The 76-year-old stepped out on Saturday in Manhattan with Dr Maria Ryan – his rumored girlfriend and former alleged mistress.
Giuliani, who was wearing a face mask, was seen arriving at a cafe close to his apartment on the Upper East Side where he was met by Ryan.
The pair arrived in separate cars but left the cafe together. Ryan was spotted behind the wheel of the car as they left.
Giuliani appeared to be accompanied by an unidentified younger woman as they made their way to the car.
He could be seen going through what appeared to files while sitting in the front seat.
Ryan, who stepped down as CEO of a New Hampshire hospital in December, has reportedly been dating Trump’s personal lawyer since 2018.
Giuliani has previously denied allegations he had an affair with Ryan while he was still married to his third wife Judy Giuliani.
Rudy Giuliani was spotted leaving a cafe on the Upper East Side where he dined with his alleged girlfriend Dr Maria Ryan on Saturday
Dr Maria Ryan met Giuliani at the cafe after arriving there separately. The pair left in the same vehicle after emerging at different times
Ryan was named as Giuliani’s alleged mistress in court documents filed back in 2018 amid his divorce from Judy.
Giuliani denied there was any proof of an affair despite being spotted spending the night together at an upstate New York hotel.
The pair were pictured attending a White House dinner hosted by President Trump in 2019.
Giuliani referred to Ryan as an ‘associate’ earlier this year when he admitted to billing Trump $20,000 per day to dispute the election results – despite previously denying demanding money for his legal services.
He told the New York Times in January that his associate – who he named as Maria Ryan – had sent an email to at least three Trump campaign officials in November demanding payment.
Their sighting together came just days after the FBI executed a search warrant on his Manhattan home as part of an investigation into his dealings in Ukraine.
Giuliani, who is the former US Attorney for the Southern District of New York and former mayor of NYC, has already slammed the 6am raid as ‘illegal’ and ‘unconstitutional’.
He has sought to discredit the federal investigation, saying the raid – which he said involved seven FBI agents – was unnecessary because he offered for two years to provide prosecutors his electronic devices and to ‘talk it over with them’.
‘They won’t explain to me what they’re looking into for two years,’ Giuliani told Fox News’ Tucker Carlson.
Giuliani’s lawyer, Robert Costello, has previously said proposed meetings between investigators and Giuliani’s legal team didn’t take place because prosecutors wouldn’t agree to a precondition that they first disclose more about the probe.
According to the warrant, investigators are seeking to review Giuliani’s phones and computers for communications with more than a dozen people, including a high-ranking prosecutor in Ukraine.
They also are searching for communications with any U.S. government official or employee relating to Marie Yovanovitch, the US ambassador to Ukraine who was ousted by the Trump administration in 2019, the warrant said.
Agents seized more than 10 cell phones and computers from Giuliani’s Manhattan apartment and office in raids.
The federal probe is examining Giuliani’s interactions with Ukrainian figures and whether he violated a federal law that governs lobbying on behalf of foreign countries or entities.
Giuliani has insisted that all of his activities in Ukraine were conducted on behalf of former President Donald Trump.
At the time, Giuliani was leading a campaign to press Ukraine for an investigation into now-President Joe Biden and his son Hunter.
It has since emerged that Trump’s allies are deeply troubled by the Giuliani raid.
Their fears emerged as a transcript of a conversation between Giuliani and a Ukrainian official was published, laying bare what seems to be the substance of the FBI’s investigation.
A transcript of his July 2019 call, which took place between Giuliani and Andriy Yermak, who at the time was newly-elected President Volodymyr Zelensky’s top foreign policy advisor, was published by BuzzFeed on Friday.
Giuliani attempts, on the call, to establish a working relationship between Kiev and Washington DC – bypassing the usual State Department channels to speak directly for Trump, although he is at pains to emphasize that he cannot speak for his boss.
He is particularly emphatic that the new president should investigate Biden, who, while serving as vice president, had pushed for the firing of the country’s chief prosecutor, Viktor Shokin.
Shokin, who was seen with suspicion in the West, was fired in March 2016, as part of an anti-corruption initiative developed by the State Department and coordinated with the European Union and the International Monetary Fund.
Giuliani seeks an investigation, and wants Zelensky to publicly accuse Biden.
He also wants Ukraine to investigate possible interference in the election, and back the idea that Ukraine – not Russia – could have tried to tip the scales in favor of Trump.
‘All we need from the president is to say: I’m gonna put an honest prosecutor in charge, he’s gonna investigate and dig up the evidence, that presently exists and is there any other evidence about involvement of the 2016 election,’ Giuliani tells Yermak.
‘And then the Biden thing has to be run out.’
Giuliani says: ‘He offered Poroshenko a $1.2 billion loan guarantee, critical to Poroshenko’s success as president, in exchange for getting rid of a prosecutor general, that he didn’t wanna get rid of.
‘Somebody in Ukraine’s gotta take that seriously.’
Giuliani then turns to Hunter Biden’s energy firm, Burisma.
As part of a campaign to discredit Joe Biden and accuse him of influence peddling, Giuliani was keen for details of Hunter’s work on the board of the company.
‘That investigation of Burisma has been started, discontinued, started and discontinued about three times,’ Giuliani complained.
He also issued a bizarre warning to the new president, via his aide, saying: ‘What I wanted to tell the president is: be careful.
‘Probably it’s a little arrogant to say that. I shouldn’t say that about being careful.
‘But just as a person interested: be careful of the people around you, because… they can very easily… they can very easily get you into trouble.’
He did not provide more detail.