Kremlev’s previously unreported relationship with Trump Jr. represents an extraordinary development: a member of Putin’s circle financially supporting the president’s son and gaining intimate access to the Trump family. For a decade, Putin’s government, regarded as a chief adversary of the U.S., has been accused of efforts to influence American elections. Attempts by Russia to make inroads with the Trumps before the 2016 election exploded into controversy that dogged much of the president’s first term. Do You Have Information We Should Know About Donald Trump Jr.?

National security experts expressed alarm at Trump Jr. accepting the oligarch’s largesse, saying it raised an urgent question: What motivated Kremlev to spend a fortune cultivating the connection?

“If I’m paying for your wedding, at some point, you’re going to owe me something,” said Frank Montoya Jr., a retired career FBI official who held senior counterintelligence roles. Oligarchs like Kremlev often act in coordination with the Russian government. While it’s unclear if that happened here, Trump Jr. put himself in a precarious position, Montoya said. “This should be unthinkable for the son of the president. End of story.”