Trump DOJ Let Secret Search of Giuliani’s iCloud Go Unchallenged

Trump Justice Department officials in Washington raised no concerns to Manhattan federal prosecutors when they said they wanted to covertly search Rudy Giuliani’s Apple iCloud account in late 2019, according to people familiar with the matter.

The Justice Department’s national security division was notified by Manhattan prosecutors because the former New York mayor was being investigated for possible undisclosed foreign lobbying stemming from his work in Ukraine, an issue which falls under the division’s purview.

Prosecutors didn’t need formal approval from Washington for the iCloud warrant, but senior officials could have raised questions or voiced concerns to Manhattan prosecutors that might have spurred them to reconsider the search or modify its scope, according to the people, who asked not to be identified because the discussions were private.

The lack of pushback in 2019 could undercut efforts by the personal lawyer to former President Donald Trump to cast both the iCloud search and the April 28 Federal Bureau of Investigation raids of his Manhattan home and office as the actions of politically biased prosecutors who “hate” him and his most famous client.

A spokesperson for the Manhattan U.S. attorney’s office, which is leading the probe, declined to comment, as did a spokesperson for the Justice Department in Washington. Robert Costello, Giuliani’s lawyer, said he didn’t know who was consulted in Washington prior to the 2019 iCloud search by Manhattan prosecutors.

Presidential Election

Other Justice Department officials may also have received notifications under policies governing searches that potentially raise attorney-client privilege questions. Prosecutors followed Justice Department policies with regard to Giuliani under both the Trump and Biden administrations, the people said.

Ryan Fayhee, a former lawyer with the Justice Department’s national security division who was not involved with the Giuliani investigation, said the fact that the iCloud search targeted a lawyer meant Washington was almost certainly involved.

“If the question is whether a search warrant could be carried out on Rudy Giuliani without the participation of Main Justice, the answer is definitely no,” said Fayhee.

Giuliani’s lawyers said Trump’s Justice Department did object to warrants to search Giuliani’s home and office, suggesting they were only approved after President Joe Biden’s appointees took over. But the department resisted the in-person raids primarily because they would have been very public and taken place around the time of the presidential election, according to a person familiar with the matter.

Giuliani’s lawyers took aim at the secret iCloud search in a 17-page court filing unsealed Monday in Manhattan federal court, claiming the justification offered by prosecutors -- that they feared the former New York mayor might destroy evidence or intimidate witnesses -- was unsupported and possibly misleading. They said they would try to block evidence including emails, voicemails and other stored communications from that search and the more recent raids.

The iCloud search was executed on Nov. 4, 2019, in the weeks after the arrest on campaign finance and other charges of Giuliani associates Lev Parnas and Igor Fruman, who helped him dig up dirt on Biden in Ukraine. Prosecutors sought Giuliani’s “address book information, call history and voicemails, text message content, email content, photos and videos, documents, search and web histories,” according to the defense filing.

Escalating Issue

It’s unclear if notification by Manhattan prosecutors sparked further discussion of the matter inside the Justice Department or how high it may have gone.

“If there are different views, then the issue will tend to escalate in the department,” said Daniel Braun, a former Justice Department official who wasn’t involved in the Giuliani investigation. “If it remains unresolved, it will go up to the deputy attorney general’s office.”

The warrant was accompanied by a protective order prohibiting Apple from disclosing to Giuliani that the contents of his iCloud account had been seized, according to court filings.

The iCloud search was only disclosed to Giuliani’s lawyers in a closed-door hearing in the days following the FBI raid last month. A similar covert search was executed on the iCloud and Google accounts belonging to Victoria Toensing, a Washington lawyer close to Trump, court records show. Her lawyers have also questioned the justification for the searches.

Prosecutors are investigating whether Giuliani orchestrated the ouster of Marie Yovanovitch, the then-U.S. ambassador to Ukraine, as a favor to certain Ukrainian interests in exchange for damaging information about Biden, a person familiar with the matter said last month. Trump’s attempt to get the Ukrainian government to launch an investigation of Biden led to his first impeachment.

The iCloud warrant covered a period running from May 2018 until November 2019, according to a person familiar with the matter. That timeframe dovetails with the earliest documented effort to lay the groundwork for Yovanovitch’s removal, according to the report of congressional investigators in Trump’s impeachment.

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