Trump’s rude awakening as Giuliani makes matters worse for the president

The former New York mayor risks increasing his boss’s legal jeopardy

Former New York Mayor Rudy Giuliani speaks at the 2018 Iran Freedom Convention in Washington, U.S., May 5, 2018. Joshua Roberts / Reuters

When former New York mayor Rudy Giuliani joined Donald Trump’s legal team last month, the president needed help weathering the storm of allegations about a lucrative payment to an adult movie star, as well as the expanding reach of the Russia investigation. But his entry has only given rise to fresh legal questions.

In his first weeks, he has contradicted the president on the alleged $130,000 hush money payment made by his fixer to Stephanie Clifford, the actress known as Stormy Daniels who the president is accused of having an affair with, exasperated White House officials and apparently complicated Mr Trump’s legal strategy.

It didn’t get any easier at the weekend. As Mr Giuliani made a round of media appearances, he suggested that the president’s personal attorney may have paid off more women “if necessary” and that Mr Trump could refuse to answer questions posed by Robert Mueller, the special counsel investigating Russian meddling in the 2016 election.

In so doing, Mr Giuliani is displaying the pugilistic instincts so admired by the president. But he also risks increasing his boss’s legal jeopardy, according to analysts.

Alan Dershowitz, a Harvard law professor who has advised Mr Trump, said: “It seems to me that the approach last week of the Trump team plays into the hands of Mueller’s tactic to try, at any cost, to try to find technical violations against lower-ranking people so that they can be squeezed”.

The trouble began when Mr Giuliani was hired last month. He announced that Mr Trump had reimbursed Michael Cohen, his attorney, for a payment made to Ms Clifford, undermining the president’s claim that he had not known about it.

Mr Trump proceeded to publicly undermine his attorney on Friday, saying that he will "get his facts straight". He continued to make pointed remarks about his longtime friend. "There has been a lot of misinformation. I say, You know what? Learn before you speak. It's a lot easier".

But the saga continued on Sunday. In an interview with ABC’s This Week, Mr Giuliani managed to contradict his own statements about the payment, and said he would not rule out the president asserting his Fifth Amendment right against self-incrimination in the Russia investigation.

“I'm going to walk him into a prosecution for perjury like Martha Stewart?” he asked, invoking the example of the TV lifestyle guru convicted of lying to prosecutors in 2004 in an insider trading case.

His comments were greeted with glee by Michael Avenatti, the lawyer for Ms Daniels.

“I think it is obvious to the American people that this is a cover-up, that they are making it up as they go along,” he told ABC.

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Analysts are now wondering how long Mr Giuliani can last in the role.

It marks an extraordinary position for a man declared “America’s mayor” for his steadfast leadership as mayor of New York in the wake of the 9/11 terror attacks in 2001.

Like Mr Trump, he built his reputation in a city riddled with crime and Mob control during the 1980s, developing a brusque manner and headline-friendly patter as a prosecutor who specialised in organised and white-collar crime.

He was elected mayor in 1993 after running on a law and order ticket, promising to turn around a decaying city. His tough love and his tough police commissioner are credited with ridding New York of its reputation for violent crime, before he was catapulted on to the international stage in September 2001.

His own presidential ambitions came to naught in 2008 but he emerged as an early supporter of Mr Trump, frequently appearing as a warm-up act at campaign rallies in 2016.

Hank Sheinkopf, a veteran New York political operative, said Mr Trump needed a saviour, a role that the former mayor was only too happy to play.

“Donald Trump’s world is all about perception. It’s not about reality,” he said. “He thinks Giuliani is a prosecutor and all the prosecutors will pay attention and that therefore Rudy Giuliani can do something to make it all go away.

“That’s the New York way of thinking about it, that everything can be fixed if you just have the right person,” he continued. “The only problem with that is that it’s not how it works in the rest of the world”.

For his part, Mr Giuliani insists that the strategy is working and setting the agenda.

“Everybody’s reacting to us now, and I feel good about that because that’s what I came in to do,” he told The Washington Post after his TV appearance.

His comments suggest his role is as much public relations as it is legal.

Jeanne Zaino, professor of political science at Iona College, said there did seem to be a strategy at work.

She said it was unlikely Mr Giuliani had not consulted the president and that he could be laying a smokescreen to allow Mr Trump to plead the Fifth Amendment and refuse to answer investigator’s questions.

“One strategy is they go out on this media blitz to make the case to the public – or at least their base – that this is a witch hunt, that they are after the president and that the lawyers are telling him to take the fifth even if he doesn’t want to,” she said, “but he has to because this is unfair”.

Not everybody is convinced.

Joshua Dressler, professor of Law at Ohio State University, said Mr Giuliani had been tying himself up in knots trying to keep his story straight.

“My own speculation is that he has been for too long a Fox pundit, and as with pundits generally, they don't feel obligated to think about facts rather than simply pushing an agenda,” he said.

So, in pushing that agenda, Mr Giuliani may be pursuing a strategy straight out of the Trump playbook. But the president must now decide whether the man he hired to protect may actually be making matters worse.