Apple Inc.

In 2013, Apple CEO Tim Cook stood in front of a US Senate committee and said, “We pay all the taxes we owe—every single dollar. We not only comply with the laws, but we comply with the spirit of the laws. We don’t depend on tax gimmicks.” Sure, Tim. Sure.

But whether it’s unpatriotic, disingenuous, or fair is irrelevant. The tax strategies Apple uses—primarily shifting income to Ireland—are legal. And as CEO of a public company, Tim Cook has a duty to Apple shareholders, not the US Treasury. So if he can legally save his shareholders money, he has a responsibility to do that.

Judge Learned Hand even notes in the landmark case Helvering v. Gregory that, “Any one may so arrange his affairs that his taxes shall be as low as possible; he is not bound to choose that pattern which will best pay the Treasury; there is not even a patriotic duty to increase one’s taxes.”

Now, ironically, this case created the legal doctrine known as “substance over form,” which means that you cannot just file the right paperwork to make a transaction legitimate if the underlying objective is simply tax avoidance. But so far, Apple’s strategies have held up.

Ultimately, Congress included provisions within the new Tax Cuts and Jobs Act that reduce the effectiveness of such strategies (although their success is debatable). As a result, Apple now has the coveted problem of repatriating over $250 billion in cash overseas.

Josh Norris
Bruno Bruhwiler

Bruhwiler is one of the IRS’s most recent tax protesters. In 2014, he received a notice regarding the 2011 tax year for which he had not filed a return and carried a balance of $3,840. Instead of sending a check, he took umbrage at the assertion that he owed the federal government and sent a colorful response, which listed 27 reasons to defend his position.

Some of the highlights include contentions that: he “is not a US citizen but in fact is a California National,” the IRS dealt with him as is a “fictional entity,” and “the due process of Bruno Bruhwiler has been violated and dishonored.” Obviously, the IRS did not accept his response.

So when the case went to trail in 2015, Bruhwiler got the chance to put his crazy on full display. During the proceedings, the judge asked him about income that was reported for him during the 2011 to which Bruhwiler responded, “I don’t even know what you mean by ‘income.’ I have my own definition of income.,, It’s a cat with a pink bow.” Right.

The tax court judge ruled in favor of the IRS, and although he could have been penalized up to $25,000 for frivolous proceedings, the judge showed restraint and only added a $3,500 fine to the $3,840 already due.

Josh Norris
William Koch

In 1992, when the San Diego Yacht Club won the America’s Cup, team captain Bill Koch said, “This is a triumph for America, for American technology, and American teamwork.” But the real triumph that year appeared on his personal income tax return, which included a $10 million charitable contribution toward that victory.

Funding for the whole team totaled $64 million, so not only did he get a deduction for that $10 million, but he also contributed another $44 million from foundations he controlled, which was presumably also a charitable deduction for him at some point. So why does Koch get to write off his incredibly expensive hobby and you can’t?

Fortunately for him, Section 170(c) of the Internal Revenue Code explicitly defines a charitable contribution to include organizations operated, “to foster national or international amateur sports competition,” which would include yachting. So while it may not seem fair, it’s 100% within the law. So maybe you just need to find a more expensive hobby.

Josh Norris
Roger Goodell

In 2015, the National Football League gave up its tax-exempt status, which it had held since 1966. This move seemingly should have been a watershed moment that triggered a hefty annual tax bill and negatively impacted the NFL’s finances, right? Wrong.

Most of the NFL’s income is passed on to the individual teams, leaving very little for the organization itself. So, while the NFL’s income is now taxable, there’s none remaining within the organization to tax. The teams are, of course, still highly profitable and will continue to be taxed. But little has changed for the NFL.

So why, after all this time, would the NFL give up its tax-exempt status? For one, it’s a good headline, and the NFL can use all the positive press it can get. At first glance, it appears that a large, profitable entity is voluntarily paying taxes. But as previously explained, that’s hardly the case.

But the kicker is that non-profits must report executive compensation to the IRS, which then makes that information publicly available. So while we know that Roger Goodell made $44 million in 2012 and $35 million in 2013, that information is no longer reported a private, “tax-paying” entity. Well played, Roger. Well played.

Josh Norris
Martha Stewart

You know her for cookbooks, craft making, and insider trading. But Marth Stewart has also had her fair share of tax troubles—in 2002, she was ordered to pay over $200k in back taxes and penalties to the state of New York. The dispute in question: her New York state residency.

Stewart claimed she spent little time in the state and therefore had no residency. After all, New York has extremely high state income taxes, which is why so many New Yorkers try to spend over half the year in Florida, which has no state income taxes at all.

The issue went to court, and unfortunately for her, the judge found that Stewart did not have “credible testimony.” Why you may ask? Well, apparently, she commented in one of her cookbooks about the summer home she keeps in the Hamptons, and you can’t have it both ways. So the judge ruled in favor of the State of New York.

Lying became a theme for Stewart when just two short years later in 2004, a jury found her guilty of conspiracy, obstruction of justice, and two counts of making false statements to a federal investigator in the ImClone insider trading case. Stewart famously spent five months in jail for these charges.

However, she seems to have learned her lesson and rehabilitated both her outlook and career.

Josh Norris