Bolton even warned his subordinates to avoid meetings in which Giuliani or his agenda might be raised. According to three sources with direct knowledge of the situation, Bolton told his team not to attend an Oval Office meeting May 23, 2019 with President Donald Trump following the inauguration of Ukrainian President Volodymyr Zelensky. The meeting, over Bolton’s objections, included former European Union Ambassador Gordon Sondland, former Energy Secretary Rick Perry, deputy national security adviser Charles Kupperman, Sen. Ron Johnson (R-WI) and ex-Special Envoy to Ukraine Kurt Volker. In the meeting, Trump told the group to “talk to Rudy,” who did not attend, about setting up a White House visit with Zelensky. Two sources said that the May directive from Bolton followed a series of warnings not to participate in meetings where Giuliani may attend.

The reluctance of Bolton’s NSC team to engage with Giuliani shows that as early as the spring of 2019, the former New York mayor was seen as a conduit for Russia’s evolving efforts to manipulate the forthcoming election. One former senior White House official recalled a series of discussions in the early days of 2019 that Russia was working on a scheme to leak “forged” or “fake” emails through intermediaries in the weeks leading up to the 2020 election. Officials viewed Giuliani as a possible target for such a leak, that person said. Another former official said Russia’s penetration of the servers of Ukranian energy company Burisma—where Hunter Biden once sat on the board—prompted “informed speculation among professionals that this would be the entree to fabricate material connecting Hunter Biden to corruption inside Burisma, and it wouldn’t take more than 10 percent truth.”