Musk isn’t the first tycoon to flirt with a dictator. History hasn’t been kind.

Elon Musk just vaulted himself into some troubling historical company.

A bombshell report from The Wall Street Journal Friday morning revealed that Musk has secretly been in regular contact with Russian President Vladimir Putin for the past two years.

Musk might pitch himself to Americans as an avatar of the future, electrifying the car industry and leading humans to a sci-fi future on Mars. But the way he relates to geopolitics has unsettling echoes in America’s past, putting him in the company of business figures whose international misadventures have almost always been a black mark on their historical records.

At times the government has been able to rein them in. This time, it might not be possible.

Seasoned diplomats and government watchdogs were aghast at the report of Musk’s relationship with Putin, especially given Musk’s possible appointment to an ambiguous-but-sweeping role in a second Trump administration.

It’s unavoidable for international business leaders to have contact with foreign leaders, said Richard Stengel, an undersecretary of state for public diplomacy and public affairs under President Barack Obama.

This first appeared in Digital Future Daily, POLITICO’s afternoon newsletter about how tech and power are shaping our world. Subscribe here.

Musk’s relationship with a global pariah like Putin, however, carries another level of risk.

“This in particular is just much more sinister,” Stengel said. He called the report that Putin implored Musk not to activate Starlink service over Taiwan as a favor to Chinese President Xi Jinping “really dicey business.”

(Neither SpaceX nor X returned a request for comment on the report, or on Musk’s relationship with Putin.)

This might be norm-busting for a contemporary CEO, but Musk’s move has clear precedent in the behavior of tycoons of another generation, whose vast empires and outsize egos led them to write their own scripts on the global stage.

“Musk’s wealth is immense by historical standards, comparable to Carnegie and Rockefeller, so there aren’t too many points of comparison,” said Mark Wilson, professor of history at the University of North Carolina, Charlotte.

Musk’s use of his business empire to cultivate close ties with a brutal dictator actually is reminiscent of one Rockefeller — David, the head of what was then called the Chase Manhattan Corporation (and later of the Council on Foreign Relations) who in the 1970s tried to make nice with the deposed Shah of Iran and the perpetrators of the Chinese Cultural Revolution.

Then there’s Henry Ford, the paradigm-shifting carmaker with whom Musk is most often compared. Before Ford became the face of World War II-era isolationism, he embarked in 1915 on an ill-fated personal mission aboard his “Peace Ship” to stop World War I — an effort unsupported and unaligned with the administration of President Woodrow Wilson, who heard Ford’s pitch for the endeavor but declined to sponsor it.

“Every crackpot and nut in the country wanted to get on that boat,” a Brooklyn Eagle reporter noted at the time. Ford ultimately abandoned the trip out of fear for his company’s reputation, but he would remain active in anti-war politics, for a time heading up the isolationist America First Committee.

One pattern seems to be that moguls don’t mind sitting down with dictators if it prevents a conflict. Ford notoriously received emissaries and awards from Nazi Germany. William Randolph Hearst, in 1934, visited Hitler in Berlin, in a quixotic attempt to communicate American views of the Nazi regime to its leader.

According to the Journal’s reporting, Musk has been cultivating a direct personal relationship with one of the few world leaders on the Treasury Department’s blacklist, on which Putin sits aside North Korea’s Kim Jong Un and Syria’s Bashar al-Assad.

Whatever their ideological sympathies for history’s butchers, Ford, Hearst and Musk’s efforts all share a Pollyannaish belief that ruthless men with ambitious, complex geopolitical goals can be pacified if only they could just sit down and talk. It’s a worldview that only a man not used to hearing the word “no” might embrace, as when Ross Perot launched a batty mission to send the mercenary Bo Gritz into Southeast Asia to “rescue” POWs from the Vietnam War.

It’s also one of the primary critiques of Trump’s approach to foreign policy.

Sometimes there can be backlash. Perot didn’t canoodle with dictators, but his freelancing infuriated the Reagan administration all the same — and just a few months later, the Army canceled a massive contract with his Electronic Data Systems.

For Musk, it’s not clear that kind of repercussion is even possible. Plenty of information technology firms existed at the time to make up Perot’s contracts. But there’s only one company with the size and expertise to launch missions to the International Space Station, provide satellite internet access in crucial global war zones and break new ground by landing humanity’s first reusable rocket. And Musk controls it.

That means the American government is in a far trickier position than it was with any of these past moguls in putting a leash on his one-man diplomacy. (A Pentagon spokesman told The Wall Street Journal “We do not comment on any individual’s security clearance, review or status, or about personnel security policy matters in the context of reports about any individual’s actions.”)

“If this was any other contractor, it would be looked into by the agency … but the question about Musk is, is he ‘too big to fail?’” asked the former undersecretary of state Stengel.

In keeping with former President Donald Trump’s obsession with fin-de-siècle economics, Musk might be pushing America toward a new retro-futurism: the world of Ford and Hearst freely courting some of America’s worst enemies, with government helpless to rein them in and only their personal worldviews and consciences to dictate the terms of those relationships.