Any CEO with a memory of Trump’s first term knows that it’s wise to take those threats seriously, as the president didn’t hesitate to sound off and, with a single tweet, sink a company’s stock or spark a boycott.

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If reelected, Donald Trump has made clear that he plans to exact revenge on the people and institutions he perceives as a threat. His “enemies” list seems to be constantly growing as the election nears, and includes Democratic politicians, the media, lawyers and political donors who he believes were “involved in unscrupulous behavior.”

Any CEO with a memory of Trump’s first term knows that it’s wise to take those threats seriously, as the president didn’t hesitate to sound off and, with a single tweet, sink a company’s stock or spark a boycott.

While dozens of American business leaders — your Reid Hoffmans, your Mark Cubans, etc. — have used their money and power to resist that kind of bullying and endorse Vice President Kamala Harris, others are choosing to bend the knee. Or to keep just quiet enough to avoid being becoming a target.

Jeff Bezos, owner of The Washington Post, didn’t endorse Trump explicitly. Instead, he blocked the paper’s editorial page from endorsing any candidate for the first time in decades — a not-at-all subtle nod to the Republican nominee, and one that legendary former Post editor Marty Baron called an act of cowardice. That move came shortly after the billionaire owner of the Los Angeles Times, Patrick Soon-Shiong, vetoed his editorial board’s endorsement of Harris.

Baron, who retired from the Post in 2021, on Saturday told CNN’s Michael Smerconish that Trump has threatened Bezos “continually,” but that Bezos had previously resisted that pressure.

“I was very grateful … for his willingness to stand up to the pressure from Donald Trump in 2015 … until now. But the fact is that Bezos has other commercial interests,” including a large stake in Amazon and a private space company, Blue Origin.

And Blue Origin, of course, competes directly with SpaceX, the rocket maker owned by outspoken Trump supporter Elon Musk, for government contracts.

“Trump rewards his friends and he punishes his perceived political enemies, and I think there’s no other explanation for what’s happening right now,” Baron said.

To be clear: What Bezos and Soon-Shiong did here, under a guise of neutrality, is take a very loud position. No Washington Post or LA Times editorial, with all due respect to those institutions, was ever going to meaningfully sway the electorate. But pulling them creates news, and it’s news for an audience of one.

(And for Bezos, at least, it may also turn out to be a shockingly bad business decision. As NPR’s David Folkenflik reported Monday, some 200,000 people had canceled their digital subscriptions to the paper — about 8% of its subscriber base — over the decision.)

Late Monday, Bezos defended the move in an op-ed, writing that there was “no quid pro quo of any kind” behind his decision and claimed that the timing, less than two weeks before Election Day, was due to “inadequate planning, and not some intentional strategy.”

Other rich executives are doing diplomacy behind the scenes, as my colleagues Steve Contorno and Alayna Treene reported:

  • Apple CEO Tim Cook recently chatted with Trump about the company’s legal issues in the European Union, the former president said last week. (Apple didn’t respond to CNN’s earlier request for comment.)
  • Trump told a Las Vegas audience that the “head of Google,” (presumably CEO Sundar Pichai) called to marvel over the Republican nominee’s campaign stop slinging french fries at a Pennsylvania McDonald’s. (A Google spokesperson said the company had “nothing to share” on Trump’s claim.)
  • Amazon CEO Andy Jassy also recently reached out to check in with the former president, two people familiar with their phone call told CNN.
  • And Mark Zuckerberg, the CEO of Meta whom Trump has threatened to send to prison for life, called the former president to wish him a speedy recovery after the first failed assassination attempt against him, a person familiar with the conversation said.

Executives have plenty to worry about under a Trump 2.0 White House, particularly when it comes to trade policies that would force American companies to pay exorbitant markups to the US government for supplies imported from overseas. On top of that, Trump has promised to deport millions of undocumented immigrants, potentially creating a labor shortage, and to put himself in a position to influence interest-rate policy.

That’s why 88 business leaders last month endorsed Harris.

But in a race this close, many executives are hedging their bets. Sticking their necks out to express their concerns doesn’t really benefit anyone if Trump wins and decides to do, like, all the things he has repeatedly promised to do. On the other hand, a little back-channeling and olive-branch-extending could give business leaders and their companies some goodwill in an administration helmed by a notoriously impulsive, vengeful leader.

In a business world that craves certainty and economic stability, executives may be telling themselves that their silence is purely a business decision. But staying quiet is a choice, and it’s not a neutral one when you’re a billionaire with real power.