Why Are Billionaires Tiptoeing Around Trump?

There’s an eerie silence in the C-suites of America. Where business leaders once proudly proclaimed their commitment to democracy after Donald Trump’s cardinal assault on it three years ago, they’re now loath to say anything about the state of the nation, even as it stares down the barrel of a democratic backslide. Save for the Elon Musks and Mark Cubans of the world—who have made full-throated and, in Musk’s case, full-bodied declarations of presidential allegiance—many of America’s most formidable chief executives think it’s in their best interest to sit this election out.

The New York Times reports that Bill Gates, who could financially swallow whole countries if they were for sale, is too afraid to publicly endorse Kamala Harris, despite privately funding her campaign with the understanding that “this election is different.” Jamie Dimon, the notoriously outspoken CEO of JPMorgan Chase, is reportedly telling friends and associates that he supports Harris but won’t say so aloud for fear of reprisal. (Dimon’s spokesperson has maintained that he has “never publicly endorsed a presidential candidate.”) Warren Buffet, who openly backed Barack Obama in 2008 and Hillary Clinton in 2016, has refused to throw his weight behind either candidate this cycle. Business leaders aren’t “condemning” Trump, Cuban recently told Rachel Maddow, “because they’re worried about his retribution or his vengeance.”

In the tech world, Meta CEO Mark Zuckerberg is also staying mum publicly, while privately telling Trump there’s “no way” he can support a Democrat. (That’s according to Trump, at least; a Meta spokesperson disputed the claim.) And on the media front, the

Los Angeles Times and The Washington Post, owned by billionaires Patrick Soon-Shiong and Jeff Bezos, respectively, each opted last week to not endorse Harris, an extraordinary, and ominous, break from editorial tradition that rattled staff and angered subscribers. Soon-Shiong took responsibility for the Times’ move, while Bezos has not directly commented. The Post, for one, reported that the decision was made by Bezos, while a Post spokesperson framed it as “a Washington Post decision.” (Vanity Fair has reached out to Bezos for comment.)

If you don’t particularly care about how billionaires signal political virtue, then their idleness might not concern you. But it should. Because chances are that every head of a Fortune 500 company is well-aware of the warnings that economists left, right, and center have been issuing for months now: That mass deportations, tariff hikes, and huge corporate tax cuts—to say nothing of the executive capture of the Federal Reserve—could immiserate America, tanking the dollar, spiking inflation, gutting employment, and sending national debt through the roof. “It is not hyperbolic at all,” as economist Kimberly Clausing told the Post, “to say this could cause a depression.”

Yet instead of guarding against this scenario by sounding the alarm, many corporate leaders have made the fiduciary equivalent of Pascal’s wager. They know that if Harris wins, the office of the presidency wouldn’t be weaponized against them—as has been the case under Joe Biden, who, despite his cri de coeur against shrinkflation and price gouging, has not been prone to singling corporations out. But when it comes to Trump, whose politics reside in personal grievance, business leaders have calculated that it’s safer to suffer the slings and arrows of neutrality if it means they might stay on the right side of his naughty-or-nice list. In polite terms, they’re engaging in what Timothy Snyder might call “anticipatory obedience.” In less academic argot, you might call it “cowardice.”

After all, these are the very same corporate leaders who paused funding to Trump and his allies after the Capitol riot; poured $50 billion dollars into racial justice initiatives during the George Floyd protests; and condemned the white supremacist Unite the Right rally after Trump said there were “very fine people on both sides,” leading to an exodus of CEOs from his business advisory councils in 2017. But, alas, railing against the seesawing scruples of corporate america has long been an empty exercise.

The more pressing matter is that public faces like Dimon, Bezos, and Gates—who have profited handily off of electoral democracy, such as it is—are failing to meet the moment in defending it. Like it or not, people of their stature are uniquely positioned to create a permission structure for mass dissent. And if they’re too risk-averse to do so today, before Trump’s potential presidency, then they should know that marshaling institutional resistance well into his term will be much, much harder. Consider, for instance, how long it took for our very own Gabriel Sherman’s Trump biopic to secure a limited release. Studios, producers, and streamers repeatedly blanched at the chance to be involved in The Apprentice, even though it was studded with bankable stars, signaling that Trump’s rhetoric has had a chilling effect on the entire industry. As he now threatens to strip broadcast licenses from the likes of CBS and ABC, who’s to say the same dynamic wouldn’t become widespread in media and entertainment under a second Trump term? He might only have to set just one or two examples; we need not imagine how.

If billionaires think they can somehow safeguard their finances from Trump’s political caprice, they’re mistaken. And I don’t say that simply a matter of MAGAnomics: Throughout Trump’s political rise, almost all of his lackeys—from Steve Bannon to Rudy Giuliani to Kevin McCarthy to Paul Manafort—fell out of his good graces as quickly as they weasled into them. Meanwhile, during his first term, Trump sparred with Bezos over the Post’s critical coverage and fanned the flames of COVID conspiracism around Gates, who aggressively criticized his administration’s response to the crisis. More recently, he demonized Dimon as an “overrated globalist” for supporting Nikki Haley during the GOP primary and threatened to imprison Zuckerberg for life under the notion that the Meta CEO swung the 2020 election in Biden’s favor. To think that Trump will suddenly defy his nature if he wins and let all of these bygones be bygones is a stunning leap of faith. And even if Trump did find forgiveness, there’s no telling what kinds of loyalty tests he’d subject those like Bezos, Dimon, and Gates to in the years to come. Take it from Trump himself, who said on social media in June: “Business Executives and Shareholder Representatives should be 100% behind Donald Trump! Anybody that’s not should be FIRED for incompetence!”

By sitting on the sidelines, billionaires are letting their empires careen into a chasm of uncertainty, because they find the promise of stability less assuring than they find tyranny terrifying. And it is terrifying. But the prospect of tyranny should be a galvanizing force for American industry—not an eventuality to hedge against.