Rudy Giuliani, President Donald Trump's personal lawyer, uses his smartphone during a ceremony at the White House on May 30, 2018. American officials have expressed wonderment that Giuliani was running his "irregular channel" of diplomacy over open cell lines and communications apps penetrated by the Russians. Doug Mills, The New York Times

Rudy Giuliani, the former New York mayor at the center of the impeachment investigation into the conduct of Ukraine policy, makes a living selling cybersecurity advice through his companies. President Donald Trump even named him the administration’s first informal “cybersecurity adviser.”

But inside the National Security Council, officials expressed wonderment that Giuliani was running his “irregular channel” of Ukraine diplomacy over open cell lines and communications apps in Ukraine that the Russians have deeply penetrated.

In his testimony to the House impeachment inquiry, Tim Morrison, who is leaving as the National Security Council’s head of Europe and Russia, recalled expressing astonishment to William B. Taylor Jr., who was sitting in as the chief US diplomat in Ukraine, that the leaders of the “irregular channel” seemed to have little concern about revealing their conversations to Moscow.

“He and I discussed a lack of, shall we say, OPSEC, that much of Rudy’s discussions were happening over an unclassified cellphone or, perhaps as bad, WhatsApp messages, and therefore you can only imagine who else knew about them,” Morrison testified. OPSEC is the government’s shorthand for operational security.

He added: “I remember being focused on the fact that there were text messages, the fact that Rudy was having all of these phone calls over unclassified media,” he added. “And I found that to be highly problematic and indicative of someone who didn’t really understand how national security processes are run.”

Giuliani’s partner, Gordon D. Sondland, the US ambassador to the European Union, held an open cellphone conversation with Trump from a restaurant in Ukraine, apparently loud enough for his table mates to overhear. And Trump’s own cellphone use has led US intelligence officials to conclude that the Chinese — with whom he is negotiating a huge trade deal, among other sensitive topics — are doubtless privy to the president’s conversations.

But Ukraine is a particularly acute case. It is the country where the Russians have so deeply compromised the communications network that in 2014 they posted on the internet conversations between a top Obama administration diplomat, Victoria Nuland, and the US ambassador to Ukraine at the time, Geoffrey R. Pyatt. Their intent was to portray the Americans — not entirely inaccurately — as trying to manage the ouster of a corrupt, pro-Russian president of Ukraine.

The incident made Nuland, who left the State Department soon after Trump’s election, “Patient Zero” in the Russian information-warfare campaign against the United States, before Moscow’s interference in the US presidential election.

But it also served as a warning that if you go to Ukraine, stay off communications networks that Moscow wired.

That advice would seem to apply especially to Giuliani, who speaks around the world on cybersecurity issues. Ukraine was the petri dish for President Vladimir Putin of Russia, the place where he practiced the art of trying to change vote counts, initiating information warfare and, in two celebrated incidents, turning out the lights in parts of the country.

Giuliani, impeachment investigators were told, was Trump’s interlocutor with the new Ukrainian government about opening investigations into the president’s political opponents. The simultaneous suspension of $391 million in military aid to Ukraine, which some have testified was on Trump’s orders, fulfilled Moscow’s deepest wish at a moment of ground war in eastern Ukraine and a daily, grinding cyberwar in the capital.

It remains unknown why the Russians have not made any of these conversations public, assuming they possess them. But inside the intelligence agencies, the motives of Russian intelligence officers is a subject of heated speculation.

A former senior US intelligence official speculated that one explanation is that Giuliani and Sondland were essentially doing the Russians’ work for them. Holding up military aid — for whatever reason — assists the Russian “gray war” in eastern Ukraine and sows doubts in Kyiv that the United States is wholly supportive of Ukraine, a fear that many State Department and National Security Council officials have expressed in testimony.

But Giuliani also was stoking an unsubstantiated conspiracy theory that Putin has engaged in, suggesting that someone besides Russia — in this telling, Ukrainian hackers who now supposedly possess a server that once belonged to the Democratic National Committee — was responsible for the hacking that ran from 2015 to 2016.

Trump raised this possibility in his July 25 phone call with the new Ukrainian president, Volodymyr Zelenskiy. It was not the first time he had cast doubt on Russia’s involvement: In a call to a New York Times reporter moments after meeting Putin for the first time in Hamburg, Germany, in 2017, Trump endorsed Putin’s view that Russia is so good at cyberoperations that it would have never been caught. “That makes sense, doesn’t it?” he asked.

He expressed doubts again in 2018, in a news conference with Putin in Helsinki, Finland. That was only days after the Justice Department indicted a dozen Russian intelligence officers for their role in the hack; the administration will not say if it now believes that indictment was flawed because there is evidence that Ukranians were responsible.

Whether or not he believes Ukraine was involved, Giuliani certainly understood the risks of talking on open lines, particularly in a country with an active cyberwar.

As a former prosecutor, he knows what the United States and its adversaries can intercept. In more recent years, he has spoken around the world on cybersecurity challenges. And as the president’s lawyer, he was a clear target.

Giuliani said in a phone interview Monday that nothing he talked about on the phone or in texts was classified. “All of my conversations, I can say uniformly, were on an unclassified basis,” he said.

His findings about what happened in Ukraine were “generated from my own investigations” and had nothing to do with the US government, he said, until he was asked to talk with Kurt D. Volker, then the special envoy for Ukraine, in a conversation that is now part of the impeachment investigation. Volker will testify in public Tuesday.

Giuliani said that he never “conducted a shadow foreign policy, I conducted a defense of my client,” Trump. “The State Department apparatchiks are all upset that I intervened at all,” he said, adding that he was the victim of “wild accusations.”

Sondland is almost as complex a case. While he is new to diplomacy, he is the owner of a boutique set of hotels and certainly is not unaware of cybersecurity threats because the hotel industry is a major target, as Marriott learned a year ago.

But Sondland held a conversation with Trump last summer in a busy restaurant in Kyiv, surrounded by other US officials. Testimony indicates Trump’s voice was loud enough for others at the table to hear.

But the Russians most likely did not need a reservation because Ukraine’s phone system is deeply compromised. After the Nuland-Pyatt interception — which was held on an open line — embassy personnel have been told to assume that whatever they say routes back through Russian intelligence.



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