Following its established playbook, Russia has increasingly interfered in the politics of traditional opponents throughout the West in the hopes of undermining democracy and stability from within. Donald Trump was a political novice with a longstanding public admiration for Russian President Vladimir Putin and a penchant for advancing conspiracy theories. He espoused isolationist policies and had potentially compromising financial relationships with Kremlin-aligned oligarchs. He also had few apparent scruples and was running against a woman Putin considers among his main adversaries. Trump was simply an ideal candidate for the Kremlin to back. There is also reason to suspect that Russia began cultivating Trump as an asset long before his campaign for president, a common tactic the Kremlin pursues with people it suspects may be useful in the future.

Trump’s political rise

According to journalist Luke Harding, the author of Collusion: Secret Meetings, Dirty Money, and How Russia Helped Donald Trump Win, Russia has been interested in Trump since at least 1987, when Trump visited Moscow with the Russian ambassador to the United States, Yuri Dubinin. Harding has also reported on documents that reveal that Czechoslovakia spied on Trump in the 1970s and 1980s during his marriage to his Czechoslovakia-born first wife, Ivana Trump. According to Harding, the Czechoslovakian government specifically targeted Trump because of his high profile as a businessman and political ambitions. At the time, the Czechoslovakian government was known to have close ties to the KGB; it is unknown if they shared information on Trump specifically. As it relates to the 2016 election, though, the natural starting point for analyzing the relationship is Trump’s rise to political relevance in the early 2010s, largely as an outspoken—and outspokenly racist—crusader against President Barack Obama.

It is easy to forget that Trump initially supported Obama. In 2008, Trump—at the time a registered Democrat—praised Obama during the latter’s primary campaign, saying, “I think [Obama] has a chance to go down as a great president.” This praise continued into 2009, when he told Larry King that Obama was “totally a champion,” and 2010, when Trump wrote in his book Think Like a Champion that “Obama proved that determination combined with opportunity and intelligence can make things happen—and in an exceptional way.”

By 2011, however, Trump not only soured on Obama but was a leading proponent of the so-called birther movement. On March 23 of that year, Trump told the “Today” show he had “some real doubts” about Obama’s birthplace and had sent investigators to Hawaii to explore. On another “Today” appearance, on April 7, Trump again questioned Obama’s citizenship, falsely saying that Obama’s “grandmother in Kenya said he was born in Kenya, and she was there and witnessed the birth. He doesn’t have a birth certificate or he hasn’t shown it,” and that Obama had spent $2 million in legal fees “to get away from this issue.” Even after Obama released his birth certificate, Trump continued his birther crusade over the coming years, tweeting about Obama’s birthplace 73 times in 2012 alone. He only publicly acknowledged that Obama was born in the United States in September 2016, and then blamed Clinton for propagating the conspiracy theory—and, according to The New York Times, continued to privately question Obama’s citizenship.

How—and even whether—Trump came to believe Obama was born in Kenya remains unknown. Given that Trump was at the time flirting with running for president, some have suggested that he began espousing birtherism as a matter of political expediency, evincing a recognition that racism was a key tool for appealing to large segments of the Republican base. Regardless, Trump’s promotion of this conspiracy theory, and his concurrent political rise, would have been attractive to Russian intelligence. The Kremlin has a long and well-documented history of exploiting racial tensions in its efforts to influence politics abroad. Many of the European fringe parties Russia supports, such as France’s National Front, the U.K. Independence Party, and Alternative for Germany, employ thinly veiled or outright racist appeals. Russian bots and trolls on social media frequently aim to boost these tensions, as in January 2016, when Russian propagandists pushed false reports that German authorities had covered up evidence that a German teenager had been gang-raped by Muslim immigrants, and in June 2016, when they promoted a similar, and similarly unsubstantiated, story in Twin Falls, Idaho. Moreover, birtherism isn’t simply racist; it also fundamentally attacks American democracy, asserting that tens of millions of Americans were duped into electing an illegitimate president and suggesting a massive cover-up by the government and media.

Trump rode birtherism to political prominence in the early 2010s. He became an increasingly regular guest on Fox News and other conservative media outlets throughout the period, appearances that many analysts argue laid the groundwork for his presidential campaign. In early 2011, he publicly floated the possibility of running in the 2012 Republican primary; though some polls showed him as a strong contender, or even frontrunner, he ultimately chose not to run. Nevertheless, the 2012 election offered proof of his increasing influence within conservative politics, culminating in Republican nominee Mitt Romney actively seeking—and ultimately receiving—Trump’s endorsement, reportedly partly out of fear that Trump would launch a third-party candidacy. That such a famous American, with a hit television show, a massive Twitter following, a penchant for racist conspiracy theories, and a long history of friendly business relations with Russia, was gaining clout within the historically anti-Russia Republican Party would not have gone unnoticed in Moscow.

It’s likely no coincidence then that, according to the dossier compiled by former MI6 agent Christopher Steele, Trump began feeding Russian intelligence information around the same time. The dossier, citing four sources—two officials in Russia (a senior former intelligence official and a senior foreign ministry official) and two Russian expatriates—claims that Trump had a relationship with Russian intelligence for at least five years:

Speaking to a trusted compatriot in June 2016 sources A and B, a senior Russian Foreign Ministry figure and a former top level Russian intelligence officer still active inside the Kremlin respectively, the Russian authorities had been cultivating and supporting US Republican presidential candidate, Donald TRUMP for at least 5 years. . . .

Source close to TRUMP campaign however confirms regular exchange with Kremlin has existed for at least 8 years, including intelligence fed back to Russia on oligarchs’ activities in US.

The dossier’s allegation that Trump was providing information on Russian oligarchs living in his properties fits not only with how intelligence services operate—they often begin with such simple requests that targets do not realize they have become intelligence assets—but also with Russia’s efforts to keep tabs on its oligarchs, as well as Trump’s own track record of surveilling his buildings. Trump and members of his campaign named in the dossier have broadly denied its veracity, although they have not mounted any significant effort to discredit its individual allegations.

The Miss Universe Pageant trip

Trump’s trip to Moscow for the 2013 Miss Universe Pageant provided another ideal opportunity for Russia to cultivate him as an asset and to create the connections the Kremlin could then leverage in 2016. In planning and executing the pageant, Trump met with several individuals who would ultimately resurface during his presidential campaign, including Rob Goldstone, the music producer who arranged the June 9, 2016, meeting in Trump Tower; Azerbaijani Russian oligarch Aras Agalarov and his pop-star son Emin, on whose behalf Goldstone reached out to arrange the June 9 meeting; and Ike Kaveladze, an executive in the Agalarovs’ real estate company, whose actions formed the basis of a 2000 Government Accountability Office report on Russian money-laundering tactics and who attended the June 9 meeting. (The report does not allege any illegal behavior by Kaveladze, who has denied any wrongdoing.) Trump filmed a cameo appearance in the music video for Emin Agalarov’s song “In Another Life” at Moscow’s Ritz Carlton and rubbed elbows with other members of the Russian elite, such as Herman Gref, Russia’s former minister of economics and trade and the current CEO of Russia’s largest bank, Sberbank.

The Steele dossier describes the trip as a critical juncture in Russia’s cultivation of Trump as an asset. It is on this trip, Steele alleges, that Russia obtained kompromat on Trump in the form of a compromising video. This allegation, among the more explosive in the dossier, has been neither conclusively corroborated nor conclusively disproven. Trump denies that the event occurred; his personal bodyguard Keith Schiller testified before Congress that he actually turned down an offer from a Russian individual to “send five women” to Trump’s hotel room. Though Schiller presented the story as exculpatory, he also said he only stayed by the door to Trump’s hotel room for part of the night, leaving open the possibility that the encounter may have occurred after Schiller left. The episode also comports with Russia’s known tendency to produce kompromat on visiting government officials and business elite, often by bugging their hotel rooms and orchestrating embarrassing sexual encounters.

It is not unlikely, in fact, that there may be many instances of kompromat on Trump based on years of doing business in the region. For example, Putin has for the past several years exploited Russia’s oligarchs and their relationships with businesspeople and politicians in Western countries to advance the interests of the Kremlin. Trump’s tendency to court Russia-based financing for projects in not just the United States and Russia but also other former Soviet countries, including Georgia, Azerbaijan, and Kazakhstan, appears to have brought Trump into the orbit of many of the same oligarchs. The Trump Organization’s reputation for skimping on due diligence with regard to its clientele and business partners creates the possibility that one or more of his business partners may possess compromising information on his financial dealings along with the sexual kompromat described in the dossier.

Whether or not Russia obtained kompromat on Trump during the weekend of the Miss Universe Pageant, the trip clearly left Trump with a high opinion of Russia and Putin. In interviews and speeches during and after the trip, Trump boasted about his relationship with the country and its leader, alluding to receiving a gift from and speaking “indirectly—and directly—with President Putin, who could not have been nicer.” By the time he returned to the United States, Trump was primed for Russia to exploit him to undermine democracy in the 2016 election.


The Election

Chapter 4