Jeff Bezos, Elon Musk and the Billions of Ways to Influence an Election

The world’s richest men have their own rocket fleets, their own media and their own schemes to succeed with Donald J. Trump.

Entrepreneurs become legends when they make big bets on technology that pay off in a huge and dramatic way. Elon Musk is now applying that all-or-nothing philosophy to a presidential election, tying his reputation and perhaps his future to a win by Donald J. Trump.

Jeff Bezos, the reigning swashbuckler of the internet age until Mr. Musk came along, was playing a cooler game, content to let Mr. Musk take the headlines and the risk. Then last week Mr. Bezos ventured — well, stumbled — into the heart of the news.

Among his many properties is The Washington Post, which he bought in 2013. The paper’s editorial board was preparing to recommend the Democratic nominee for president, Kamala Harris, when Mr. Bezos canceled the endorsement at the last minute.

It wasn’t supposed to be a big deal, just a ho-hum announcement of something not happening. Instead the greatest salesperson of the era, whose customer obsession had made Amazon into a colossus of modern retail, got the greatest customer rejection of a lifetime.

A quarter-million Post readers canceled their subscriptions, a figure first reported by NPR and then by The Post itself. That is about 10 percent of the total circulation. The speed and decisive force of the cancellations was a bit of a shock but also weirdly appropriate, said Danny Caine, author of “How to Resist Amazon and Why.”

“Amazon invented the whole notion of one-click culture, where you click a button and there’s a bunch of toilet paper on your porch,” he said. “You can’t get rid of a Tesla in your driveway with one click. But you can with the newspaper that Jeff Bezos owns.”

Those canceling said they felt Mr. Bezos was trying to curry favor with Mr. Trump, a charge he denied. The furor immediately exceeded any damage incurred by Mr. Musk since he endorsed Mr. Trump in July and became the former president’s most visible fan, cheerleader and acolyte.

If customers are rejecting the electric vehicles made by Mr. Musk’s car company, Tesla, for political reasons, it hasn’t clearly shown up in the sales numbers. Mr. Musk implicitly dismissed the notion on X on Tuesday, reposting an admirer’s note that said it wasn’t happening.

Mr. Musk, Mr. Bezos and other extremely rich people are confronted with unusual opportunities and invisible perils in the tightest, most dramatic, chaotic and highest stakes political battle in modern times. Everyone has a stake in this election, of course, but the very wealthy have so much at stake — or at least think they do — that they are perhaps inevitably trying to shape it, too.

There has always been money in politics, and rich people who sought their reward in Washington. President Dwight D. Eisenhower’s first cabinet was known as “eight millionaires and a plumber.” But until recently, it was literally considered bad business for successful public figures to declare favorites too stridently and make too many demands.

Michael Jordan established the standard for many celebrities in 1990. The basketball superstar, who went to college in North Carolina, was asked about whether he would endorse Harvey Gantt, the Black candidate running to dethrone Jesse Helms, the Republican senator with a long opposition to civil rights.

“Republicans buy sneakers, too,” Mr. Jordan said. Mr. Helms narrowly beat Mr. Gantt.

Mr. Jordan later said it was an off-the cuff remark, a joke even, but he did not really back away from it. “I never thought of myself as an activist,” he said. “I thought of myself as a basketball player.”

Many billionaires now are activists. One reason is there are more of them — the ranks of U.S. billionaires are up 38 percent by one estimate since Mr. Trump first took office in 2016 — and they have even more money. For all the specter of antitrust and regulation, life has been very good for the rich and their companies. The stock market is perpetually at a record high.

Even this ocean of money has a limit, however. Larry Ellison, the founder of Oracle who ranks just behind Mr. Musk and Mr. Bezos as one of the richest men in the world, last year backed the presidential aspirations of Senator Tim Scott, a South Carolina Republican. Mr. Ellison spent at least $30 million but could not make Mr. Scott a viable candidate.

Mr. Ellison came up with the funding for his candidate but was otherwise quiet. Mr. Musk is anything but reticent and has become a full-scale surrogate for Mr. Trump, as well as one of his biggest donors. Speaking at the Trump rally at Madison Square Garden on Sunday, Mr. Musk told the crowd, “We’re going to get the government off your back and out of your pocketbook.”

Mr. Musk would no doubt like to get the government off his own back. His companies, including Tesla and SpaceX, are the subject of over 20 investigations or reviews, a New York Times examination found. Tesla’s push for autonomous driving is a particular focus for regulators. Just last week, the National Highway Traffic Safety Administration said it was investigating several self-driving crashes involving fog and dust.

Mr. Musk, who has offered himself to Mr. Trump as a sort of inspector general for government waste, has regularly tussled with the Securities and Exchange Commission. The commission has probed the entrepreneur’s 2022 purchase of X, then called Twitter. Mr. Musk did not show up for a deposition in September, leading to an S.E.C. request that sanctions be imposed on him.

Beyond the regulatory scrutiny, Mr. Musk is tied to the government through funding. NASA announced in June that SpaceX got an $843 million contract to “de-orbit” the space station when it is ready for retirement in a few years. SpaceX has contracts to launch military and spy satellites. It also received contracts in 2021 and 2022 worth a total of $4 billion to take humans to the moon twice. It is working on many other projects involving the government.

Mr. Bezos, too, has business with the government. Most notably, the U.S. Department of Justice is bringing Amazon to court, accusing it of antitrust violations.

When Mr. Trump was president, Amazon and its chief executive were sometimes the subject of his barbs. The company bid on a $10 billion cloud computing contract that the Pentagon awarded Microsoft. Amazon sued, saying Mr. Trump had undermined its bid. The contract was canceled. Ultimately four tech companies, including Amazon and Microsoft, got a part of the cloud deal.

The most vulnerable Bezos property in a new and vindictive Trump administration is probably the one he cares about most: his space company, Blue Origin. The company will compete with SpaceX and a third firm to provide launch services for national security rockets over the next five years.

On Friday, when The Post announced it would not endorse a presidential candidate, Blue Origin’s chief executive, Dave Limp, had a brief meeting with Mr. Trump in Texas. Mr. Bezos did not respond to a request for comment but said in a piece he wrote in The Post on Monday that he knew this “would provide ammunition to those who would like to frame this as anything other than a principled decision” and that the whole thing was a coincidence. That article drew over 24,000 comments, few of them favorable to Mr. Bezos.

A few hours later, Mr. Musk posted on X: “Kudos to @JeffBezos.” It’s possible he was tweaking Mr. Bezos, like the time an interviewer asked about him and Mr. Musk responded “Jeff who?” Mr. Musk did not respond to a message for comment.

For Gordon L. Johnson II, a New York securities analyst and die-hard Tesla skeptic, everyone is acting rationally: “They’re trying to save their tails.”

The best-case scenario for Mr. Musk if Mr. Trump wins, he said, “is that Trump says, ‘Forget about the open cases the D.O.J. and S.E.C. have against you,’ ” he said. “The risk if Kamala wins is that the current investigations continue.”

As for Mr. Bezos, he is also doing the sensible thing, Mr. Johnson said.

“If you want to protect your business interests, cowardice is a rational thing,” he said. “We’ve never had a president threatening the things Trump has threatened.”

Mr. Johnson knows he, too, must behave rationally.

“I have a ‘sell’ rating on Tesla,” he said. “If Trump wins and Musk is in government, who knows what is going to happen to his enemies. I have a 4-month-old son and Daddy going to jail would be a problem. I’m not rich. I’d drop my coverage of Tesla.”

Which would be another win for Mr. Musk.