Rudy Giuliani, the former New York mayor at the centre 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 Mr Giuliani was running his “irregular channel” of Ukraine diplomacy over open cell lines and communications apps 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,” Mr Morrison testified.
Opsec is the government’s shorthand for operational security.
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 Mr 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.
Mr Giuliani, impeachment investigators were told, was the US president’s interlocutor with the new Ukrainian government about opening investigations into Mr Trump’s political opponents.
The simultaneous suspension of $391m (£302m) 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.
A former senior US intelligence official speculated one explanation is that Mr Giuliani and Mr Sondland were essentially doing the Russians’ work for them.