target through monitoring communications of other people who interact with that target. In a December 2019 opinion piece, former FBI director, CIA director and federal judge William Webster wrote of "a dire threat to the rule of law in the country I love". In addition to chastising President Trump and attorney general Bill Barr, Webster wrote he was "profoundly disappointed in another longtime, respected friend, Rudy Giuliani" because his "activities of late concerning Ukraine have, at a minimum, failed the smell test of propriety". Since 2005, Webster had served as the chair of the Homeland Security Advisory Council. NBC News reported in December 2020 that SDNY investigators, which were reported in late 2019 to be investigating Giuliani's activities, had discussed with Justice Department officials in Washington the possibility of acquiring Giuliani's emails, which might require headquarters approval due to protection by attorney–client privilege. The New York Times reported in February 2021 that the SDNY had requested a search warrant of Giuliani's electronic records in summer 2020, but were met with resistance from high-level political appointees in the Washington headquarters, ostensibly because the election was near, while career officials were supportive of the search warrant. The Justice Department generally avoids taking significant actions relating to political figures that might become public within sixty days of an election. Senior political appointees nevertheless opposed the effort after the election, noting Giuliani played a leading role in challenging the election results. The officials deferred the matter to the incoming Biden administration. Federal investigators in Manhattan executed search warrants on the early morning of April 28, 2021, at Giuliani's office and Upper East Side apartment, seizing his electronic devices and searching the apartment. FBI agents also executed a search warrant that day on Toensing's Washington, D.C.-area home and confiscated her cellphone. In April 2021, Giuliani's attorney said investigators told him they had searched his client's iCloud account beginning in late 2019, later arguing to a judge that the search was illegal and so the subsequent raid on Giuliani's properties was "fruit of this poisoned tree," demanding to review documents justifying the iCloud search. In May 2021, the SDNY confirmed in a court filing that in late 2019 it obtained search warrants for Giuliani's iCloud account, and that of Toensing, as part of "an ongoing, multi-year grand jury investigation into conduct involving Giuliani, Toensing, and others," and argued that attorneys for Giuliani and Toensing were not