You are using an outdated browser.
Please upgrade your browser
and improve your visit to our site.

The Worst Businessman in America

The revelations about Trump's taxes prove he was a grifter and a fraud, a braggart and a blowhard. In other words, he was the same man he is today.

TIMOTHY A. CLARY/AFP/Getty Images

Any dwindling belief that Donald Trump’s business career represented anything other than “The Art of the Scam” died Tuesday night when The New York Times reconstructed the president’s federal tax returns from 1985-1994. In a feat of forensic work worthy of a TV crime series, reporters Russ Buettner and Susanne Craig revealed that Trump lost $1.17 billion in a decade and “appears to have lost more money than any other individual American taxpayer.”

Trump’s dazzling failure helps explain how he and the Republicans have given the nation an era of nearly $1 trillion in annual deficits, despite the buoyant economy.

The Times’ scoop is bracing, even if it comes too late to convince Trump loyalists that they have been hoodwinked by a fraud (if they ever were convincible). What it does suggest is that no coverup lasts forever—and that, sooner or later, Trump’s more recent tax returns will be made public.

Treasury Secretary Steven Mnuchin has been stonewalling the House Ways and Means Committee’s demand, buttressed by a 1924 law, for the last six years of Trump’s federal returns. In a coincidence that might embarrass a political novelist, the Times’ story broke just as Mnuchin was attending a 2020 Trump fundraiser—the kind of event past treasure secretaries have avoided out of conflict-of-interest concerns.

But just as New York’s tabloid culture of the 1980s and 1990s made Trump, his residency in the state may ultimately break him. The New York legislature, which has its own hefty share of grifters, is moving toward approving a bill that would provide Trump’s state tax returns to the House Ways and Means Committee on request.

Since the information on state and federal taxes is virtually identical, such legislation might help solve the tantalizing mystery of why and how Trump, who worshipped debt, began paying for expensive properties (including golf courses) with cash in 2006. It is worth noting that the Mueller report neither went back that far nor scrutinized Trump’s finances.

The Times bombshell story also revealed that in business—if, alas, not yet in politics—Trump the Braggart eventually became exposed as Trump the Blowhard.

One of Trump’s few profit-making ventures in the late 1980s was his version of the age-old Wall Street boiler-room scam known as “pump and dump.” Repeatedly, Trump would announce that he was seeking to acquire majority control of a major company like United Airlines and then, when the stock jumped, he’d sell his relatively small holdings at a major profit. Trump pulled off the same scheme with publicly touted investments in Hilton Hotels, Gillette, and Federated Department Stores.

But stock analysts, with money on the line, noticed that Trump never followed through after his initial braggadocio about a takeover attempt. In late 1989, a purported Trumpian raid on American Airlines inspired mostly yawns and giggles. According to the Times’ analysis, Trump appeared to have lost more than $30 million when American Airlines stock dropped sharply.

Thus ended the ignominious saga of Donald Trump, Corporate Raider.


The more detail we learn about how little Trump appears to have learned about business during his undergraduate years at the Wharton School, the more it becomes apparent that the president owes most of his patina of success to Jeff Zucker.

As the head of NBC’s entertainment division in 2004, Zucker put the all-hat-and-no-cattle New York real estate hustler on the air as the host of The Apprentice. Then in 2015 and 2016, CNN, now headed by Zucker, promoted Trump’s presidential candidacy even more egregiously than Fox News.

Trump implicitly acknowledged the accuracy of the Times’ tax reporting when he tweeted early Wednesday morning, “You always wanted to show losses for tax purposes ... it was sport. Additionally, the very old information is a highly inaccurate Fake News hit job!” In his tweets, Trump claimed that his red-ink bookkeeping was all real estate gamesmanship, even though the Times’ story pointedly declared, “Depreciation cannot account for the hundreds of millions of dollars in losses Mr. Trump declared on his taxes.”

In theory, the revelation that Trump was the biggest loser during his supposed heyday in New York real estate should embarrass some 2016 Republican voters about their gullibility. During the 1980s, Hillary Clinton, at least, made a dubious $100,000 in profits in commodities futures.

The truth is that when a president seeks reelection, the only things that matter to the voters are what he did in the Oval Office—and not his record prior to the White House.

Ronald Reagan’s prior career as a B-list actor was a Democratic talking point in 1980, but it had scant political relevance when the Gipper won a 49-state landslide in 1984. Republicans failed to make Bill Clinton’s tangled investment in the Whitewater real estate development in Arkansas a 1996 campaign issue. And with the Iraq War raging in 2004, George W. Bush’s Vietnam-era billet in the Alabama Air National Guard came across as a penny-ante scandal.

Similarly, the case against Trump’s reelection should be built around his bilious, maladroit, lawless presidency rather than his long-ago billion-dollar business failures. In fact, judging from 10 years of Trump’s taxes, he may be even more inept at making money than he is at governing the nation.


The Times’ story ended with this satisfying knife twist: “While Donald Trump reported hundreds of millions of dollars in losses for 1990 and 1991, Fred Trump’s returns showed a positive income of $53.9 million, with only one major loss: $15 million invested in his son’s latest apartment project.”

In a just world, Trump would be brooding in Trump Tower about his life of upward failure and his inability to ever please his late father, Fred. Instead, he is brooding in the White House about the battle over his tax returns, the fight over the unredacted Mueller report (which Trump is now trying to withhold through executive privilege), and the fight over the cavalcade of administration witnesses subpoenaed by the House. He must sense that the water is rising around him. He is the White House version of Mickey Mouse as the Sorcerer’s Apprentice, desperately flailing as the bucket brigade keeps coming at him.

Probably, in his twilight hours, Trump wishes that he still had Roy Cohn at his side, embellishing his lies and giving a Bronx cheer to the concept of justice. Of course, in a hint at Trump’s rendezvous with history, Cohn was disbarred on his deathbed for “dishonesty, fraud, deceit and misrepresentation.”