White House senior adviser Jared Kushner, second from left, joins President Trump and others for a meeting with Vietnamese Prime Minister Nguyen Xuan Phuc at the White House. (Jonathan Ernst/Reuters)

Evan Thomas is the author of “Robert Kennedy: His Life.”

Jared Kushner is not the first member of a presidential family to try to open a back channel with the Kremlin. John F. Kennedy’s brother Robert met secretly with a Soviet intelligence agent named Georgi Bolshakov many times during the Kennedy administration. Their dealings illustrate the shortcomings and dangers of informal high-level diplomacy — but also the potential for breakthrough in a crisis.

The Kennedy brothers were, in their way, as highhanded as the Trump family. President Kennedy appointed his own brother to be attorney general — the nation’s chief law enforcement officer. (Their father, Joseph Kennedy, insisted.) Among the personal scandals Bobby had to cover up were the president’s extramarital relations with Judith Exner, the girlfriend of Chicago mafia don Momo Giancana, and with call girl Ellen Rometsch, suspected by the FBI of working as an East German spy. (As I recounted in my biography of RFK, Rometsch denied both the spying and the sex, but RFK had her deported nonetheless.) More substantively, JFK used RFK to run covert actions against Cuba, including assassination plots against Fidel Castro.

So perhaps it is unsurprising that, in late April 1961, during the first year of the Kennedy administration, when Soviet spy Bolshakov, using an American newspaperman as an intermediary, first approached Attorney General Kennedy for a secret meeting, Bobby did not hesitate to say yes. Bolshakov posed as the editor of a glossy English-language publication on Soviet life. Under cover, he was a colonel in the GRU, the military counterpart of the KGB. More significantly, his patron in Moscow was Aleksei Adzhubei, son-in-law of Soviet leader Nikita Khrushchev.

(Thomas Johnson/The Washington Post)

On the afternoon of May 9, the U.S. attorney general and the Soviet spy sat together on a park bench on Constitution Avenue, near the Justice Department. “Look here, Georgi, I know pretty well about your standing and your connections with the boys in Khrushchev’s entourage,” Bolshakov later recalled RFK saying, according to Richard Reeves’s biography “President Kennedy: Profile in Power.” “I think they wouldn’t mind getting truthful firsthand information from you, and I presume they’ll find a way of passing it on to Khrushchev.”

The president’s brother and the short, tubby Russian spy met dozens of times over the next 18 months. The Kennedys had been warned against relying on the bureaucrats at the State Department by their father, who felt he had been undone by professional diplomats during his rocky tenure as ambassador to Britain at the beginning of World War II. JFK viewed State as slow-moving and lightweight. “They’re not queer, but, well, they’re sort of like Adlai,” he said, referring to Adlai Stevenson, the U.S. ambassador to the United Nations.

Bobby was not particularly articulate, and the Russians sometimes did not understand him. The president’s brother was also remarkably indiscreet. He told the GRU agent that the U.S. Joint Chiefs of Staff had “offered the president a report in which they confirmed that the United States is currently ahead of the Soviet Union in military power and that in extremis it would be possible to probe the forces of the Soviet Union.” Kennedy’s loose use of the word “probe” set off alarm bells in the Kremlin. Did he mean the Pentagon was contemplating a preemptive strike?

For his part, Bolshakov sometimes lied to RFK. On Oct. 5, 1962, the GRU agent reassured Kennedy of Khrushchev’s promise that Soviets would put only defensive weapons in Cuba. Less than two weeks later, American U-2 spy planes flying over Cuba photographed nuclear-tipped missiles that could reach Washington. The most dangerous crisis of the Cold War had begun.

But it was also the Bolshakov back channel that first hinted the way out. On Oct. 23, the morning after the president announced a blockade of Cuba and millions of Americans faced the real prospect of nuclear war, RFK passed a message to Bolshakov. In 1993, historians Timothy Naftali and Aleksandr Fursenko found Bolshakov’s cable in the papers of the Soviet foreign office in Moscow: “R. Kennedy and his circle consider it possible to discuss the following trade: the U.S. would liquidate its missile bases in Turkey and Italy, and the USSR would do the same in Cuba.”

That is exactly the deal that was struck by Robert Kennedy, meeting privately and secretly with Soviet Ambassador Anatoly Dobrynin on the night of Oct. 27. Over the intervening four days, the saga of the Cuban missile crisis had taken numerous twists and turns — and come perilously close to the brink — but the Kennedys’ penchant for back channels, in the end, had proved useful, and possibly essential.

Back channels can be a terrible idea. They can sow confusion by subverting normal diplomacy and, potentially, precipitate disaster by expressing the unchecked will and wiles of headstrong leaders. But they can also lead to peace. President Richard Nixon’s opening to China in 1973 was run entirely through a back channel opened by his national security adviser, Henry Kissinger — who was also running a back channel to the Kremlin. It would be interesting to know to what extent Kissinger is advising Kushner.