Democrats Should Troll Donald Trump Over His $1 Billion in Business Losses From Now Until Eternity

Donald Trump waves outside of the White House.
Trump arrives for an event to celebrate the first anniversary of the “Be Best” initiative in the Rose Garden of the White House on Tuesday. Brendan Smialowski/Getty Images

Somebody seems to have slipped the New York Times a decade’s worth of Donald Trump’s tax information, and as a result, we now know that our president claimed losses from his businesses every single year between 1985 and 1994, totaling more than $1 billion.

If it turns out that those losses were real, it would be devastating for Trump’s personal mythology. The story suggests his image as a successful business mogul was a mirage virtually from the start—that his empire was in deep trouble well before the early ’90s real estate bust or his casino bankruptcies nearly brought him to the brink of a public downfall. “He’s got to be, quite literally, the most successful con artist of all time, right?” MSNBC’s Chris Hayes wondered after the story published. “Who comes close?”

The president, however, claims that his only illusion was the red ink. On Twitter on Wednesday, Trump explained that the losses were just the result of tax games, which he called a “sport.”

Whichever story is closer to the truth, the Times’ revelations should be politically damaging for Trump, and any Democrat who runs against him in 2020 ought to throw it in his face whenever they’re on a debate stage together.

To people who follow politics, the idea that Donald Trump is a self-promoting fraud who was born into a wealthy real estate family and ran various businesses into the ground before reinventing himself as a branding guru and reality TV star is basically old hat. This is part of the reason that the Timesbig scoop last October showing that Trump received some $413 million over the years from his real estate developer father was greeted with a bit of a shrug in media circles, even though it made a mockery of Trump’s old line about how he started in business with no more than a $1 million loan from his dad.

As Matt Yglesias notes, however, many Americans do not actually know the president’s life story. Instead, they believe Trump was the self-made entrepreneur he played on TV—and that shapes their opinion about him. In a series of surveys between 2016 and 2018, researchers from the University of Maryland found that a large chunk of Americans appeared to have no idea Trump was born rich. As of last year, barely more than half seemed to realize it.

People don't realize Trump is rich
McDonald, Carol, and Mason, 2019

This confusion has almost certainly helped Trump’s public image. In a randomized experiment, the Maryland researchers found that telling survey takers Trump was born wealthy and that his father had to bail out his companies made them less likely to say the president understood the struggles of average Americans or that he was good at business. Giving voters more information about Trump’s biography even seemed to hurt his standing among Republicans.

Democrats often make the mistake of assuming that everybody knows and understands the same basic facts about politics. They do not. And swing voters are often especially low on information. Many of them would probably be surprised to learn that Trump inherited a fortune from his pops, and that at the time Trump was becoming famous for The Art of the Deal, his taxes suggest he was losing money year after year. This knowledge might even make such voters feel a bit less inclined to cast a ballot for him. Sure, the next election will probably be a referendum on Trump’s actual term in office. But it can’t hurt to tell voters that the guy has always been running a con.

Trump’s defense of his business record isn’t exactly a political winner either. The president claims that his business losses largely existed on paper, thanks to the generous deductions and write-offs that the real estate industry was entitled to in the 1980s. This might even be true. To this day, for instance, developers and property owners are allowed to claim losses from depreciation on their buildings, even if they’re actually increasing in value. The Times argues that depreciation alone can’t explain Trump’s red ink. But some experts believe that Trump might have benefited from a bizarre loophole called debt parking that for many years let developers write off their lenders’ losses on projects on their own taxes. (Congress closed that loophole in 2002.) “The president got massive depreciation and tax shelter because of large-scale construction and subsidized developments,” the White House told the Times in a statement. “That is why the president has always scoffed at the tax system and said you need to change the tax laws. You can make a large income and not have to pay large amount of taxes.”

The problem, as New York magazine’s Eric Levitz points out, is that Trump already passed a massive tax bill that left the real estate industry’s treasured write-offs unscathed, while creating a few new giveaways to developers and investors. If Trump wants to claim that the IRS code is actually the problem, Democrats have an easy response: Why didn’t you try to fix it?

As a political tactic, trolling Trump over his business record accomplishes one of two things: It either reminds voters—who already doubt his honesty—that the president is a lifelong fabulist. Or it forces him to talk about why he passed a tax cut that curbed tax deductions for homeowners, but not property developers like him. It’s a win-win.