The questioning is an attempt to discover if the former president was knowingly taking legal advice from an inebriated attorney, reported Rolling Stone.
Federal investigators have asked witnesses if the former New York mayor was intoxicated on and after the 2020 election as Mr Trump allegedly tried to overturn his defeat to Joe Biden, sources told the magazine.
Prosecutors have also asked if Mr Trump ever talked with witnesses about Mr Giuliani’s drinking, and if Mr Trump ever claimed it impacted his decision-making or judgement.
They have also inquired if the former president was warned about Mr Giuliani’s “excessive drinking” while he was still in the White House.
And they have specifically asked witnesses how drunk they believed Mr Giuliani was while giving Mr Trump advice during key moments of his fight to remain in power, and if Mr Trump had been told about it.
Lawyers and witnesses who have been in the room with Mr Smith’s prosecutors say that the specific line of questioning could help demonstrate that the former president was implementing the advice of a person he knew to be under the influence of alcohol.
This could add to the case that Mr Trump behaved with willful recklessness as he tried to overturn Mr Biden’s legal victory.
This could help Mr Smith’s team undermine the argument of the expected “advice of counsel” defence that Mr Trump and his new lawyers could use in court.
“In order to rely upon an advice of counsel defense, the defendant has to, number one, have made full disclosure of all material facts to the attorney,” Mitchell Epner, a former Assistant United States Attorney for the District of New Jersey, told the magazine.
“That requires that the attorney understands what’s being told to them. If you know that your attorney is drunk, that does not count as making full disclosure of all material facts.”
And he added: “Now if, for example, Trump was getting two sets of advice from an attorney: one before 4 p.m. and when the attorney hadn’t been drinking and a second, much more aggressive set of advice after 4 p.m., when he had been drinking and this was a pattern, it would not be reasonable to rely on the drunk advice.”
The federal judge overseeing former President Donald Trump’s federal election interference case on Monday ordered that the case go to trial on 4 March 2024.
The ruling came after Mr Smith asked for the case to begin on 2 January, while Mr Trump has argued it should not begin until April 2026.
Judge Tanya Chutkan stated that in setting the March date she was giving Mr Trump’s lawyers “adequate time” to prepare while protecting “the public’s interest in seeing this case resolved in a timely manner.”
Mr Giuliani’s political adviser, Ted Goodman, attacked the Rolling Stone story in a statement to The Independent.
“One should always question a story that is completely reliant on anonymous sources. This false narrative by nameless sources has been contradicted by on-the-record witnesses,” he said.
“It’s unfortunate that political opponents would use a serious problem like alcoholism as part of their efforts to smear Mayor Rudy Giuliani—a man who took down the Mafia, cleaned up New York City and comforted the world following the September 11th terrorist attacks.”
Mr Goodman also pointed out the defence of Mr Giuliani by Roy Bailey, who says he was with the former mayor on Election Day 2020 and has denied he was drinking.
Mr Bailey served as Mr Trump’s National Finance Committee co-chairman and was in New York City with the Trump campaign on Election Day.