Scott Horton is a practicing attorney, lecturer in law at Columbia Law School, and a contributing editor at Harper’s magazine, where he writes on national security and legal issues, and where he met yours truly. Three days ago I called him to ask if he’d do a Six Questions interview about former MAGA World superstar Rudy Giuliani, whose law firm Scott once worked at. As luck and good fortune would have it, just yesterday morning federal investigators “executed search warrants at the Manhattan home and office of Rudy Giuliani, former President Donald Trump’s attorney,” according to this story by The Associated Press. “The former New York City mayor has been under investigation for several years over his business dealings in Ukraine. Details of the searches were not immediately available, but it comes as the Justice Department continues its investigation into the former New York City mayor and staunch Trump ally.”
So my interview request was perfectly timed and Scott, who knows more about Giuliani than anyone I know, was the perfect person for the job. Hence, without further ado, here you go. Enjoy!
1. Rudy Giuliani was certainly one of the more flamboyant and ethically-challenged figures from the Trump/MAGA era. There was a period when Giuliani was quite well-regarded, at least in the media. Was his previous reputation unwarranted? Or were the Trump years an aberration?
In the mid-1980’s, I went to work for Rudy’s old law firm, worked for his mentor and with many of his friends, and had several encounters with him. I was impressed with Rudy’s record as a prosecutor and at the Justice Department; impressed mostly with his level of energy and his engaging, if somewhat acid, personality. But over the years I heard plenty of stories about Rudy’s career and law practice. He was a superstar with a high public profile. But his professional habits worried many of his partners. He had encounters with young associates, particularly women, that produced friction and complaints. He had a shoot-from-the-hip approach to dispensing legal advice that many considered dangerous. He tended to view everything as just an extension of partisan politics. He rarely showed much respect or deference for his partners. In sum many, but not all, of the current knocks on Rudy were evident forty years ago.
2. Let’s turn to the Trump years. What do you consider to be one of the most troubling of his activities?
Rudy’s style is the starting point. Much of what he did was ambiguous. Was he Trump’s lawyer or not? Was he representing Trump or just making comments? Was he a television commentator or an attorney? It was never clear, and to make matters worse, at times he said he was Trump’s lawyer and a spokesman from the White House would deny it. But the most troubling stuff probably has to do with the subject of the subpoena that the FBI just executed on Rudy: his Ukraine activities linked to the Trump 2020 election campaign.
3. Putting aside the ethics of Giuliani’s actions, were Hunter Biden’s activities in Ukraine, and elsewhere overseas, cause for concern?
High profile political figures often have offspring who embarrass them or even do something corrupt. Particularly when the children are adults, that’s fair game for a political campaign. In that sense, there was nothing wrong with Rudy going after Hunter Biden and trying to find some dirt on Joe Biden through that route.
That’s not the issue. The issue came when Giuliani started dealing with figures clearly tied to Russian intelligence as a source for the dirt and when he began trying to use U.S. diplomatic leverage for the benefit of the Trump campaign, which led to Trump being impeached.
Giuliani had well-documented dealings with Dmytro Firtash, a Ukrainian oligarch now under indictment in the U.S., with ties to Russian intelligence and a record of doing the Kremlin’s dirty work, and with Andrey Derkach, a man officially labeled a Russian agent by the U.S. government under Trump. Did Rudy and his co-counsel Victoria Toensing and Joe DiGenova promise Firtash that they could get the charges the Justice Department brought against him quashed for a fee? What were the financial dealings they had with Firtash? Rudy was given warnings from people in the Trump administration about who Firtash and Derkach were; he chose to ignore them. These dealings raised huge legal problems about acting for a foreign government, indeed, a hostile foreign government—the law requires disclosures that Rudy didn’t make, and which are far more serious in the context of a high-profile federal election. That’s beyond the ethics issues for an attorney, and the fact that it just wasn’t a very smart thing to do in the first place. But if we had to use one adjective to describe Rudy’s Ukraine work, it would be “reckless.”
4. What’s another example of Giuliani’s disturbing actions from the Trump era?
Rudy’s highest profile gig was as the leader of Trump’s post-election efforts to challenge the outcome. Two things I’d say here: one is his work was incredibly incompetent. To lose so many lawsuits over so many technical issues is almost unprecedented. Election law experts I have spoken with say it points to a lack of sophistication about how election law works on many different levels, including the timing for complaints, bringing them before the right courts, and presenting the right facts in the right form. Had he managed this competently, he would almost certainly have succeeded with some challenges, though it seems almost unimaginable at this point that he could have altered the outcome.
The second point is that Giuliani was being a TV lawyer, not a real lawyer. He was making claims to the cameras that he couldn’t prove, and didn’t even try to prove, in court. This fueled his court losses and angered many of the courts, most of which were filled with Republican judges whose attitudes were anything but hostile to the Trump campaign. It is not a crime to do what Rudy did, but it probably is a serious violation of the canons of professional responsibility binding on lawyers. And this has landed Rudy in trouble with the bar ethics authorities. A formal case against him is now pending. That will percolate along quietly for a while, but it doesn’t look good for him. He’ll be very lucky to escape with chastisement rather than disbarment as things now stand.
5. What accounts for Giuliani’s rather spectacular failure with law firms?
I have spoken with partners at three firms where Rudy spent time. The knocks on him were consistent: he was quick on the trigger with legal advice and tended to see almost everything through a partisan political prism. He was viewed as a loose cannon who had little concern for the law firms he worked with and rarely seemed to appreciate his partners or deal with them fairly. Some of the firms were frightened by the figures abroad he tried to develop as clients, including some figures with organized crime backgrounds. He didn’t want to submit to the normal intake process that firms have for identifying and filtering out risks.
Generally people with illustrious public careers go to a prominent firm, make a lot of money, and work fairly quietly as the firm’s éminence grise. Not so Rudy. The firms were generally very worried about the risks he took and the exposure he created. That explains why he bounced from firm to firm and wound up on his own. When he left public office and was looking for law firms, I know that several firms made intentionally “low ball” offers to him. They wanted to preserve a positive rapport with Rudy, but they really didn’t want him to join their firm. That broadly reflected an assessment that he was a political star, but not really a very good lawyer, and that his quixotic, unpredictable nature was going to land him in trouble.
6. It seems that former President Trump and many of his minions may escape any accountability for their misbehavior while in office, some of which may have been illegal. What about Giuliani? What lies in his future? Will he skate or might he face some consequences for his acts?
It’s clear enough at this point that William Barr, as attorney general, shut down efforts to subpoena Rudy in order at least to preserve evidence. With the change in administration, I understand that the Southern District of New York was told that their case could proceed in the normal form, meaning that the holdover Trump-era U.S. Attorney, Audrey Strauss, got a green light to do what she thought appropriate. That explains the raids that the FBI carried out yesterday.
We all know about the Ukraine business, which has already produced criminal charges against two of Giuliani’s associates. My understanding is that there are several other matters floating around, mostly relating to Rudy’s representation of foreign interests without registration or disclosure. And we still have the issues from 2016, when Rudy repeatedly appeared on Rupert Murdoch media outlets talking about FBI investigations into Anthony Weiner, Hillary Clinton, the Clinton Foundation and other matters. He claimed he had access to internal FBI investigations and publicized them. Not a crime for Rudy to do this, but likely a crime for some FBI agents to have shared this information. So there’s a lot there, but we don’t know enough at this point to venture a useful guess about whether he will face criminal charges. Whether he will hold his law license is another matter though. That looks like a rather long shot for Rudy at this point.