Trump's biggest vulnerability isn't his crimes — it's his humiliating failure
Using its agenda-setting powers for good instead of evil for once, the New York Times has released the second in a series of stories detailing exactly what kind of fraud Donald Trump is, using recently obtained copies of the tax returns the president has spent years desperately trying to hide.
This second one is a doozy, focusing as it does on how Trump, desperate for cash to prop up his failing empire, faked being a successful businessman on "The Apprentice." Then, because he is unbelievably bad at business, Trump managed to burn through the $424.7 million windfall he "earned" from that show, leaving him apparently dead broke before he announced his presidential campaign in 2015.
Much attention has been paid to the revelation from the first article in this series that Trump is a promiscuous tax cheat who uses all sorts of shady strategies — paying his daughter Ivanka as a "consultant" to hide money from the IRS, for one — to keep his income tax bill at zero in most years.
But this second article focuses on what is likely a far more potent slam against Trump in the eyes of the voters he'll need to win over if he wants to be re-elected in November: He is a comically terrible businessman. His real estate empire was kept on life support through ads with cartoon sheep and selling ringtones, as well multi-level marketing schemes and other ploys to defraud desperate people.
On Tuesday night we will see the first debate of the general election campaign. Right now, most liberal commentators are urging Trump's Democratic opponent, former Vice President Joe Biden, to talk about Trump's extensive tax cheating. That would actually be a mistake.
Instead, Biden should focus on how Trump's entire claim to be a captain of industry is a lie, and the fact that he's barely stayed afloat through laundry soap ads and tricking people into taking phony classes at "Trump University."
This may seem counterintuitive to liberals, who are offended by Trump's immorality and want to see him held to account for his corruption and criminality. But there's a real danger for Biden in harping on the fact that Trump is a bad person: Doing so runs the risk of making Trump look tough, smart and strong. Instead, Biden should characterize Trump as weak and stupid, which is far more likely to turn off the kinds of voters Trump needs to win in swing states.
Voters already know Trump is a lying scoundrel. If anything, that's a big part of his appeal, especially to those low-information and fair-weather voters who dragged him across the finish line in 2016. For many of those voters, Trump serves up a fantasy of the tough guy who breaks the rules to get things done.
Don't just take my word for it — the data backs this up. As Dan Pfeiffer, the former communications strategist for Barack Obama, explained in a recent newsletter, focus group and polling evidence shows that Trump actually benefits from telling "voters that norms and institutions are too weak to stop Trump from doing what he wants."
Trump's propagandists on Fox News and talk radio get this. Rather than denying that Trump is a tax cheat — something Trump himself has bragged about — they're hyping the cheating as evidence that Trump is smart and knows how to work the system.
Mollie Hemingway, conservative commentator and self-proclaimed Christian, defended tax cheating on Fox News Monday, declaring, "All of these things he's doing are things that probably all of us do."
Rush Limbaugh went even further, fawning over Trump's tax cheating as evidence that he's a "master" and an "expert."
By scolding Trump for being a naughty, Biden runs the risk of looking like the nagging police chief in an '80s cop drama, scolding our rogue-cop hero for bending the rules. Instead, Biden should try to kneecap Trump's efforts to look clever or strong by focusing on the fact that Trump was such an epic failure at business he needed to shill for laundry soap to keep his companies from collapsing entirely.
Trump is not a "master" or an "expert" or someone who knows how to "game the system." Trump, in reality, is this guy:
Among the joys of today’s NYT installment in the Trump Taxes saga is being reminded of the products Donald Trump wa… https://t.co/5LdrOVjtC7— Jim Roberts (@Jim Roberts) 1601381074.0
I attended the Republican National Convention in 2016, and one of the most interesting things was how much the programming avoided mentioning "The Apprentice." Instead, Trump was portrayed as this Ayn Rand-style titan of real estate, with lots of photos of cranes and men in hard hats.
Propping up this lie that he's a successful real estate mogul is central to maintaining the Trump mystique. The truth — that his real estate empire is a failure, which was barely kept alive by cash from reality TV, commercial endorsements and fraud — offers the only hope of dimming Trump's reputation, among a certain segment of voters, as a smart and successful businessman.
Focusing on Trump's failures as a businessman is not only a delicious way to humiliate him and degrade him in the eyes of his fans, it offers a path to connect Trump's failings to the real-life impact on voters.
It's difficult, if not impossible, to get voters to understand how Trump's cheating on his taxes affects them. Yes, tax cheating reduces government income that is needed for government services, but that's abstract accounting talk. Besides, no one is under the impression that Trump's tax bill was the make-or-break number for a federal budget that runs into the trillions every year.
But there's a way to explain why voters should care that Trump is such a failure at real estate that he was forced to hawk mattresses and marketing scams in order to stay above water. Over the last four years, Trump has run the government exactly like he ran his businesses, by failing miserably to do his job and covering up his failures with a bunch of lies and TV pageantry.
For instance, in the real world, Trump failed miserably to handle the coronavirus pandemic, despite being gifted with a massive public health infrastructure that was, at one time, the envy of much of the world. There are now 7.1 million Americans who have been infected and more than 205,000 who have died — which is more than 20% of the world's cases, in a country that has only 4.5% of the world's population.
But Trump doesn't care that he failed, because he believes he can fake success, "Apprentice"-style. Just last week, Trump declared on Fox News that he has done a "phenomenal job" and deserves an "A+" for his work on the pandemic.
Trump thinks he can fake his way through the presidency, just like he faked being a successful businessman. This is an easy, simple message. It's also likelier to resonate with undecided or shaky voters than the message that he's a nefarious tax cheat, which runs the risk of making him sound more competent than he actually is.
Trump desperately wants voters to believe he's a master builder and real estate king. Biden would do well to remind them how Trump actually made the money he then proceeded to lose: By shilling for multi-level marketing schemes and cut-rate pizza chains.