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Donald Trump with his ex-wife, Ivana, and his father Fred in 1988. (Photo: Jeffrey Asher/Getty Images)

Trump Is Just One Player in a Much, Much Larger Tax Story

That big 'New York Times' expose should most of all remind us that upper-class tax evasion has been the norm for a generation

Matt Taibbi

 by Rolling Stone

When New York Times reporters David Barstow, Susanne Craig, and Russ Buettner published their exhaustive, gazillion-word expose on the Trump family tax practices last week, there was only one word for it.

“Tax bombshell,” blared Yahoo!

By my count, this was roughly the 4,790th “bombshell” of the Trump presidency, but one of the few to deserve the title. The Times story is an extraordinary piece of investigative reporting and a monument to the kind of work we all should be doing.

The parts I found most interesting were less about the rapaciousness of the Trump family per se than the myriad opportunities for gaming the system one presumes is available to everyone of this income level. The ordinary person cannot hire an outside appraiser to tell the IRS what it thinks he or she is worth, but the Trumps could systematically undervalue their properties for tax purposes (and then go back and overvalue them when it served their public relations needs).

The timidity that enforcement officials show toward the very wealthy is also a running theme in the story. When the Trump family claimed a $17.9 million building had fallen to $2.9 million, supposedly losing 83 percent of its value in just 18 days, the IRS auditor who caught it made them push the value back up by just $100,000.

The infamous $3.35 million casino chip scheme — an illegal multi-million-dollar loan under New Jersey law — inspired just a $65,000 fine.

There is a lot in the piece that testifies to Trump’s keen understanding of the media and how he knew he and his father could exploit it. Donald Trump, the bold filthy-rich investor, has always been a media creation. At an early age he realized reporters were basically dupes (and, usually, poorly paid dupes) who were easily conned into thinking a person was fantastically wealthy just by taking a ride past a few construction sites.

Donald and Daddy Fred furthermore understood that you can win an accomplice for life in the press just by telling a reporter something he or she thinks is a secret. In this piece, they’re shown pulling various insider-trading/greenmailing schemes, with Fred buying stakes in companies like Time, Inc. just before Donald would whisper to a reporter that he was “taking a sizable stake” in the company. Shares then jumped and Daddy cashed out with a $41K profit, which was probably enough for lunch, at least.

There is a lot in here that’s educational about how the wealthy are able to pass riches back and forth without being taxed the way you or I would be. The Times couldn’t find any paperwork explaining how Daddy Trump transferred 1,032 apartments to his children without incurring tax penalties. Tax records only showed that the “mini empire” had “shifted at some point from Fred Trump to his children.”

The expose is painstaking, incredible work. The late Wayne Barrett of the Village Voice — my old boss and one of Trump’s first biographers — kept a massive archive of Trump documents and spent years traversing this history. He would probably have shed a tear to see all this in print.

And yet, what will the impact be for Trump voters? I’m going to guess not much.

On the 2016 campaign trail, I couldn’t find anyone at Trump rallies who was bothered by the candidate’s multiple bankruptcies. That tale was also about a dynastic family manipulating the financial system to socialize losses and hoard assets. Trump’s excuse — that he had “brilliantly” manipulated the bankruptcy system to stay rich _ impressed most of the Trump voters with whom I spoke.

If they read the Times piece, Trump supporters are sure to seize on sentences like, “The line between legal tax avoidance and illegal tax evasion is often murky.” They will take that, add it to the fact that whatever Trump did, he clearly got away with it for a long time, and silently pump a fist: “Right on.”

What Trump sells to voters is a vicarious fantasy. He shows off his appalling gold-leaf interiors and shows his selfies with celebs and talks up his tacky empire, and people think: “Man, if I had a billion dollars, that’s how I’d live!”

Since most people don’t like paying taxes, Trump fans will probably applaud his family’s multi-generational avoidance. And they will look at stories like this and say, “Those reporters are only doing this because it’s Trump.”

They might have a bit of a point.

Where was this kind of hardcore investigative firepower into the brazen tax avoidance of the rich before?

There have been a few dedicated journalists like David Cay Johnston who, long before Trump, tried to evangelize for real tax collection from the super-wealthy. Johnston detailed horrific and brazen avoidance schemes and won critical acclaim, but not the same kind of attention.

I would describe Johnston’s explanation of how 61 percent of American corporations paid no taxes at all over a five-year period between 1996 and 2000 as a “bombshell,” but most of the journalism world did not agree.

Many of the biggest tax evaders are major media advertisers and sponsors of both parties — like Apple, for instance — which pioneered techniques like the “Double Irish with a Dutch Sandwich,” in which profits are sent overseas to tax havens.

Five years ago, the Senate Permanent Subcommittee on Investigations laid out in painful detail how Apple in one year paid an effective tax rate of five-hundredths of one-percent. There were similar gruesome tales about other tech companies.

The private equity business similarly has produced many politically active multi-millionaires and billionaires who have spread money across both parties. For this reason, some truly repulsive systemic tax-avoidance schemes have gone without requisite attention. It’s one of the reasons the absurd and indefensible carried-interest tax break (which helped people like Mitt Romney pay an effective 14 percent tax rate in 2011) was allowed to persist for so long.

Trump, of course, is likely far worse than the bulk of these actors. As the Times piece shows, his family’s whole business model was founded on a kind of scam. The key illusion involved a media-generated myth of self-generated opulence, when in fact what Trump mostly did is spend decades playing keep-away from the IRS with dollars inherited from Daddy.

But the time to sound the alarm about this was decades ago. Trump voters might have been more receptive to this kind of reporting back then, before we institutionalized corporate and high net-worth individual tax avoidance. In fact, the longstanding inattention of both parties and the commercial media to this kind of behavior perversely became part of Trump’s messaging in 2016.

This was what he meant by, “Nobody knows the system better than me. Which is why I alone can fix it.” People cheered that line.

I manipulated this corrupt nation to get rich at your expense wasn’t even the subtext there, but the primary meaning. America hates the IRS (although along with hemorrhoids and witches, they like it better than Congress) and Trump sold himself as an outlaw savior.

The Trump era has produced some stellar investigative reporting, but some of it yields an uneasy feeling. The relentless focus on Trump as the center of our media universe has left huge segments of the population with the impression he’s a cause, not a symptom, of our problems. He is a rich scumbag who cheats on taxes, not the rich scumbag who cheats on taxes.

If anything, the awesome amount of ink spilled about him as a symbol of upper-class impunity has furthered the deception described in this Times story as having begun in the Seventies, when he took reporters on tours of his quasi-fictitious “jobs.”

Trump is a person with a lot of money, but compared to tax-renouncing firms like Microsoft, Bank of America and Facebook — and even the executives running them — he’s a nobody, a putz. It’s great that we’re unmasking at least one person from that world. But please, let’s let it be just a start.

© 2021 Rolling Stone
Matt Taibbi

Matt Taibbi

Matt Taibbi is Rolling Stone’s chief political reporter. His predecessors include the likes of journalistic giants Hunter S. Thompson and P.J. O'Rourke. Taibbi's 2004 campaign journal "Spanking the Donkey" cemented his status as an incisive, irreverent, zero-bullshit reporter. His books include "Griftopia: A Story of Bankers, Politicians, and the Most Audacious Power Grab in American History" (2011), "The Great Derangement: A Terrifying True Story of War, Politics, and Religion" (2009), and "Smells Like Dead Elephants: Dispatches from a Rotting Empire" (2007).

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