts that are designed to help lower healthcare costs. However, many Americans don't use them and don't understand how they work.

Tax-loss harvesting is a way that some people attempt to trim their tax bills

Specifically, tax-loss harvesting is a way to lower your tax bill by offsetting investment gains with losses. It can be tricky to practice and comes with a few important rules, so working with an expert may be your best bet before Tax Day.

Watch what happens if you commit tax evasion, from phone calls to property seizure

Tax Day is one of the most dreaded days for working Americans. The IRS responds differently to late filings and late payments. If you don't file at all, the IRS might freeze your assets.

Gifting money is one way to avoid death taxes

Gifting money while you're alive is one way people avoid estate and inheritance taxes. There is a yearly cap on how much you can give to a person before that money is taxed—but there isn't a cap on how many people you can give money to in a year.

The 'playing card' and 'blueberry' taxes are among the strangest around the world

In Canada, companies making children’s breakfast cereals are granted a tax exemption if their cereal boxes contain free toys. While the exemption is limited to toys that are not “beer, liquor, or wine,” the cereal tax is far from the world's most eccentric tax.

If the estate tax is repealed, more expensive alternatives might come in its place

The federal estate tax has been up for political debate for decades. Many want to get rid of it altogether. If repealed other tax options, like capital gains taxes, could have people paying more in taxes than before.

In 1931-32, JP Morgan Jr. paid no income taxes due to his company’s losses

This legally reduced his taxable income under existing laws. Similarly, the Rockefellers leveraged charitable foundations to minimize taxes, allowing them to preserve wealth while directing funds to their preferred causes.

How tax laws helped the federal government catch mob bosses during Prohibition

The IRS arrested top mob bosses during Prohibition after the Supreme Court ruled illegally-made income could be taxed. The IRS's biggest catch was Al Capone, who was charged with tax evasion and sentenced to 11 years in prison. But Capone wasn't the only bootlegger the IRS nabbed for tax evasion during this era.

Mutual funds and taxes

With mutual funds, you can expect a similar tax experience to that of bonds and stocks, although there are a few key differences. Look out for potential taxes on any capital gains or dividend earnings.

The story of a bitcoin loophole that gave one man millions

James Parker discovered a glitch in an Australian cryptocurrency exchange that would allow him to cash in credits worth over $20M and make big gifts to his friends. Like most loopholes, the authorities found out, but not before his life was transformed. The first in a six-part series.

The de minimis exemption was a US tariff loophole

Until Aug. 29, 2025, US consumers could purchase up to $800 of goods per day, directly from an overseas company without incurring any tariffs on the products.

Read about 'skiplagging,' a money-saving travel hack

A consumer loophole known as "skiplagging" is a travel hack where travelers purchase a cheaper flight with a layover in their destination city. The hack works when flights to other cities with layovers at your destination are cheaper than direct flights to your destination. Airlines don't like the practice, but there's no specific law forbidding it.

Paperwork errors cost families millions in life-insurance payouts

This podcast episode reveals how human missteps by employers and insurance providers caused hundreds of families who paid life-insurance premiums to be denied millions of dollars in death benefits. A Wall Street Journal reporter breaks down how flaws in the system made this happen.

The complicated economics of horse racing

The Triple Crown commands big ratings (and enormous amounts of money in betting) but the sport as a whole is in a precarious position, thanks to limited tracks and an overreliance on subsidies. This special from Freakonomics unpacks what all that means for the future of the sport.

A brief explainer on food expiration dates and what they really mean

Roughly 20% of food items in the US are thrown out because consumers don't understand how to interpret expiration labels. Over time, when supermarkets began carrying processed foods, grocers use packaging codes to track how long foods had been on...

Backdoor Roth IRAs are loopholes used to access the tax advantages of a Roth IRA for individuals who otherwise make too much money to qualify for one

Backdoor IRAs work by investing money into a traditional IRA, and then converting that traditional IRA to a Roth IRA.

Rat taxidermy can be a tender, if unsettling, communal activity

At a rat taxidermy class in Chicago, participants use previously deceased rats, usually from lab experiments, as they learn the art of preservation step-by-step. Despite the gore, the act can engender tenderness toward the animal and prompt healthy reflection on death and dignity.

A taxonomy of restaurant types

What's the difference between "fast food" and "fast casual"? Is there any real difference between a "diner" and a "family style restaurant"? This guide from DoorDash explores the industry's fine distinctions, along with some deeper dives into specific enterprises that found success.

A Missouri farmer sold $140M worth of fake organic feed

Randy Constant sold nonorganic feed to other farmers, who fed it to their animals, which were then sold as organic meat. The scheme began sometime in the mid-2000s and ended after a tip, likely from one of Constant’s competitors, to the US Department of Agriculture. Constant pleaded guilty and was sentenced to 10 years in prison, but died by suicide before serving time.

Wealthy Americans are keeping car dealerships afloat

In the past five years, the share of people buying cars above $50K has increased by several-fold. Car prices have significantly increased overall in recent years.

Your pet might eat you if you die

Cats and dogs can eat their deceased owners. Experts say it typically occurs after days without food and reflects basic survival instincts, rather than aggression, affection loss, or a sudden behavioral shift.

Ridiculous documents released via the Freedom of Information Act

In addition to being a massive asset to journalists and eager members of the public, FOIA has also shed light on some of the weirder corners of America’s functioning democracy. Here are 10 choice documents.

Explore the gap in what Americans die from versus news coverage on death causes

Top killers like heart disease, stroke, and liver disease, though they represent a significant burden nationally, are not often extensively covered in the media.

All-you-can-eat buffets are a practical demonstration of economic ideas

Economists have noticed some restaurant goers prefer a flat pricing model despite it usually being more expensive than per-dish costs. The strategy behind endless servings includes concepts such as economy of scale, cross-subsidization, diminishing returns (of enjoyment of excess food), and more.

Larger animals like giraffes, elephants, and blue whales have developed a unique defense against cancer, a phenomenon known as Peto's Paradox

Calculate how much of your tax dollars go to each federal program based on your income, filing status, and number of children

When you complete a CAPTCHA on a website to prove you are human, you may be unknowingly training algorithms for self-driving cars, whose systems require training data to help identify crosswalks, bicycles, and other outdoor objects.

Explore fun facts from the USPS, including unique post office buildings, a stamp that traveled past Pluto, and more.

Hedge funds, the private investment firms that trade a wide swath of financial assets, make money by imposing steep fees on investors and from the fund's investment performance.

At the beginning of the 20th century, a group of young men ate standard American food—replete with food additives like borax and formaldehyde—as part of government research to better understand food safety.

Gerrymandering works through two techniques: cracking opposing voters across districts to dilute their power, and packing them into a few to waste their votes in lopsided majorities.

Art theft is the third-largest source of criminal revenues worldwide, thanks in part to the subjective nature of valuing a work of art.

US consumers collectively owe more than $1T to credit card companies—almost as much as they owe in auto loans.

Louisiana's 'Cancer Alley' is infamous for having some of the highest industrial pollution, toxic air emissions, and cancer risks in the US.

Netflix profits when you're not watching, and its movies are designed that way—read a detail-rich critical essay exposing lesser-known Netflix takes

Discover the catastrophic consequences of a failure of the US electrical grid—something that is more likely than many Americans think.

Despite being favored by 87% of Americans, Congress does not have term limits.

See these 16 pieces of art evoking phobias of snakes, flying, spiders, and more. 

Up to a million Girl Scouts sell about 200 million cookie boxes every spring, generating $800 million, largely because refusing a child is frowned upon

A vending machine run with Anthropic's AI went out of business after it was convinced to give away items for free and sell a video game console.

A Yale student wrote a profound essay about the consulting industry's influence on elite college students that was published in a book of her writing after she died in a post-graduation car accident.

Massive 3D printers have been used to build homes by stacking layers of 'concrete toothpaste,' a fire-resistant material that effectively insulates against outside noise.

SpongeBob exemplifies Aristotle's philosophy for living well because he understands that happiness doesn't come from external factors like money, recognition, or power.

See this overview of the firework rules across all 50 states, ranging from a complete ban on non-professional fireworks in Massachusetts to states with more lax rules like Indiana.

Search a massive database of over 4 decades of clues from the TV quiz show 'Jeopardy!'

Hear 50 years of iconic hip-hop samples, the genre's foundational looped tracks

Watch how deep-sea mining equipment collects and processes polymetallic nodules—metal-rich, potato-shaped rocks—from the ocean floor and creates environmentally damaging plumes of sediments.

In 1939, baseball star Lou Gehrig delivered his inspirational 'Luckiest Man' speech after retiring due to the health condition that now bears his name.

The Ramones' 'Pet Sematary,' the theme song for the Stephen King novel of the same name, was written while the band was admiring the writer's collection of horror memorabilia.