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

At times the government has been able to rein them in. 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.” 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. 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. 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.