How Rudy Giuliani Became Trump’s Shadow Secretary of State

How Rudy Giuliani Became Trump’s Shadow Secretary of State

How Rudy Giuliani Became Trump’s Shadow Secretary of State

Through his travels from Iran to Ukraine, Giulani has become a walking, talking conflict-of-interest machine.



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Imagine, just for the sake of argument, that the president of the United States was an arrogant, information-challenged, would-be autocrat with a soft spot for authoritarian leaders from China, Russia, and North Korea to Egypt (“my favorite dictator”), Saudi Arabia, and Turkey. And then, suppose that very president, while hollowing out the State Department and slamming its diplomats as “Deep State” troublemakers, were to name a voluble wheeler-dealer attorney as his unofficial, freelance White House go-between with shady characters worldwide. Imagine further that the president would do an end run around the professionals of the US intelligence community—more Deep Staters, natch—and rely instead on conspiracy theories trundled back to Washington in that attorney’s briefcase.

Now, one last unimaginable thing, but humor me: Accept that the attorney in question went by the name of Rudy Giuliani.

That, of course, is a reasonable description of the state of America in 2020. Three-plus years into Donald Trump’s misshapen presidency, as the “adults” fled the room one by one or were pushed to the exits, the president was left with a rump collection of family loyalists and third-tier yes-people around him.

Rarely, if ever, do mainstream media types take a step back to survey the classic Star Wars bar–like crew of know-nothings, Bible-thumpers, and connivers who’ve been assembled as Trump’s “team” and their breathtaking incompetence and perfidy. Luckily, with Giuliani in the mix, there’s at least one figure so wildly over the top that analysts and pundits have heaped scorn or ridicule on his head, and often his alone, as a person so outrageously unfit, so borderline deranged, so nakedly in it for profit that it’s impossible to consider him without marveling at the tragicomedy of it all.

Since 2017, however, Rudy Giuliani has emerged as Trump’s shadow secretary of state with his hands in American foreign policy and politics from Iran to Russia, Turkey to Ukraine and beyond. That means anyone, anywhere in the world, with a few million bucks to proffer and an angle to pursue in Washington can avoid Secretary of State Mike Pompeo, the Christian-right über-hawk from Kansas, and sidle up instead to the former US Attorney from the Southern District of New York and mayor of New York City.

During most of 2019, as is well known to anyone who even casually followed the impeachment proceedings in Congress, Giuliani had a starring role in President Trump’s conspiracy-laden efforts to prove that Ukraine, not Russia, intervened in the 2016 election and that Joe Biden and his son Hunter were mixed up in something nefarious there. (To those in the reality-based world, of course, it was Russia, not Ukraine that meddled massively in 2016. And the Bidens, it’s clear, did nothing illegal in Kyiv.)

As we shall see, the Trump-Giuliani conspiracy theory about that country originated with and was “fertilized” by three individuals who’d earlier been caught up in Robert Mueller’s special counsel investigation of the White House: Lt. Gen. Michael Flynn, the disgraced former national security adviser in the White House; Paul Manafort, who chaired Trump’s election campaign; and Manafort’s Ukraine partner and ally, an apparent operative for Russia’s GRU intelligence service, Konstantin Kilimnik. In other words, the Trump-Giuliani Ukraine adventure did indeed get a boost from Vladimir Putin’s secret service and Moscow’s propaganda machine.

You’ll remember, perhaps, or maybe you’ve forgotten, that before Mike Pompeo was secretary of state, before his predecessor Rex (“Rexxon”) Tillerson even took the job, it looked for a while like Giuliani was going to get it. He and Donald Trump had been political friends-with-benefits since the mid-1990s, as evidenced by a cringe-worthy 2000 video of Trump placing his lips unbidden on Giuliani-in-drag’s “breast.” The former mayor had quietly sought to reposition himself as the reincarnation of Roy Cohn, the mob-connected lawyer who had been a mentor to the up-and-coming New York real estate tycoon. (“Where’s my Roy Cohn?”) It’s hardly surprising then that following Trump’s surprise victory in November 2016, Giuliani began lobbying hard for the secretary of state job. At the same time, he was fervently urging the president-elect not to select Never Trumper Mitt Romney for it. (Giuliani did, however, also endorse John Bolton, Washington’s warmonger in chief, for the job.)

Back in 2016, a week or so after the election, a New York Times editorial drily noted that the appointment of Giuliani as secretary of state “would be a dismal and potentially disastrous choice,” that he lacked “any substantive diplomatic experience and has demonstrated poor judgment throughout his career,” appeared “unhinged,” and would come with a “flurry of potential conflicts of interest.” And keep in mind that, back then, Giuliani was only getting started.

In recent years, much has been written, and accurately so, about the exodus of veteran diplomats—ambassadors to toilers in the ranks—from a gutted Foggy Bottom and its global outposts under both Tillerson and Pompeo. Writing last October for Foreign Affairs, for instance, former diplomat William Burns noted that fewer people took the department’s entrance exam in 2019 than in any year in previous decades. “Career diplomats,” wrote Burns, “are sidelined, with only one of 28 assistant secretary-rank positions filled by a Foreign Service officer, and more ambassadorships going to political appointees in this administration than in any in recent history.” He added: “One-fifth of ambassadorships remain unfilled, including critical posts.”

At the State Department, as one ambassador told The Hill, morale “is at a new low, although I am not sure it could fall much lower than where it has been for the past three years.” And that decline only accelerated after the humiliating dismissal of the US ambassador in Kyiv, Marie Yovanovitch, whose ouster was orchestrated by Giuliani.

To be sure, the State Department was never a progressive bastion, not during the Cold War years nor in the era when America was the global superpower. It is, nonetheless, the main vehicle for any president wishing to use the levers of diplomacy rather than the oft-chosen military option. Now, with the adults gone and the diplomats increasingly neutered, we’re left with Trump and Giuliani. Neither hawks nor doves, they’re vultures, viewing every country as part of a vast veldt where they can pick at carcasses of every sort for their own business or political gain.

How to Become a Shadow Secretary of State

Giuliani’s foreign policy portfolio extends far and wide, though it was in Ukraine—specifically with that country’s many corrupt, Russian-leaning oligarchs—that he rocketed to world attention and helped trigger the president’s impeachment. In his world travels, Giuliani has combined his roles as businessman, security consultant, political fixer, and the president’s personal attorney into a mishmash of overlapping identities. He has, in other words, become a kind of walking, talking conflict-of-interest machine.

Before zeroing in on Ukraine, however, let’s consider just a few of Giuliani’s other foreign ventures. Since leaving office as New York’s mayor, through Giuliani Partners, the Bracewell & Giuliani law partnership, and (after 2016) the giant law firm of Greenberg Traurig, along with Giuliani Security & Safety and Giuliani Capital Advisers, the former mayor has pulled in millions of dollars working on behalf of foreign clients, including highly controversial ones. Among those deals, contracts, and maneuvers, before and after Trump became president and hired his old friend Rudy to serve as his personal attorney in 2018, Giuliani has been involved in a far-flung series of deals: He’s been a paid lobbyist in Romania; had a cybersecurity contract in Qatar; had deals in Colombia, Argentina, and El Salvador; worked shadow diplomacy (with a business angle) with Venezuela’s President Nicolas Maduro; operated in Japan, Serbia, and Guatemala; and that only begins to tell the story.

Consider Turkey, starting in 2017. Back then, when Flynn was forced to resign after just a few weeks as national security adviser, it turned out that he had quietly (and without reporting it) been working on behalf of Turkey’s autocratic government, led by President Recep Tayyip Erdogan, during the 2016 election campaign. Erdogan was disturbed by the presence of a dissident, Fethullah Gulen, in the United States. As an unregistered advocate for Turkey, Flynn lobbied in 2016 to have the United States expel Gulen and send him back to Turkey. Early the next year, Flynn was gone, but no fear, Rudy Giuliani promptly took up the same cause. He began urging President Trump to extradite Gulen to Turkey, where Erdogan was accusing him of having plotted an attempted coup d’état. (In the end, Gulen wasn’t expelled.)

Given Giuliani’s ability to mix policy with business, you won’t be surprised to learn that he was also enmeshed in more lucrative efforts in Turkey. At around the same time, he was lobbying Trump to endorse a prisoner swap involving one of his clients, an Iranian-born Turkish gold trader named Reza Zarrab whom the FBI had arrested in 2016 on charges of money laundering and trying to do an end run around economic sanctions on Iran. According to The New York Times, Zarrab had been working with Halkbank, a major Turkish bank with close ties to Turkish Finance Minister Berat Albayrak, who is also President Erdogan’s son-in-law, to “funnel more than $10 billion in gold and cash to Iran.”

At first blush, it might seem odd for Giuliani to offer his services on behalf of an Iranian expat accused of trying to break US sanctions and whose family, it turned out, had close ties to former Iranian president Mahmoud Ahmadinejad. Curious, yes, but for Giuliani, business is business and there were bucks to be made. That he would use his connections to the Oval Office in an ultimately unsuccessful appeal for his client is even odder, given that Giuliani is otherwise a militant hard-liner when it comes to demanding the overthrow of the Iranian government.

Case in point: his long-time affiliation with the People’s Jihadists, otherwise known as the Mujaheddin-e-Khalq, or MEK. Like many of Giuliani’s escapades abroad, his efforts with MEK were a money-making project. Along with John Bolton, the late Senator John McCain, former national security adviser Jim Jones, and former attorney general Mike Mukasey, Giuliani has for years been affiliated with the MEK, making perhaps a dozen appearances, mostly paid speeches, at its conventions and rallies.

The MEK has almost no support inside Iran, not only because it’s conducted a terror campaign against that country’s top officials since 1981 but also because it operated with the backing of Iraqi autocrat Saddam Hussein during and after the Iran-Iraq war of the 1980s. It’s also widely regarded as a cult. Last year, in the midst of his anti–Joe Biden skulduggery in Ukraine, in his 11th appearance at an MEK confab, Giuliani traveled to Albania, of all places, where the group has established a military and political base. There, he called Trump “heroic” for “doing away with the reckless nuclear agreement and putting [Iran’s Islamic Revolutionary Guard Corps] on the terrorist list.”

In 2018, this reporter attended one of the MEK’s large-scale events, held at a hotel in midtown New York City. Gen. Jim Jones, who became an ultra-hawk after being ousted as President Obama’s national security adviser in 2010, spoke to the gathering first, noting proudly that he is supposedly on a list of people the government in Tehran plans to assassinate.

Rising to speak after Jones, Giuliani seemed jealous. “I hope I say enough offensive things that they’ll put me on that list to kill me,” he commented. Needless to say, both Jones and Giuliani are still alive and kicking, and there’s no evidence that either one is on any Iranian kill list. However, thanks in part to Giuliani’s hard-line, anti-Iran advice to the president, that country’s top general, Qassim Suleimani, was indeed placed on a presidential kill list and drone assassinated as 2020 began.

And Then There Was Ukraine

It was, of course, in connection with Ukraine that Giuliani’s freelancing came to the world’s attention. In the House Permanent Select Committee on Intelligence’s impeachment report, his name is mentioned about 160 times. He’s cited, first and foremost because, in that infamous “perfect” July 2019 phone call of his, Trump asked Ukrainian President Volodymyr Zelensky to work through him; because the former mayor was the primary organizer of the smear campaign against the actual ambassador to Ukraine, Marie Yovanovitch, who was subsequently fired; and because it was he who, starting as early as May 2019, masterminded a months-long political witch hunt against the Bidens, demanding over and over that Ukraine carry out an ersatz investigation of the man the president then expected to be his chief 2020 election opponent.

Numerous figures, including Ambassador Bill Taylor, who succeeded Yovanovitch at the US embassy in Kyiv, would express dismay over Giuliani’s role as the “irregular” channel for the Trump administration’s Ukraine policy—the “Giuliani factor,” as Ambassador to NATO Kurt Volker called it. The story of how all this led to the president’s impeachment is too well known to be rehashed here.

The Joe Biden/Hunter Biden part of the Ukraine story was straightforward enough in its own way. Far more complicated and troubling was the adherence of the president and Giuliani to a weird conspiracy theory that Ukraine, not Russia, used its intelligence service to try to sway the 2016 election. According to various official reports and in the opinion of virtually every expert who’s studied the matter, it was Russia that intervened to boost Trump’s election campaign. According to Trump and Giuliani, however, Ukraine meddled in 2016 on behalf of Hillary Clinton and indeed, they argue, the actual Democratic National Committee server somehow found its way to Kyiv, thanks to a computer security firm called CrowdStrike, which Trump claimed was owned by a wealthy Ukrainian. (It is not.)

Naturally enough, this Trump-Giuliani theory was nonsense, but according to The Washington Post, it had its origins—perhaps not surprisingly—in propaganda generated in Moscow. The Post reported that Paul Manafort, Michael Flynn, and Manafort’s partner, Konstantin Kilimnik, “played a role in convincing Trump that Russia did not actually interfere in the 2016 U.S. presidential election, despite what both Mueller and the U.S. intelligence community have concluded, and that it was actually Ukraine.”

According to Rick Gates, Manafort’s deputy, the Ukraine conspiracy theory originated with his boss, who “parroted” the line from Kilimnik. And both Manafort and Kilimnik—who was indicted by Mueller—had ties to Moscow operatives and pro-Russian forces in Ukraine, while Kilimnik himself was identified by Mueller and the FBI as part of Russia’s GRU.

As the Post concluded: “So we have two men [Manafort and Flynn] who have been convicted of offenses related to their Russia ties, have both lied to investigators about their interactions with Russian interests, and who apparently played a significant role in pushing a theory to Trump that Russia did not actually interfere in the 2016 election. They instead pointed the finger at Russia’s nemesis, Ukraine, and that has apparently stuck with Trump for more than three years.”

And it was that line that would be spread eagerly by pro-Trump writers like The Hill’s John Solomon. In a review of Solomon’s pieces, released this month, The Hill’s editors analyzed 14 of his columns with titles like “As Russian collusion fades, Ukraine plot to help Clinton emerges.” In doing so, they found numerous troubling facts about Solomon, his sources, and his overall reporting. As the Hill report put it:

Giuliani has indicated he was a key source of information for Solomon on Ukraine, telling The New York Times in November 2019 that he turned over information about the Bidens earlier in the year to Solomon.

“I really turned my stuff over to John Solomon,” Giuliani said.

The former New York City mayor later told The New Yorker he encouraged Solomon to highlight information on the Bidens and Yovanovitch, stating, “I said, ‘John, let’s make this as prominent as possible,’ adding, ‘I’ll go on TV. You go on TV. You do columns.’”

Two colorful characters who acted as Giuliani’s Ukraine go-betweens, Lev Parnas, and Igor Fruman, have been indicted on conspiracy charges and, according to Fortune, Giuliani, too, could be indicted in that case. As CNN noted in January, it’s nearly unheard of for a US Attorney’s office—in this case the one for the Southern District of New York (SDNY)—to end up indicting a former US attorney who led the same district. CNN added: “The SDNY community has watched in disbelief as Giuliani continues to seek the spotlight even as the investigation has unfolded and expanded into new fronts on a nearly weekly basis. The impeachment inquiry has also unleashed new evidence regarding his role performing shadow diplomacy on behalf of President Donald Trump as recently as [mid-January].”

Indeed, Giuliani is still at it. In concert with a collection of corrupt ex-prosecutors in Ukraine and in his ongoing role as shadow secretary of state cum intelligence chief, Giuliani is still gathering conspiracy-riddled information on the Bidens in Kyiv—and Attorney General William Barr has obligingly created an “intake process in the field” to absorb Giuliani’s work product straight into the Department of Justice. One thing is guaranteed: “Secretary of State” Giuliani will have a clear field in Kyiv, since Ambassador Taylor was unceremoniously fired on January 1st of this year.

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