Should You Not File Taxes Until 2020?

Some things to consider

Eric Howerton
The Poleax
15 min readApr 17, 2017

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Photo by Max Goldberg

During the 2016 Presidential debates in Washington, DC, Donald Trump responded to Hillary Rodham Clinton’s accusation that he does not pay federal income taxes with four simple words: “That makes me smart.”

If you find Trump’s equation of tax avoidance and intelligence a dubious claim, you’re not alone. Over the past three months, Trump has supplied the American public with so many gaffs that, for the first time in recent memory, the round-the-clock news cycle can’t keep pace and seems a loss for how to cover those gaffs. Whether it’s Trump’s ostensible ignorance of history (e.g. Frederick Douglass’s life — and death — over 100 years ago), his willful reporting of verifiably false information (e.g. the size of Trump’s inauguration turnout and Electoral College margins, his outlandish claims (e.g. “drugs are cheaper than candy bars”), or his grossly underestimated staffing and management of the executive branch, very little about what Trump says or does gives rise to the belief that his IQ is even one point beyond the mean. And anyhow, belligerently shouting “I’m smart!” without provocation is a surefire way of casting doubt on whether this boast carries any merit.

All of which is to say that not paying your taxes doesn’t make you a cognitively superior being. It can, however, make you a criminal.

Take, for instance, Al Capone. Though most recognizable as an icon of organized crime and bootlegging, the original Scarface was imprisoned for seven years not for his violence and smuggling but for failing to report and pay tax liability on illegally acquired income.

Like Trump, Capone intensely disliked contributing a percentage of his empire’s earnings into the common pot. But the similarities don’t stop with a reluctance to help pave our streets or pay our teachers’ salaries. Capone, like Trump, hailed from New York, enjoyed vacationing in Florida, profited from gambling, was known to be a bullish instigator and provocateur of violence, and garnered public support as a populist while downplaying his own execrableness and profligacy. There has also been some speculation of late as to Trump’s mental fitness (dementia and senility have been suggested as possible causes for his more erratic behavior), and Capone too suffered from recognizably diminished capacities toward the end of his life as untreated syphilis gnawed at his brain.

If you’re anything like me, the prospect of paying taxes to a government run by a man who so resembles a notorious gangster — and has contempt for the act of paying one’s fair share as well as purports the stupidity of those who do — sticks in your craw like gum in hair. As we creep ever closer to the filing deadline, I cringe knowing the distribution of this year’s tax dollars will be largely determined by Trump. The budget he’s proposed is an insult to those supported by social welfare programs and protected by environmental and industry regulations. While I can’t say I’ve ever enjoyed filing my taxes, never once have I debated whether paying taxes was something I could or should avoid . . . until now.

With the man helming the government claiming that not paying taxes is a “smart move,” I began asking myself why I was paying my taxes like a sucker and if I could take a page from the Trump playbook. Was there, I wondered, a way to keep my hard-earned money out of Trump’s small hands so that he can’t hand it over to corporations with already-big pockets.

Is it a crime not to file a tax return?

A quick Google search of “Is it a crime not to file a tax return?” revealed that not doing so is usually a civil offense, though it can, in some instances, become a criminal one.

From here my mind took off and a sense of euphoric freedom soon followed. In my haste, I became convinced that I could elect not to file a tax return for the duration of the Trump administration so long as I filed late (hopefully after only four years) and willingly incurred what I assumed would be minor fines. Given the fact that not filing a return did not generally constitute a crime, I was willing to engage in a civil violation if it meant sleeping more easily at night.

Much to my dismay, though, I soon realized my plan wouldn’t really keep money away from the Trump administration, at least not in the way I had envisioned. Since the age of 16, I have filed tax returns every year, and for the overwhelming majority of those years I received a small refund. Only during the years when I worked contract jobs (where I was paid in bulk amounts with no withholding) did I ever owe anything to the government. This meant that in refusing to file a 2016 return I was, in essence, opting not to collect a much-needed refund and, in so doing, actively undermining my own agenda by foolishly surrendering to the Trumpian hooligans the portion of my income that should rightfully return to me. In essence, I was giving Trump an interest-free loan — a thing he’s probably used to as a result of stiffing his contractors.

In retrospect, I should have figured that, though. If I was owed money, of course the IRS wouldn’t come looking to hand it back. But I wasn’t yet ready to admit defeat.

Thinking like Trump

Maybe in order to beat Trump, I’d have to think like him. Embrace his demons. So I took a dollar bill out of my wallet and stared at if for a full five minutes. Nothing stirred in me. Then, risking disease, I touched my tongue to the dollar bill to taste it. Still nothing. Then, risking decency, I thought about touching myself with the dollar bill.

Thankfully, an idea intervened.

In order to keep as much money away from Donald Trump as humanly possible, I would have to increase the number of allowances I claimed on my W-2 Form so that no taxes would be taken out by my employer. This course of action, in combination with not filing future returns until Trump was out of office, would mean that the entirety of my salary would be paid directly to me, at which point I would hold the taxable portion hostage. In order to show good faith in actually paying this money back, I’d create an escrow account where I could deposit between 15 and 20 percent of my paycheck in order to cover the cost of repayment. When Trump left office, I’d retroactively file my taxes for the years skipped and pay the incurred penalties, which I told myself were simply the government’s way of discouraging my protest and should not dissuade me from action.

I did have some questions about my W-2, as claiming more exemptions seemed somewhat more suspicious and deliberate than simply “forgetting” to file a return for the next four years. So I contacted Samuel Brunson, professor of law and tax scholar at Loyola University of Chicago. After hearing the details, he immediately dubbed the entire affair “illegal” and informed me that the penalties for not filing a return were more than “discouraging.” In addition to hefty fines, my uncollected tax liability would collect three percent interest per month until it was paid off in full. If you have the money to afford it and want to make a point, maybe this is for you, but for most of us, it’s not going to happen. So much for that.

A brief history of conscientious tax resistors

Still, Professor Brunson did assuage my frustrations by informing me that I wasn’t alone in my quest for dissent. As I delved into the complicated history and nuance of tax evasion, tax avoidance, and tax resistance (each different in definition and degree of legality), one thing came to light: the history of American tax resistance is populated with fascinating figures who’ve gained notoriety for refusing to pay taxes not because they wanted a little extra change jingling in their pockets (as Trump has more or less admitted) but either because they objected to funding specific government activities or because they believed the language of the constitution itself forbade a permanent and compulsory system of taxation.

Vivien Kellems

Photo by Blank & Stoller from the Smithsonian Archives

Very few tax resisters — at least on the surface — appear motivated by anything resembling a fetishistic desire to stockpile excess capital. Vivien Kellems (1896–1975) at first bears a superficial resemblance to Trump — an avowed capitalist, millionaire, and business owner. Yet Kellems resisted the overreach of the federal government by refusing to withhold income tax from her employees’ paychecks. Kellems’s argument, which did not hold up in court, was that by obliging her to calculate, withhold, and deliver employees’ tax liability, federal and state governments were, in fact, forcing her to act as the government’s proxy. Kellems refused to be an unwilling and uncompensated tax collector, and it landed her in court several times.

However, Kellems wasn’t afraid of the government and she wasn’t afraid of the courts. Outspoken and bold, she appeared on Meet the Press in 1948 to speak on behalf of her tax resistance. She pulled no punches and spoke with conviction: “If [the federal government] wanted me to be their agent,” she said, “they’d have to pay me, and I want a badge.”

Though Kellems was somewhat successful in her tax resistance — she won the occasional court case and managed to stay out of prison for her evasions — , the government made sure it got its money in the end. Not only were taxes ultimately collected from Kellems’s employees, but shortly after her death, the government slapped her estate with a bill for nearly $265,000 in back taxes. Much as Kellems may have passed believing she left behind an admirable legacy of tax protest, the federal government succeeded in driving home the message that taxes, with death, were one of life’s few certainties.

Irwin Schiff

Other tax resisters, like Irwin Schiff (1928–2015), were regularly jailed for their efforts to defy what many regard as settled law. Carrying a huckster’s air not completely unlike that of Trump, Schiff presented his counter-arguments in book form and build a business hawking his ideas to the like-minded. Yet unlike Trump, Schiff appeared to have robust ideological reasons for his tax non-compliance: he held that a close reading of the constitution made it abundantly clear that the manner in which the tax code was applied made the process and the penalties illegitimate. Some of Schiff’s more novel interpretations of the law led him to believe that — because “salary” and “income” were not equivalent terms at the time of the constitution’s drafting — the 16th Amendment only granted Congress the power to collect taxes from businesses, not from individuals.

Of course, as you may have guessed, none of Schiff’s arguments hold any water when scrutinized by a legal expert. Professor Brunson noted that Schiff’s arguments are “particularly stupid” and, well, “bad.”

While Schiff’s arguments about the differences between “salary” and “income” can now be chalked up to splitting hairs, some of his other arguments are engaging as philosophical exercises, but not as legitimate tax avoidance strategies. For example, Schiff argued that that the rights afforded us in the Fifth Amendment (which protects individuals from self-incrimination) are violated whenever the government requires its citizens to provide a detailed disclosure of annual financial earnings. (Brunson clarified that, for most tax filers, a tax return is not an admission of guilt and therefore is not subject to Fifth Amendment protections.) If these documents can later be used to leverage penalties or criminal sanctions, Schiff argued, citizens who are compelled to provide them to the government have become victims of a civil rights violation.

Constitution of the United States

Schiff’s most legitimate-sounding (though, again, legally unsound) anti-tax jeremiad comes in the form of challenging the government’s use of an oxymoronic phrase, “voluntary compliance,” which litters a number of official federal documents. In his text The Federal Mafia (1992), Schiff dubs the term “propaganda,” describing its very ambiguity as a thinly veiled brainwashing technique meant to convince a naïve public that filing a tax return is mandatory when — according to the legalese surrounding the tax code — filing a return is actually voluntary. (Courts would later bar Schiff from selling this book because of the false pretense that it would legally guide citizens through the murky waters of tax resistance. The full text can be found gratis online.)

A rather hectic and haphazardly compiled work (with some delightfully bad graphic design on the cover), The Federal Mafia makes as many questionable statements as it does seemingly legitimate ones. It should be noted that many have discredited Schiff as a crackpot whose interpretations of the tax code and subsequent refusal to surrender his tax liability landed him in prison on more than one occasion. Still, the dust jacket for The Federal Mafia features a blurb penned by former New York Times investigative journalist David C. Johnston, who applauds Schiff for his “confidence and seeming mastery of the tax law.” It is hard to deny Schiff’s skepticism surrounding the term “voluntary compliance” and the confusion that results from juxtaposing these seemingly contradictory ideas. In a moment of absurdist comic relief, Schiff purports to have phoned the IRS seeking a detailed explanation of the term:

I called and asked, “Is filing an income tax return based on voluntary compliance?” “It is,” I was told. “In that case,” I said, “I don’t want to volunteer.” “You have to volunteer,” I was informed. “If I have to volunteer,” I replied, “wouldn’t that make compliance compulsory and not voluntary?” “No,” the agent said, “voluntary compliance is similar to our motor vehicle laws; you voluntarily stop at a red light — but if you don’t, you get a ticket!” I object to this reasoning by pointing out that if I could get a ticket, stopping at a red light (or obeying other traffic regulations) was compulsory, not based on “voluntary compliance” at all. “No,” the agent insisted, “you stop voluntarily.”

The conversation shows a strong disagreement over notions of free will and the relationship between volitional independence and external influence. Schiff maintains a rather Thoreauvian position that being forced — by an outside actor such as the government, its agents, or the psychological threat of penalty — to make a decision under duress is a violation of personal autonomy. However, the federal government’s position (if we are to believe that the conversation with the above IRS agent is both representative and factual) is that wherever individuals have the power to decide whether or not to receive a penalty by performing specific, prescribed actions, they are freely making a choice. In this sense, we freely choose whether or not to follow tax laws, regardless of the fact that we do so under the shadow of penalty.

(On this point, Brunson noted that Schiff’s understanding of “voluntary compliance” was simply misguided on a definitional level: “‘voluntary compliance’ doesn’t mean that paying taxes is voluntary; it means we self-assess our taxes. While I can’t argue with the ridiculousness of Schiff’s approach, I have included him here to establish that even crazy, discredited madmen have offered more personal and political justification for not paying taxes than Donald Trump has.)

Julia Hill

Other tax protesters have objected to paying taxes on religious grounds or, as I do, because they don’t trust the government to use funds appropriately. Individuals in the American Quaker community have, on multiple occasions and across several centuries, withheld a fraction of their federal tax liability and requested that the government create a “conscientious objector” fund that would allow religious pacifists to pay their taxes without any of those taxes being redirected to military or combat efforts. Some of these cases are still tied up in the court system; still, if history is any indicator, the government has no problem waiting until the dissenting party can dissent no more at which point they will come a-knocking for money.

Photo by Gary Mattingly

On the political end of the spectrum, activist Julia “Butterfly” Hill, best known for her two-year stint living in a redwood tree in order to protect it from clear-cutters, participates in active tax redirection whereby she calculates the amount of tax liability owed and then informs the IRS that she donated this amount directly to causes she supports, such as after-school programs, arts and community programs, community gardens, and representative services for indigenous peoples. Hill, who studied business in college, does not believe she is a tax resister in the traditional sense; instead, she sees herself as an “investor” in America who is choosing to reapportion her tax liability so as to offer additional support to social services she feels have neglected:

…I actually take the money that the IRS says goes to them and I give it to the places where our taxes should be going. And in my letter to the IRS I said: “I’m not refusing to pay my taxes. I’m actually paying them but I’m paying them where they belong because you refuse to do so.” They are not directing our money where it should be going, they are being horrific stewards of that money.

Tough to argue with that, morally speaking anyhow.

Donald Trump will not be a good steward of your tax dollars, not this year, not next year, nor any other. Whereas tax resisters and tax protestors like Kellems, Schiff, the Quakers, and Hill all lodged objections against the income tax on legal, philosophical, or moral grounds, Trump has only offered cold and calculating vice as his excuse. “I’m very greedy,” he bragged on the campaign trail. “I’m a very greedy person.” This statement is perhaps the most verifiably accurate thing Trump has uttered to date.

So, you may be asking, what’s your new plan? To be honest, dear reader, I have no plan. I must concede that perhaps tax resistance is not the most effective retaliatory method for crippling our government or stopping Trump’s agenda. I’d envisioned thousands — maybe millions — of people simply not paying for unjustified wars, the brutalization of people of color, the legislative assault on women’s bodies, and cash grabs for corporations and wealthy individuals, among many other sins. At present, it just isn’t realistic or practicable.

I would remind you that our problems are far greater than one ruddy, feather-headed millionaire. As we strive to create a future and a government that works for us all, we must remind ourselves that when a man like Irwin Schiff — however nutty he may have been — is willing to go to prison for his political beliefs, there is a certain degree of integrity on display that we should not be quick to discount.

In contrast, when a man like Trump hires someone to eliminate his tax burden through loopholes, or when he registers his businesses in low-tax states like Delaware, or when he sets up offshore accounts to funnel and mask income, the only thing on display is the gross entitlement of the wealthy. Trump knows all too well that if you’re wealthy you can not only pay someone to dance around the IRS for you, you can also avoid being earmarked a criminal. Trump has benefited considerably from his material wealth, but also optically in that his affluence has allowed him to avoid being labeled a criminal despite documented incidences of domestic violence, sexual harassment, sexual assault, theft, and general deception. It’s all part of the same package deal.

So I concede defeat, but I have two silver linings to offer.

The first is that, if the Russian collusion stories turn out to have as much merit as many of us suspect they do, Trump will finally be exposed for his role in traitorously subverting American democracy. Of course, he would probably be pardoned by President Pence before a treason conviction could ever take place, but publicly witnessing the toppling of Trump’s crooked empire would be a glory to behold.

The second silver lining is a combination of theory and fantasy, and begins with the understanding that the gaze of history cannot be as easily duped as the rubes and closeted middle-class bigots that put Trump in office. True, this is little consolation for the real suffering taking place in our country at this very moment, but find whatever solace you can in imagining a day where the statue of Trump unveiled at Madame Tussauds Wax Museum earlier this year is moved out of the “American Presidents” exhibit and into the “American Gangsters” exhibit. Here, amidst the paragons of violence, racketeering, and greed, amid his peers and equals, Wax Donald Trump and Wax Al Capone will surely have a lot to talk about.

Eric Howerton is based in Stillwater, OK. He’s considering filing for an extension this year, allowing him to hold out until October 15.

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