In recent days, as Donald Trump Jr. has found himself in hot water over a newly disclosed meeting that he took with a Kremlin-connected Russian lawyer during his father’s presidential campaign last year, some historically minded observers noted that this is not the first time Russian operatives have sought to engage with a campaign for the U.S. Presidency.

In June 2016, Russian lawyer Natalia Veselnitskaya reportedly promised to provide the younger Trump with damaging information about Hillary Clinton’s campaign. Trump said Sunday that “claims of potentially helpful information” ended up being a “pretext” for a meeting that ultimately focused on a program that previously allowed Americans to adopt Russian children. News of the meeting — which is the earliest known private meeting between Trump aides and a Russian — comes amid investigations into possible collusion between Russia and the Trump campaign.

Nearly six decades earlier, Soviet leader Nikita Khrushchev supported John F. Kennedy over incumbent Republican Vice President Richard Nixon in the 1960 Presidential election. Nixon, as serving VP, represented a past during which Khrushchev had struggled to connect to his Cold War counterparts. Khrushchev had also clashed with Nixon during a July 1959 debate in Moscow over the benefits of socialism versus capitalism. Khrushchev was offended and came to believe that “any candidate would be better than Nixon,” Vladislav Zubok and Constantine Pleshakov write in the book Inside the Kremlin’s Cold War: From Stalin to Khrushchev.

And, thanks in part to the public writings of a former Soviet intelligence officer, which the authors cite, it is believed that Russian operatives even attempted to contact Kennedy campaign officials during the 1960 election, only to be denied.

“Never before had Khrushchev followed a U.S. presidential campaign so closely,” Zubok and Pleshakov write. And, accordingly, Khrushchev sought to influence the outcome to his liking:

Alexander Feklisov, then the KGB station chief in Washington under the alias ‘Fomin,’ recalls that ‘the rezidentura [station] had been instructed to inform the Center periodically about the development of the electoral campaign, and to propose measures, diplomatic, propagandist, or [any] other, to encourage Kennedy’s victory.’ A KGB agent, according to Feklisov, even tried to contact Robert Kennedy, but met a polite rebuff.

As the New York Times pointed out when Feklisov died in 2007, the nature of Feklisov’s career and the difficulty of checking anything having to do with the KGB has meant that it is hard, if not impossible, to independently confirm Feklisov’s story. He would have been, however, in a position to know of such an overture being made. And Khrushchev’s feelings about the election were no secret.

In fact, he later claimed credit for Kennedy’s victory, even without having actively cooperated with the campaign: the Soviets held captive two American pilots, Captains Freeman Olmstead and John McKone, whose plane was shot down over the Soviet North in July 1960, despite efforts by Nixon to negotiate their release before Election Day.

The Soviets knew that the failed negotiations reflected poorly on Nixon, as Zubok and Pleshakov write:

When Kennedy won the presidential election on November 4, Khrushchev was delighted, and even joked that this was a present to him on the anniversary of the great October Socialist Revolution. Later, when Khrushchev met Kennedy in Vienna, he did not hesitate to boast that he had helped the Democrat win an extremely narrow race with Nixon.

Olmstead and McKone were released in 1961, shortly after Kennedy’s inauguration, and the new President was able to announce their release at his first news conference. TIME reported on their return to the U.S. with a cover story on Feb. 3, 1961, headlined “Return of the Airmen”:

In human terms, the release of Bruce Olmstead, 25, and John McKone, 28, was a heart-touching event. In diplomatic terms it was a blatant Khrushchev move in the continuing cold war, a Soviet gesture toward the new U.S. Administration that cost Russia nothing. In political terms it was a first test of the Kennedy Administration’s ability to stay cool while the heat is on — and, from the moment that Ambassador Thompson entered Khrushchev’s office, the Administration passed its test handsomely.

Write to Katie Reilly at Katie.Reilly@time.com.