Back in the 1990s, Henry Kissinger, the legendary former U.S. secretary of state-turned-global consultant, encountered an intriguing young Russian and proceeded to ask him a litany of questions about his background.

“I worked in intelligence,” Vladimir Putin finally told him, according to “First Person,” a 2000 autobiography cobbled together from hours of interviews with the then-unfamiliar Russian leader. To which Kissinger replied: “All decent people got their start in intelligence. I did, too.”


As Putin climbed the ranks in the Kremlin, eventually becoming the autocratic president he is today, he and Kissinger kept up a warm rapport even as the United States and Russia grew further apart. Kissinger is one of the few Americans to meet frequently with Putin, one former U.S. ambassador recently recalled -- along with movie star Steven Seagal and ExxonMobil CEO Rex Tillerson, the likely next secretary of state.

Now, as Donald Trump signals that he wants a more cooperative relationship with Moscow, the 93-year-old Kissinger is positioning himself as a potential intermediary — meeting with the president-elect in private and flattering him in public. Like Trump, Kissinger has also cast doubt on intelligence agencies’ conclusion that Russia sought to sway the election in Trump's favor, telling a recent interviewer: “They were hacking, but the use they allegedly made of this hacking eludes me.”

Some have expressed surprise that the urbane, cerebral former top diplomat would have any affinity for the brash, shoot-from-the-lip Trump. But seasoned Kissinger watchers say it’s vintage behavior for a foreign policy realist who has cozied up to all sorts of kings and presidents for decades. And in fact, Trump may wind up an ideal vessel for Kissinger -- the architect of detente with the Soviets in the 1970s -- to realize his longstanding goal of warmer ties between the two Cold War adversaries.

For years, Kissinger has argued that promoting a greater balance of power between the U.S. and Russia would improve global stability. But skeptics fear this approach will sacrifice other values and reward bad behavior by the Kremlin, including its alleged election meddling, its invasion of Ukraine and its support for Syrian dictator Bashar Assad. There’s also the question of how Kissinger himself would personally benefit from a new reset with Russia: Aside from the reputational boost of having easy access to two major world leaders, the former secretary of state's secretive consulting firm, Kissinger Associates Inc., could get a bump in business.

“I think Kissinger is preparing a diplomatic offensive,” said Marcel H. Van Herpen, a Russia specialist and Putin critic who directs the Cicero Foundation, a Dutch think tank. “He’s a realist. The most important thing for him is international equilibrium, and there’s no talk of human rights or democracy.”

Trump aides did not offer a comment on the president-elect’s relationship with Kissinger, who served as secretary of state and national security adviser in the administrations of Richard Nixon and Gerald Ford. But sources familiar with the transition effort say the Manhattan real estate mogul is fascinated by Kissinger as well as other Republican elder statesmen, such as Robert Gates and Condoleezza Rice, to whom he has turned for advice on policy and staffing.

Kissinger and Trump have chatted on multiple occasions, including during at least one face-to-face meeting since the Nov. 8 election. And Kissinger, to the surprise of many in the broader foreign policy establishment, has spoken admiringly — albeit carefully — about the Trump phenomenon. Even after Trump spoke directly with the president of Taiwan -- a move that angered Beijing and went against the One China policy that Kissinger negotiated in the 1970s -- the former secretary of state expressed confidence Trump would uphold U.S. diplomatic traditions with the Chinese.

Associates of Kissinger also are in touch with others in the Trump orbit. One top Kissinger aide, Thomas Graham, is being floated among lower-level transition interlocutors as a potential ambassador to Russia, according to a source familiar with the conversations.

Graham met with House Foreign Affairs Committee staffers on Capitol Hill earlier this month, accompanied by other Russia observers, according to four people familiar with the session. Graham also sought meetings in the Senate. Graham appeared to be trying to identify people who shared similar outlooks on Russia and had connections to the Trump transition, three of the people said.

Kissinger also has praised Trump's choice of Tillerson as the next secretary of state, dismissing worries that the ExxonMobil chief is too close to the Kremlin. “He would be useless at the head of Exxon if he was not friendly with Russia… I don’t hear those concerns at all," Kissinger said at an event in Manhattan. "Nobody can meet every single qualification for secretary of state. I think it’s a good appointment.”

Kissinger Associates doesn’t disclose its clients under U.S. lobbying laws. The firm once threatened to sue Congress to resist a subpoena for its client list. It has in the past advised American Express, Anheuser-Busch, Coca-Cola and Daewoo. But the firm does belong to the U.S.-Russia Business Council, a trade group that includes ExxonMobil, JPMorgan Chase and Pfizer.

A person familiar with the Trump team's national security planning warned against reading too much into the Trump-Kissinger relationship. The president-elect, the person said, "admires the reputation and the gravitas but isn't necessarily persuaded by the Kissingerian worldview."

That may be true when it comes to China, a frequent subject of Trump’s ire, and the need to maintain a strong NATO, whose usefulness Trump has repeatedly questioned. But Trump's desire for warmer ties with Russia has been one of the more consistent stances he's taken, and he could find alignment with Kissinger.

POLITICO's attempts to reach Kissinger did not succeed this past week. But despite his unsavory reputation among human rights advocates -- who recite a litany of moral offenses from Vietnam to Bangladesh -- presidents of both political parties have sought Kissinger's advice for the past 40 years, and he's been eager to oblige.

During the final years of the George W. Bush administration, as relations with Moscow were souring, Kissinger teamed up with Evgeny Primakov, the former Russian prime minister and head of the Russian Chamber of Commerce and Industry, to co-chair a working group focused on bilateral relations between the U.S. and Russia. Putin blessed the venture. According to Kissinger, Bush, too, hoped the initiative would yield positive results, even assembling members of his national security team to learn about its work in 2008. But the payoff was modest, at best: Russia sent troops into the former Soviet state of Georgia in August 2008, angering the Bush administration, which imposed limited sanctions.

When Barack Obama took over the presidency from Bush, he sought Kissinger’s help on how to deal with Putin. A 2009 meeting between Kissinger and Putin helped lay the groundwork for a new arms-control pact as part of Obama’s effort to “reset” Russian relations. Kissinger remained involved in arms negotiations through 2010, according to then-Secretary of State Hillary Clinton’s emails released by the State Department. But ultimately that reset failed as well, for reasons that include Putin's frustrations over U.S. support of NATO and European Union expansion, which he believed threatened Russian influence in countries such as Ukraine.

In a February speech honoring Primakov, who died last year, Kissinger sketched out his view of the way U.S.-Russian relations should work. "The long-term interests of both countries call for a world that transforms the contemporary turbulence and flux into a new equilibrium which is increasingly multi-polar and globalized," he said. "Russia should be perceived as an essential element of any new global equilibrium, not primarily as a threat to the United States.”

President Richard Nixon talks with Secretary of State Henry Kissinger about the Middle East crisis in 1973.

As for Ukraine, which lost its Crimea region to Russian annexation in 2014 and is still fighting Russian-backed separatists in its east, Kissinger argued that it shouldn’t be invited to join the West outright. "Ukraine needs to be embedded in the structure of European and international security architecture in such a way that it serves as a bridge between Russia and the West, rather than as an outpost of either side," he said.

In Syria, he likewise called for the U.S. to cooperate with Russia, which has used indiscriminate air power to help Assad crush rebel forces. "Compatible U.S.-Russian efforts coordinated with other major powers could create a pattern for peaceful solutions in the Middle East and perhaps elsewhere,” he advised at the time.

Steven Pifer, a former U.S. ambassador to Ukraine, noted that it's not yet clear how far Trump will go to accommodate Russia. The president-elect’s pick for defense secretary is James Mattis, a retired Marine general who views Moscow as a major threat. And Trump, who prides himself on his deal-making skills, may ultimately conclude that Russia has little to offer.

“Does Trump get to a better relationship with Russia without getting something for it in terms of better behavior?" Pifer asked. "If we’re prepared to accept what they’re doing in Syria, Crimea, and Eastern Ukraine, we can have a better relationship, but we’ve sacrificed other interests and it’s not clear what we get for that.”

In an interview with CBS News that aired earlier this month, Kissinger spoke of both Trump and Putin in terms that suggested a sense of respect, if not necessarily awe.

Trump, Kissinger said, "has the possibility of going down in history as a very considerable president.” Because of perceptions that Obama weakened America's influence abroad, "one could imagine that something remarkable and new emerges” out of a Trump administration," he said. "I’m not saying it will. I’m saying it’s an extraordinary opportunity.”

Putin, meanwhile, is a "character out of Dostoyevsky,” Kissinger said, a reference to the 19th-century author who chronicled the often bleak lives of Russians in novels such as "Crime and Punishment" and "The Idiot." “He is a man with a great sense of connection, an inward connection, to Russian history as he sees it,” Kissinger said of Putin.

The Kremlin took it as a compliment. “Kissinger knows our country really well, he knows our writers and our philosophers so such comparisons from him are quite positive,” a spokesman for the Russian government said, adding that Kissinger "has deep knowledge, not superficial.”

