Rudolph W. 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 Trump even named him the administration’s first informal “cybersecurity adviser.”
But inside the National Security Council, officials expressed wonderment that Mr. 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 American 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,” Mr. 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.”
WhatsApp notes that its traffic is encrypted, meaning that even if it is intercepted in transit, it is of little use — which is why intelligence agencies, including the Russians, are working diligently to get inside phones to read the messages after they are deciphered.
But far less challenging is figuring out the message of Mr. Giuliani’s partner, Gordon D. Sondland, the American ambassador to the European Union, who held an open cellphone conversation with Mr. Trump from a restaurant in Ukraine, apparently loud enough for his table mates to overhear. And Mr. Trump’s own cellphone use has led American 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 United States 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 Ms. Nuland, who left the State Department soon after Mr. Trump’s election, “Patient Zero” in the Russian information-warfare campaign against the United States, before Moscow’s interference in the American 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 Mr. Giuliani, who speaks around the world on cybersecurity issues. Ukraine was the petri dish for President Vladimir V. 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.
Mr. Giuliani, impeachment investigators were told, was Mr. 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 Mr. 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 American intelligence official speculated that one explanation is that Mr. Giuliani and Mr. 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, also known as Kiev in the Russian transliteration, 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 Mr. Giuliani also was stoking an unsubstantiated conspiracy theory that Mr. 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.
Mr. Trump raised this possibility in his July 25 phone call with the new Ukrainian president, Volodymyr Zelensky. 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 Mr. Putin for the first time in Hamburg, Germany, in 2017, Mr. Trump endorsed Mr. 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 Mr. 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, Mr. 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.
Mr. 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 United States 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. Mr. Volker will testify in public on Tuesday.
Mr. Giuliani said that he never “conducted a shadow foreign policy, I conducted a defense of my client,” Mr. Trump. “The State Department apparatchiks are all upset that I intervened at all,” he said, adding that he was the victim of “wild accusations.”
Mr. 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, since the hotel industry is a major target, as Marriott learned a year ago.
But Mr. Sondland held a conversation with Mr. Trump last summer in a busy restaurant in Kyiv, surrounded by other American officials. Testimony indicates Mr. Trump’s voice was loud enough for others at the table to hear.
But in testimony released Monday night, David Holmes, a veteran Foreign Service officer who is posted to the American Embassy in Kyiv, and who witnessed the phone call between the president and Mr. Sondland, suggested that the Russians heard it even if they were not out on the town that night.
Asked if there was a risk of the Russians listening in, Mr. Holmes said, “I believe at least two of the three, if not all three of the mobile networks are owned by Russian companies, or have significant stakes in those.”
“We generally assume that mobile communications in Ukraine are being monitored,” he said.
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