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Rudy Giuliani’s Year of Living Dangerously

The Ukraine scandal that's engulfed the Trump White House is the culmination of the former New York City mayor's Eastern European misadventures.

Alex Wong/Getty Images

Nearly thirty years ago, then-President George H.W. Bush stood in Kyiv, in front of an auditorium of Soviet officials struggling to revive a flailing Soviet Union. Here was a golden opportunity for an American president to carry a torch for the independence movements bubbling up from Ukraine to Georgia to Kyrgyzstan. Bush, instead, backed the apparatchiks in the room. Tossing cold water on all those pushing to escape the USSR, Bush hinted that those demanding independence were doing little more than peddling “suicidal nationalism.” The Soviet Union—and Bush’s burgeoning partnership with then-Soviet Premier Mikhail Gorbachev—must remain. Ukraine’s independence could wait.   

Independence, nevertheless, arrived for Ukraine and the rest of the Soviet Union’s republics. And in those decades since Bush’s infamous “Chicken Kiev” speech, Americans have, by and large, learned that steering these post-communist nation-states onto pro-democratic, pro-transparency, pro-independence paths is in our national interests. Supporting the fracture of the Soviet empire was correct—and protecting those gains have been worth every penny. 

There have been slips along the way: The Clinton administration’s decision to back Russia’s brutal crackdown on Chechnya in the 1990s, which featured Bill Clinton bizarrely comparing Boris Yeltsin to Abraham Lincoln, comes to mind. More recently, good-time crime guy Paul Manafort reaped a king’s bounty buoying the most craven and homicidal actors in the entire region—a career that launched him to becoming Donald Trump’s 2016 campaign chair, and, from there, straight to prison. 

Nevertheless, Americans have worked to foster the democratic dreams of those nations which emerged from the shadow of the Soviet Union, eradicating corruption, encouraging civil society, and ensuring stability as they went. 

And then, a year ago, Rudy Giuliani showed up. His gadabout meddling has already done damage to hard-won gains. Years of progress made in smothering corruption, encouraging democracy, and combating Russian revanchism could all go up in smoke—all because Giuliani’s ghoulishness knows no depths, and his unalloyed illiberalism just so happens to benefit a president willing to go to unprecedented, and unsettling, lengths to assure re-election. 


Everything we’ve seen out of Ukraine over the past few weeks is demonstrative of how detrimental Giuliani has been to American interests in Eastern Europe. It’s difficult to overstate the damage he’s done in Ukraine, a nation that has sacrificed and suffered greatly in order to follow the kind of democratic model any previous American administration would have plied with praise. 

This is a country that managed to oust the hopelessly corrupt Viktor Yanukovych from its highest office not once, but twice over the past 15 years. This is a country on the wrong end of the first forced annexation that Europe has seen since the Second World War. Thousands of its citizens have perished in the half-decade-long struggle to achieve a Western dream: a Ukraine with close and lasting ties to the U.S.—a special relationship that would thrillingly demonstrate that Russian-style kleptocracy isn’t the only path a post-Soviet state can follow. 

But Giuliani, with Trump’s backing, is dragging Ukraine in the opposite direction by prodding the new Ukrainian government into launching a fabricated investigation into Joe Biden and his son, Hunter. As The Washington Post reported on Tuesday evening, numerous White House staffers had long been wondering what exactly Giuliani’s role in all of this has been. As one U.S. official said, “Rudy—he did all of this. This shitshow that we’re in—it’s him injecting himself into the process.”

It doesn’t even matter if Trump explicitly dangled the withholding of American aid in return for an investigation into the Bidens. As we already know, Ukrainian President Volodymyr Zelensky’s administration clearly came away with that impression—as would anyone, given that Trump reportedly pressured Zelensky to look into Biden some eight times in a single phone call, according to The Wall Street Journal. (Some of which the edited memo of Trump’s call with Zelensky, released Wednesday morning by the White House, hints at.) All the while, Giuliani has seized every bullhorn he can find in an effort to strongarm the Ukrainians into complying with this investigation. 

The alacrity by which Trump and Giuliani have made these unprecedented moves is matched only by the swiftness with which their demands have undercut American interests in Ukraine. Here, all of the worst fears of Trumpian foreign policy—its transactional underpinnings; its disdain of even the basics of democratic facades—are realized. Together, they threaten one of the core tenets of broader American geopolitical strategy: backing anyone trying to counter Russia’s hegemonic designs, especially those whose governments can boast democratic underpinnings. 

“Ukraine is now facing the prospect of becoming a double victim: on the one hand, a victim of Mr. Putin’s aggression; on the other, a victim of Mr. Trump’s desire to be re-elected at any price,” wrote New Europe Center president Alyona Getmanchuk in The New York Times this week. Or, as Daria Kaleniuk, the executive director of the Anti-Corruption Action Center—a leading light among Ukraine’s anti-corruption figures—added this month, there’s one “ultimate beneficiary” of Giuliani and Trump’s machinations: Russia.


Trump may be following Giuliani’s lead (which has already led the president straight to an impeachment inquiry), but Ukraine is far from the only country in Eastern Europe that Giuliani has laid his grubby paws on over the past year, all in pursuit of upending the gains made in fighting corruption, and the Kremlin. Look at Armenia, for instance. Just last year, Giuliani touched down in Yerevan—claiming, as recently stated with regard to his Biden exploit, to be working in his private capacity and not as Trump’s personal lawyer—in order to attend something called the Eurasian Week conference. While there, Giuliani decided that it would be a good idea to share a speaking stage with Sergei Glazyev, a sanctioned Russian official who had himself helped organize pro-Russian protests in Ukraine, and who has previously worked closely with American anti-Semites.

Giuliani’s speech was, as one attendee told this reporter, “total bullshit.” But while there, Giuliani not only became the highest-profile American to glad-hand with a sanctioned Russian official since the first rounds of sanctions rained down some five years ago—effectively undercutting the purpose of sanctions in the first place—he also distinguished himself as the most prominent American official to call for closer relations with the Eurasian Economic Union, one of the Kremlin’s primary geopolitical projects. Where previous officials like Hillary Clinton rightly pointed out that the Eurasian Economic Union was little more than a neo-imperial scheme aimed at shoring up Russian hegemony, Giuliani saw it as something for the U.S. to encourage—and to work with moving forward. 

Giuliani’s misadventures also brought his designs to Romania as well. Thanks to the efforts of a single-minded prosecutor, Romania’s anti-corruption efforts have gained significant headway in the past few years, a welcome change in one of the most corrupt countries of the European Union. Giuliani, however, had contrary thoughts—to his mind, Romania had been too effective in cleaning up the corruption corroding its public services. In a 2018 letter to Romania’s president, Giuliani wrote that Romania’s anti-corruption drive had led to “excesses,” and that there should be an amnesty for those caught up in the anti-corruption dragnet. Needless to say, Giuliani’s beliefs were in direct contradiction to American policy, and undercut the ongoing effort to counter dirty money and corrupt practices throughout the West.

Giuliani had never expressed an interest in Romanian anti-corruption efforts prior to his out-of-left-field letter, making that missive that much more curious. But it didn’t take long to connect the dots. Giuliani quickly admitted that he’d written the letter at the behest of former FBI Director Louis Freeh, whose consulting firm just so happened to be representing notorious Romanian clients on the wrong end of the anti-corruption drive. One of those buoyed by Giuliani’s efforts: Liviu Dragnea, the former head of Romania’s Social Democratic Party, who was recently jailed on charges of corruption. “Giuliani is a famous federal prosecutor of the United States, who has fought with the mafia and corruption, and whose moral and professional probity commands respect all over the world,” Dragnea claimed in response to Giuliani’s efforts. 

Dragnea’s encomium about Giuliani was ultimately of little use; earlier this month, the U.S. State Department barred the crooked politico from visiting the U.S., specifically citing his “involvement in significant corruption.” But by then, the damage—just as in Ukraine, just as in Armenia—had already been done. Despite his denials, Giuliani is perceived by all in his path as little more than a foot soldier for Trump. His autocrat-friendly outlook and his campaigns to undercut the effort to stem the tide of corruption across Eastern Europe are unfortunately taking root as America’s de facto position. 

Remarkably, all of Giuliani’s efforts have taken place only over the past 12 months. And given the eagerness with which Trump and his cronies have glommed onto some of these lines of attack, most especially with Biden and Ukraine, there’s little reason to think that Giuliani’s efforts across Eastern Europe will stop anytime soon. This is a travesty, verging on tragedy, for both those who live in the region, as well as for those involved in the larger effort to help the region onto a stable and democratic footing. 

Thirty years ago, a Republican administration tried to stall Ukrainians’ demands for independence, and for sovereignty. Today, a Republican administration—with Giuliani apparently as its mouthpiece—is trying to do much the same. It didn’t work then, and perhaps history will kindly repeat itself now. But the damage to America’s reputation, and to America’s interests, has begun. As long as Giuliani continues down the path he’s chosen, with an eager U.S. president in tow, the debasement won’t end anytime soon.