SAN FRANCISCO >> 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 Trump.

Jeff Bezos, the swashbuckler of the internet age until Musk came along, was playing a cooler game, content to let Musk take the headlines and the risk. Then, last week, Bezos made news.

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

It wasn’t supposed to be a big deal, but a quarter-million Post readers canceled their subscriptions, a figure reported by NPR and the Post. That is about 10% of the total circulation.

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

Many billionaires now are activists. One reason is there are more of them — the ranks of U.S. billionaires are up 38% by one estimate since 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 Musk and Bezos as one of the richest men in the world, last year backed the presidential aspirations of Sen. Tim Scott, R-S.C. Ellison spent at least $30 million but could not make Scott a viable candidate.

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

Musk would no doubt like to get the government off his own back. His companies, including Tesla and SpaceX, are the subject of more than 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.

Musk, who has offered himself to 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. Musk did not show up for a deposition in September, leading to an SEC request that sanctions be imposed on him.

Beyond the regulatory scrutiny, 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.

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 Trump was president, Amazon and its CEO were sometimes the subject of his barbs. The company bid on a $10 billion cloud computing contract that the Pentagon awarded to Microsoft. Amazon sued, saying 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.